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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (219) Show 219 proteins XML

enzymes (219) Show 219 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:20 UTC

HMDB ID

HMDB0001487

Secondary Accession Numbers

HMDB01487

Metabolite Identification

Common Name

NADH

Description

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen) respectively. NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH. NAD (or nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be either converted into ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it via cellular respiration. NAD is a coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by a pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). NADP is formed through the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309042000232D          

 44 48  0  0  0  0            999 V2000
 9995.5688 9998.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3578 9998.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8653 9999.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5818 9999.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2961 9999.9046    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.0167 9999.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7302 9999.9168    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.4459 9999.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1573 9999.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6358 9998.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.4258 9998.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.0717 9999.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.7873 9999.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10007.0717 9998.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.317810000.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.142710000.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.882710000.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.707610000.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5378 9999.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8704 9999.5142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.1253 9998.7296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.9503 9998.7296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.2052 9999.5142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.4809 9999.9854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0684 9998.7158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.8934 9998.7158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1483 9999.5004    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.351610000.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.637110001.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.922610000.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.9225 9999.9170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.6370 9999.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.3516 9999.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.033010000.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6975 9999.5178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1825 9998.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0029 9998.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3385 9999.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.853510000.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.548010000.9388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1231 9999.9450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.123110000.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.338610001.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7905 9999.4600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  2  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  2  0  0  0  0
  8  9  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 27  1  0  0  0  0
 25  1  1  1  0  0  0
 27  3  1  6  0  0  0
 26  2  1  1  0  0  0
 20  9  1  1  0  0  0
 22 11  1  6  0  0  0
 21 10  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 32 33  2  0  0  0  0
 33 28  1  0  0  0  0
 33 12  1  0  0  0  0
 38 39  2  0  0  0  0
 39 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 34 40  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
 41 42  1  0  0  0  0
 38 41  1  0  0  0  0
 44 41  1  6  0  0  0
 44 25  1  0  0  0  0
 24 44  1  0  0  0  0
  7 16  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 31  1  1  0  0  0
M  END

HMDB0001487
     RDKit          3D
NADH
 73 77  0  0  0  0  0  0  0  0999 V2000
   10.3397    1.2977   -1.0927 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4943   -0.0219   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284   -0.5421   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3274   -0.7442   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1164   -0.2110   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9572   -0.8874    0.3283 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6666   -0.2399    0.3103 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6390   -1.0838    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -0.4046    0.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3988   -1.4329   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -0.7156   -0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.7767   -0.7130 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.3028   -2.6433   -1.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -2.7769    0.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8831   -0.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -0.0318    0.4149 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9958   -1.0212    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    0.9937    0.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.8086    0.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867    1.7763   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130    2.5157   -1.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3548    1.5866   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3916    1.6137   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0070    0.3101   -0.3041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3514   -0.8563   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2528   -1.8305   -0.1855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4674   -1.3108    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7065   -1.8410    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8444   -3.2456    0.3206 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7856   -1.0569    0.4092 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6215    0.2852    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4025    0.8276    0.0994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3081    0.0651   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7985    2.1094    0.8400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7807    2.8112    1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7622    3.1036    0.3246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4183    4.3075    0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    0.3701   -0.9572 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5676    1.7177   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2809    0.1604   -1.1197 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9349    1.3316   -1.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1312   -2.2148    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -2.7905    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5150   -2.1186    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8383    2.0799   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7208    1.4866   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0224    0.8091   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250    0.6620    0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    0.2184    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -2.0492    0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.1074   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -2.3356    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    1.3901    0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.4605   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    1.1987   -1.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855    3.2854   -1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1776    2.3457   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -0.9878   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9221   -3.7464    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8679   -3.7935   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5015    0.8973    0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.3218    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507    2.4346    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119    3.1827    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    4.4017   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    0.0097   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    2.2860   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4699   -0.6800   -1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254    1.2977   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2372   -2.7509    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4057   -3.8222    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0560   -2.7566   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2127   -2.0486    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 23 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
  9 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
  6 42  1  0
 42 43  2  0
 43 44  1  0
 44  4  1  0
 40  7  1  0
 36 21  1  0
 33 24  1  0
 33 27  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  0
  7 48  1  1
  9 49  1  1
 10 50  1  0
 10 51  1  0
 14 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  6
 23 57  1  6
 25 58  1  0
 29 59  1  0
 29 60  1  0
 31 61  1  0
 34 62  1  1
 35 63  1  0
 36 64  1  1
 37 65  1  0
 38 66  1  6
 39 67  1  0
 40 68  1  6
 41 69  1  0
 42 70  1  0
 43 71  1  0
 44 72  1  0
 44 73  1  0
M  END


  Mrv1652309042000232D          

 44 48  0  0  0  0            999 V2000
 9995.5688 9998.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3578 9998.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8653 9999.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5818 9999.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2961 9999.9046    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.0167 9999.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7302 9999.9168    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10001.4459 9999.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1573 9999.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6358 9998.0583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.4258 9998.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.0717 9999.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.7873 9999.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10007.0717 9998.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.317810000.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.142710000.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.882710000.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.707610000.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5378 9999.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8704 9999.5142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.1253 9998.7296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.9503 9998.7296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.2052 9999.5142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.4809 9999.9854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0684 9998.7158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.8934 9998.7158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1483 9999.5004    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.351610000.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.637110001.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.922610000.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.9225 9999.9170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.6370 9999.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.3516 9999.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.033010000.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6975 9999.5178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1825 9998.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0029 9998.9365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3385 9999.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.853510000.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.548010000.9388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1231 9999.9450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.123110000.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.338610001.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7905 9999.4600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  2  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  2  0  0  0  0
  8  9  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 27  1  0  0  0  0
 25  1  1  1  0  0  0
 27  3  1  6  0  0  0
 26  2  1  1  0  0  0
 20  9  1  1  0  0  0
 22 11  1  6  0  0  0
 21 10  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 32 33  2  0  0  0  0
 33 28  1  0  0  0  0
 33 12  1  0  0  0  0
 38 39  2  0  0  0  0
 39 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 34 40  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
 41 42  1  0  0  0  0
 38 41  1  0  0  0  0
 44 41  1  6  0  0  0
 44 25  1  0  0  0  0
 24 44  1  0  0  0  0
  7 16  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 31  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001487

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
BOPGDPNILDQYTO-NNYOXOHSSA-N

> <FORMULA>
C21H29N7O14P2

> <MOLECULAR_WEIGHT>
665.441

> <EXACT_MASS>
665.124771695

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.65419831221258

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid

> <ALOGPS_LOGP>
-1.45

> <JCHEM_LOGP>
-5.855536205936978

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.187368832858877

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536409122750466

> <JCHEM_PKA_STRONGEST_BASIC>
4.009033959582867

> <JCHEM_POLAR_SURFACE_AREA>
317.61999999999995

> <JCHEM_REFRACTIVITY>
142.99969999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
NADH

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001487
     RDKit          3D
NADH
 73 77  0  0  0  0  0  0  0  0999 V2000
   10.3397    1.2977   -1.0927 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4943   -0.0219   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284   -0.5421   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3274   -0.7442   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1164   -0.2110   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9572   -0.8874    0.3283 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6666   -0.2399    0.3103 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6390   -1.0838    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -0.4046    0.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3988   -1.4329   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -0.7156   -0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.7767   -0.7130 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.3028   -2.6433   -1.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -2.7769    0.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8831   -0.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -0.0318    0.4149 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9958   -1.0212    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    0.9937    0.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.8086    0.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867    1.7763   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130    2.5157   -1.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3548    1.5866   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3916    1.6137   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0070    0.3101   -0.3041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3514   -0.8563   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2528   -1.8305   -0.1855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4674   -1.3108    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7065   -1.8410    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8444   -3.2456    0.3206 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7856   -1.0569    0.4092 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6215    0.2852    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4025    0.8276    0.0994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3081    0.0651   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7985    2.1094    0.8400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7807    2.8112    1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7622    3.1036    0.3246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4183    4.3075    0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    0.3701   -0.9572 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5676    1.7177   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2809    0.1604   -1.1197 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9349    1.3316   -1.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1312   -2.2148    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -2.7905    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5150   -2.1186    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8383    2.0799   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7208    1.4866   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0224    0.8091   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250    0.6620    0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    0.2184    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -2.0492    0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.1074   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -2.3356    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    1.3901    0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.4605   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    1.1987   -1.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855    3.2854   -1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1776    2.3457   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -0.9878   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9221   -3.7464    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8679   -3.7935   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5015    0.8973    0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.3218    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507    2.4346    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119    3.1827    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    4.4017   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    0.0097   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    2.2860   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4699   -0.6800   -1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254    1.2977   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2372   -2.7509    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4057   -3.8222    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0560   -2.7566   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2127   -2.0486    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 23 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
  9 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
  6 42  1  0
 42 43  2  0
 43 44  1  0
 44  4  1  0
 40  7  1  0
 36 21  1  0
 33 24  1  0
 33 27  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  0
  7 48  1  1
  9 49  1  1
 10 50  1  0
 10 51  1  0
 14 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  6
 23 57  1  6
 25 58  1  0
 29 59  1  0
 29 60  1  0
 31 61  1  0
 34 62  1  1
 35 63  1  0
 36 64  1  1
 37 65  1  0
 38 66  1  6
 39 67  1  0
 40 68  1  6
 41 69  1  0
 42 70  1  0
 43 71  1  0
 44 72  1  0
 44 73  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8658.3958663.031   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8661.7358663.015   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8662.6828666.489   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8664.0198665.717   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8665.3538666.489   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8666.6988665.743   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0    8668.0308666.511   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0    8669.3668665.743   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8670.6948666.511   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8671.5878663.042   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8674.9288663.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8679.8678665.766   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8681.2038666.535   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0    8679.8678664.227   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8667.2608667.846   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8668.8008667.846   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8664.5818667.823   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8666.1218667.823   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8673.2718666.665   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8672.0258665.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.5018664.295   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8674.0418664.295   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.5168665.760   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8660.0988666.639   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8659.3288664.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8660.8688664.269   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8661.3438665.734   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8678.5238668.052   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8677.1898668.822   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8675.8568668.052   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0    8675.8558666.512   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0    8677.1898665.742   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8678.5238666.512   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8653.6628667.173   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0    8653.0358665.767   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0    8653.9418664.521   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0    8655.4728664.681   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0    8656.0998666.088   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8655.1938667.334   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0    8652.7568668.419   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0    8657.5638666.564   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0    8657.5638668.104   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0    8656.0998668.580   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0    8658.8098665.659   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3    4   27                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   15   16                                             
CONECT    8    7    9                                                       
CONECT    9    8   20                                                       
CONECT   10   21                                                            
CONECT   11   22                                                            
CONECT   12   13   14   33                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17    5                                                            
CONECT   18    5                                                            
CONECT   19   20   23                                                       
CONECT   20   21   19    9                                                  
CONECT   21   20   22   10                                                  
CONECT   22   21   23   11                                                  
CONECT   23   22   19   31                                                  
CONECT   24   27   44                                                       
CONECT   25   26    1   44                                                  
CONECT   26   25   27    2                                                  
CONECT   27   26   24    3                                                  
CONECT   28   29   33                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   23                                                  
CONECT   32   33   31                                                       
CONECT   33   32   28   12                                                  
CONECT   34   39   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   39   37   41                                                  
CONECT   39   38   34   43                                                  
CONECT   40   34                                                            
CONECT   41   42   38   44                                                  
CONECT   42   43   41                                                       
CONECT   43   42   39                                                       
CONECT   44   41   25   24                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

COMPND    HMDB0001487
HETATM    1  N1  UNL     1      10.340   1.298  -1.093  1.00  0.00           N  
HETATM    2  C1  UNL     1      10.494  -0.022  -0.621  1.00  0.00           C  
HETATM    3  O1  UNL     1      11.628  -0.542  -0.624  1.00  0.00           O  
HETATM    4  C2  UNL     1       9.327  -0.744  -0.143  1.00  0.00           C  
HETATM    5  C3  UNL     1       8.116  -0.211  -0.131  1.00  0.00           C  
HETATM    6  N2  UNL     1       6.957  -0.887   0.328  1.00  0.00           N  
HETATM    7  C4  UNL     1       5.667  -0.240   0.310  1.00  0.00           C  
HETATM    8  O2  UNL     1       4.639  -1.084   0.649  1.00  0.00           O  
HETATM    9  C5  UNL     1       3.485  -0.405   0.282  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.399  -1.433  -0.005  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.257  -0.716  -0.370  1.00  0.00           O  
HETATM   12  P1  UNL     1      -0.023  -1.777  -0.713  1.00  0.00           P  
HETATM   13  O4  UNL     1       0.303  -2.643  -1.908  1.00  0.00           O  
HETATM   14  O5  UNL     1      -0.276  -2.777   0.620  1.00  0.00           O  
HETATM   15  O6  UNL     1      -1.409  -0.883  -0.994  1.00  0.00           O  
HETATM   16  P2  UNL     1      -1.801  -0.032   0.415  1.00  0.00           P  
HETATM   17  O7  UNL     1      -1.996  -1.021   1.535  1.00  0.00           O  
HETATM   18  O8  UNL     1      -0.524   0.994   0.869  1.00  0.00           O  
HETATM   19  O9  UNL     1      -3.224   0.809   0.182  1.00  0.00           O  
HETATM   20  C7  UNL     1      -3.087   1.776  -0.835  1.00  0.00           C  
HETATM   21  C8  UNL     1      -4.413   2.516  -1.009  1.00  0.00           C  
HETATM   22  O10 UNL     1      -5.355   1.587  -1.352  1.00  0.00           O  
HETATM   23  C9  UNL     1      -6.392   1.614  -0.458  1.00  0.00           C  
HETATM   24  N3  UNL     1      -7.007   0.310  -0.304  1.00  0.00           N  
HETATM   25  C10 UNL     1      -6.351  -0.856  -0.379  1.00  0.00           C  
HETATM   26  N4  UNL     1      -7.253  -1.830  -0.186  1.00  0.00           N  
HETATM   27  C11 UNL     1      -8.467  -1.311   0.010  1.00  0.00           C  
HETATM   28  C12 UNL     1      -9.707  -1.841   0.247  1.00  0.00           C  
HETATM   29  N5  UNL     1      -9.844  -3.246   0.321  1.00  0.00           N  
HETATM   30  N6  UNL     1     -10.786  -1.057   0.409  1.00  0.00           N  
HETATM   31  C13 UNL     1     -10.622   0.285   0.333  1.00  0.00           C  
HETATM   32  N7  UNL     1      -9.403   0.828   0.099  1.00  0.00           N  
HETATM   33  C14 UNL     1      -8.308   0.065  -0.066  1.00  0.00           C  
HETATM   34  C15 UNL     1      -5.799   2.109   0.840  1.00  0.00           C  
HETATM   35  O11 UNL     1      -6.781   2.811   1.544  1.00  0.00           O  
HETATM   36  C16 UNL     1      -4.762   3.104   0.325  1.00  0.00           C  
HETATM   37  O12 UNL     1      -5.418   4.308   0.114  1.00  0.00           O  
HETATM   38  C17 UNL     1       3.793   0.370  -0.957  1.00  0.00           C  
HETATM   39  O13 UNL     1       3.568   1.718  -0.704  1.00  0.00           O  
HETATM   40  C18 UNL     1       5.281   0.160  -1.120  1.00  0.00           C  
HETATM   41  O14 UNL     1       5.935   1.332  -1.491  1.00  0.00           O  
HETATM   42  C19 UNL     1       7.131  -2.215   0.800  1.00  0.00           C  
HETATM   43  C20 UNL     1       8.307  -2.790   0.811  1.00  0.00           C  
HETATM   44  C21 UNL     1       9.515  -2.119   0.344  1.00  0.00           C  
HETATM   45  H1  UNL     1      10.838   2.080  -0.639  1.00  0.00           H  
HETATM   46  H2  UNL     1       9.721   1.487  -1.902  1.00  0.00           H  
HETATM   47  H3  UNL     1       8.022   0.809  -0.500  1.00  0.00           H  
HETATM   48  H4  UNL     1       5.625   0.662   0.950  1.00  0.00           H  
HETATM   49  H5  UNL     1       3.164   0.218   1.139  1.00  0.00           H  
HETATM   50  H6  UNL     1       2.180  -2.049   0.885  1.00  0.00           H  
HETATM   51  H7  UNL     1       2.727  -2.107  -0.825  1.00  0.00           H  
HETATM   52  H8  UNL     1       0.098  -2.336   1.420  1.00  0.00           H  
HETATM   53  H9  UNL     1      -0.085   1.390   0.097  1.00  0.00           H  
HETATM   54  H10 UNL     1      -2.255   2.460  -0.650  1.00  0.00           H  
HETATM   55  H11 UNL     1      -2.848   1.199  -1.758  1.00  0.00           H  
HETATM   56  H12 UNL     1      -4.285   3.285  -1.788  1.00  0.00           H  
HETATM   57  H13 UNL     1      -7.178   2.346  -0.745  1.00  0.00           H  
HETATM   58  H14 UNL     1      -5.277  -0.988  -0.563  1.00  0.00           H  
HETATM   59  H15 UNL     1      -9.922  -3.746   1.213  1.00  0.00           H  
HETATM   60  H16 UNL     1      -9.868  -3.794  -0.567  1.00  0.00           H  
HETATM   61  H17 UNL     1     -11.502   0.897   0.466  1.00  0.00           H  
HETATM   62  H18 UNL     1      -5.325   1.322   1.435  1.00  0.00           H  
HETATM   63  H19 UNL     1      -6.951   2.435   2.430  1.00  0.00           H  
HETATM   64  H20 UNL     1      -3.912   3.183   1.006  1.00  0.00           H  
HETATM   65  H21 UNL     1      -5.749   4.402  -0.817  1.00  0.00           H  
HETATM   66  H22 UNL     1       3.230   0.010  -1.843  1.00  0.00           H  
HETATM   67  H23 UNL     1       3.907   2.286  -1.449  1.00  0.00           H  
HETATM   68  H24 UNL     1       5.470  -0.680  -1.798  1.00  0.00           H  
HETATM   69  H25 UNL     1       6.125   1.298  -2.463  1.00  0.00           H  
HETATM   70  H26 UNL     1       6.237  -2.751   1.160  1.00  0.00           H  
HETATM   71  H27 UNL     1       8.406  -3.822   1.183  1.00  0.00           H  
HETATM   72  H28 UNL     1      10.056  -2.757  -0.398  1.00  0.00           H  
HETATM   73  H29 UNL     1      10.213  -2.049   1.223  1.00  0.00           H  
CONECT    1    2   45   46
CONECT    2    3    3    4
CONECT    4    5    5   44
CONECT    5    6   47
CONECT    6    7   42
CONECT    7    8   40   48
CONECT    8    9
CONECT    9   10   38   49
CONECT   10   11   50   51
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   52
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   53
CONECT   19   20
CONECT   20   21   54   55
CONECT   21   22   36   56
CONECT   22   23
CONECT   23   24   34   57
CONECT   24   25   33
CONECT   25   26   26   58
CONECT   26   27
CONECT   27   28   28   33
CONECT   28   29   30
CONECT   29   59   60
CONECT   30   31   31
CONECT   31   32   61
CONECT   32   33   33
CONECT   34   35   36   62
CONECT   35   63
CONECT   36   37   64
CONECT   37   65
CONECT   38   39   40   66
CONECT   39   67
CONECT   40   41   68
CONECT   41   69
CONECT   42   43   43   70
CONECT   43   44   71
CONECT   44   72   73
END

HMDB0001487
     RDKit          3D
NADH
 73 77  0  0  0  0  0  0  0  0999 V2000
   10.3397    1.2977   -1.0927 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4943   -0.0219   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6284   -0.5421   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3274   -0.7442   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1164   -0.2110   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9572   -0.8874    0.3283 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6666   -0.2399    0.3103 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6390   -1.0838    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4851   -0.4046    0.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3988   -1.4329   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -0.7156   -0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -1.7767   -0.7130 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.3028   -2.6433   -1.9081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -2.7769    0.6197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8831   -0.9942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8013   -0.0318    0.4149 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9958   -1.0212    1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    0.9937    0.8689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239    0.8086    0.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0867    1.7763   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130    2.5157   -1.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3548    1.5866   -1.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3916    1.6137   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0070    0.3101   -0.3041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3514   -0.8563   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2528   -1.8305   -0.1855 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4674   -1.3108    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7065   -1.8410    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8444   -3.2456    0.3206 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7856   -1.0569    0.4092 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6215    0.2852    0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4025    0.8276    0.0994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3081    0.0651   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7985    2.1094    0.8400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7807    2.8112    1.5437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7622    3.1036    0.3246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4183    4.3075    0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7933    0.3701   -0.9572 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5676    1.7177   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2809    0.1604   -1.1197 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9349    1.3316   -1.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1312   -2.2148    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3066   -2.7905    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5150   -2.1186    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8383    2.0799   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7208    1.4866   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0224    0.8091   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250    0.6620    0.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    0.2184    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1804   -2.0492    0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -2.1074   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -2.3356    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    1.3901    0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    2.4605   -0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    1.1987   -1.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855    3.2854   -1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1776    2.3457   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2769   -0.9878   -0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9221   -3.7464    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8679   -3.7935   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5015    0.8973    0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    1.3218    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507    2.4346    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119    3.1827    1.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    4.4017   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302    0.0097   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066    2.2860   -1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4699   -0.6800   -1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1254    1.2977   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2372   -2.7509    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4057   -3.8222    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0560   -2.7566   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2127   -2.0486    1.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 23 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
  9 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
  6 42  1  0
 42 43  2  0
 43 44  1  0
 44  4  1  0
 40  7  1  0
 36 21  1  0
 33 24  1  0
 33 27  1  0
  1 45  1  0
  1 46  1  0
  5 47  1  0
  7 48  1  1
  9 49  1  1
 10 50  1  0
 10 51  1  0
 14 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  6
 23 57  1  6
 25 58  1  0
 29 59  1  0
 29 60  1  0
 31 61  1  0
 34 62  1  1
 35 63  1  0
 36 64  1  1
 37 65  1  0
 38 66  1  6
 39 67  1  0
 40 68  1  6
 41 69  1  0
 42 70  1  0
 43 71  1  0
 44 72  1  0
 44 73  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,4-DIHYDRONICOTINAMIDE adenine dinucleotide	ChEBI
DPNH	ChEBI
Nicotinamide adenine dinucleotide (reduced)	ChEBI
Reduced nicotinamide adenine dinucleotide	ChEBI
b-DPNH	HMDB
b-NADH	HMDB
beta-DPNH	HMDB
beta-NADH	HMDB
Dihydrocodehydrogenase I	HMDB
Dihydrocozymase	HMDB
Dihydronicotinamide adenine dinucleotide	HMDB
Dihydronicotinamide mononucleotide	HMDB
ENADA	HMDB
NADH2	HMDB
Reduced codehydrogenase I	HMDB
Reduced diphosphopyridine nucleotide	HMDB
Reduced nicotinamide adenine diphosphate	HMDB
Reduced nicotinamide-adenine dinucleotide	HMDB
Nadide	HMDB
Coenzyme I	HMDB
DPN	HMDB
Diphosphopyridine nucleotide	HMDB
Nicotinamide adenine dinucleotide	HMDB
Nicotinamide-adenine dinucleotide	HMDB
NAD	HMDB
Nucleotide, diphosphopyridine	HMDB
Adenine dinucleotide, dihydronicotinamide	HMDB
Dinucleotide, dihydronicotinamide adenine	HMDB
Dinucleotide, nicotinamide-adenine	HMDB

Chemical Formula

C₂₁H₂₉N₇O₁₄P₂

Average Molecular Weight

665.441

Monoisotopic Molecular Weight

665.124771695

IUPAC Name

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid

Traditional Name

NADH

CAS Registry Number

58-68-4

SMILES

NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

BOPGDPNILDQYTO-NNYOXOHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
N-substituted nicotinamide
Organic pyrophosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Dihydropyridine
Aminopyrimidine
Pyrimidine
Imidolactam
Monosaccharide
N-substituted imidazole
Alkyl phosphate
Phosphoric acid ester
Hydropyridine
Organic phosphoric acid derivative
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Vinylogous amide
Azole
Amino acid or derivatives
Primary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Enamine
Azacycle
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Primary amine
Amine
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NAD (CHEBI:16908 )
NAD(P)H (CHEBI:16908 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

2-ketoglutarate dehydrogenase complex deficiency
3-methylglutaconic aciduria type i
3-phosphoglycerate dehydrogenase deficiency

Acute intermittent porphyria (PMID: 10905759 , PMID: 10905759 , PMID: 18804642 , +3

Source	Link
Pubmed	PMID: 10905759
Pubmed	PMID: 10905759
Pubmed	PMID: 18804642
Pubmed	PMID: 19309105
Pubmed	PMID: 23908454
Pubmed	PMID: 27012787

)

Adenosine deaminase deficiency

Adenylosuccinate lyase deficiency (PMID: 11805243 , PMID: 12535838 , PMID: 15571235 , +2

Source	Link
Pubmed	PMID: 11805243
Pubmed	PMID: 12535838
Pubmed	PMID: 15571235
Pubmed	PMID: 25037050
Pubmed	PMID: 27543620

)

Alkaptonuria (PMID: 25956497 )
Carnosinemia

Cystinosis (PMID: 12457401 , PMID: 12503102 , PMID: 19787747 , +3

Source	Link
Pubmed	PMID: 12457401
Pubmed	PMID: 12503102
Pubmed	PMID: 19787747
Pubmed	PMID: 2017228
Pubmed	PMID: 3276734
Pubmed	PMID: 8787802

)

Dimethylglycine dehydrogenase deficiency

Ethylmalonic encephalopathy (PMID: 10731506 , PMID: 27012787 , PMID: 3571488 , +12

Source	Link
Pubmed	PMID: 10731506
Pubmed	PMID: 27012787
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 8087979
Pubmed	PMID: 31963255
Pubmed	PMID: 16828325
Pubmed	PMID: 10197568
Pubmed	PMID: 7609451
Pubmed	PMID: 7609451
Pubmed	PMID: 2026685
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 24023812

)

Gaba-transaminase deficiency
Galactosemia (PMID: 6433315 , PMID: 7119120 , PMID: 7119120 )

Glycerol kinase deficiency (PMID: 14708889 , PMID: 32966057 , PMID: 6299616 , +2

Source	Link
Pubmed	PMID: 14708889
Pubmed	PMID: 32966057
Pubmed	PMID: 6299616
Pubmed	PMID: 9007327
Pubmed	PMID: 9007327

)

Glycine n-methyltransferase deficiency

Hawkinsinuria (PMID: 10412819 , PMID: 11281457 , PMID: 11978597 , +3

Source	Link
Pubmed	PMID: 10412819
Pubmed	PMID: 11281457
Pubmed	PMID: 11978597
Pubmed	PMID: 25754623
Pubmed	PMID: 26226126
Pubmed	PMID: 26226126

)

Histidinemia (PMID: 1146783 , PMID: 14044449 , PMID: 12297216 , +15

Source	Link
Pubmed	PMID: 1146783
Pubmed	PMID: 14044449
Pubmed	PMID: 12297216
Pubmed	PMID: 21359215
Pubmed	PMID: 17349089
Pubmed	PMID: 24027187
Pubmed	PMID: 1146783
Pubmed	PMID: 15168722
Pubmed	PMID: 14044449
Pubmed	PMID: 18953024
Pubmed	PMID: 17068770
Pubmed	PMID: 6198473
Pubmed	PMID: 22546835
Pubmed	PMID: 14992292
Pubmed	PMID: 24130822
Pubmed	PMID: 7729054
Pubmed	PMID: 4030756
Pubmed	PMID: 4030756

)

Methionine adenosyltransferase deficiency (PMID: 8745393 , PMID: 27207470 , PMID: 27294788 , +6

Source	Link
Pubmed	PMID: 8745393
Pubmed	PMID: 27207470
Pubmed	PMID: 27294788
Pubmed	PMID: 21559159
Pubmed	PMID: 21910240
Pubmed	PMID: 23108202
Pubmed	PMID: 7229751
Pubmed	PMID: 20549362
Pubmed	PMID: 25754623

)

Methylmalonate semialdehyde dehydrogenase deficiency (PMID: 3939535 , PMID: 3939535 )
Myoadenylate deaminase deficiency (PMID: 11978597 )

Purine nucleoside phosphorylase deficiency (PMID: 16139832 , PMID: 32966057 , PMID: 9663253 , +7

Source	Link
Pubmed	PMID: 16139832
Pubmed	PMID: 32966057
Pubmed	PMID: 9663253
Pubmed	PMID: 9607216
Pubmed	PMID: 8595732
Pubmed	PMID: 3818951
Pubmed	PMID: 8595732
Pubmed	PMID: 9129323
Pubmed	PMID: 28157703
Pubmed	PMID: 24023812

)

Pyruvate dehydrogenase complex deficiency

Sarcosinemia (PMID: 24341803 , PMID: 17436247 , PMID: 8739971 , +49

Source	Link
Pubmed	PMID: 24341803
Pubmed	PMID: 17436247
Pubmed	PMID: 8739971
Pubmed	PMID: 432003
Pubmed	PMID: 2420598
Pubmed	PMID: 2420598
Pubmed	PMID: 21359215
Pubmed	PMID: 22800120
Pubmed	PMID: 32966057
Pubmed	PMID: 23430553
Pubmed	PMID: 16890503
Pubmed	PMID: 28278231
Pubmed	PMID: 14454131
Pubmed	PMID: 27294788
Pubmed	PMID: 22007635
Pubmed	PMID: 23430553
Pubmed	PMID: 21113737
Pubmed	PMID: 17068770
Pubmed	PMID: 15911239
Pubmed	PMID: 6198473
Pubmed	PMID: 22546835
Pubmed	PMID: 7595563
Pubmed	PMID: 20803002
Pubmed	PMID: 19033659
Pubmed	PMID: 24023812
Pubmed	PMID: 3168222
Pubmed	PMID: 19033659
Pubmed	PMID: 6321058
Pubmed	PMID: 31775291
Pubmed	PMID: 27012787
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 17474139
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 4434100
Pubmed	PMID: 12297216
Pubmed	PMID: 22024767
Pubmed	PMID: 20549362
Pubmed	PMID: 12834252
Pubmed	PMID: 18502700
Pubmed	PMID: 16390611
Pubmed	PMID: 26960553
Pubmed	PMID: 25670064
Pubmed	PMID: 15992788
Pubmed	PMID: 19309105
Pubmed	PMID: 30830347
Pubmed	PMID: 6207480
Pubmed	PMID: 9323574
Pubmed	PMID: 10102904
Pubmed	PMID: 7694037

)

Sepiapterin reductase deficiency
Tyrosinemia

Nontypified gene mutations

Organic acidemia

3-hydroxy-3-methylglutaryl-coa lyase deficiency
3-hydroxyisobutyric aciduria
Beta-ketothiolase deficiency

Fumarase deficiency (PMID: 24182348 , PMID: 24182348 , PMID: 26078636 , +28

Source	Link
Pubmed	PMID: 24182348
Pubmed	PMID: 24182348
Pubmed	PMID: 26078636
Pubmed	PMID: 4837567
Pubmed	PMID: 14708889
Pubmed	PMID: 8087979
Pubmed	PMID: 26078636
Pubmed	PMID: 12383482
Pubmed	PMID: 31963255
Pubmed	PMID: 12376931
Pubmed	PMID: 2026685
Pubmed	PMID: 6616883
Pubmed	PMID: 16972175
Pubmed	PMID: 18953024
Pubmed	PMID: 2242313
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 21910240
Pubmed	PMID: 28070528
Pubmed	PMID: 22308371
Pubmed	PMID: 24023812
Pubmed	PMID: 27012787
Pubmed	PMID: 9573551
Pubmed	PMID: 27504266
Pubmed	PMID: 30817767
Pubmed	PMID: 1640293
Pubmed	PMID: 25012580
Pubmed	PMID: 21389975
Pubmed	PMID: 11067816
Pubmed	PMID: 21388201
Pubmed	PMID: 24341803

)

Isovaleric acidemia (PMID: 2000815 , PMID: 9368807 , PMID: 14608088 , +33

Source	Link
Pubmed	PMID: 2000815
Pubmed	PMID: 9368807
Pubmed	PMID: 14608088
Pubmed	PMID: 8412012
Pubmed	PMID: 21359215
Pubmed	PMID: 24740205
Pubmed	PMID: 18953024
Pubmed	PMID: 32966057
Pubmed	PMID: 20671299
Pubmed	PMID: 27329611
Pubmed	PMID: 27329611
Pubmed	PMID: 1246461
Pubmed	PMID: 1246461
Pubmed	PMID: 24023812
Pubmed	PMID: 11978597
Pubmed	PMID: 17069347
Pubmed	PMID: 17313719
Pubmed	PMID: 21185973
Pubmed	PMID: 18633173
Pubmed	PMID: 27355821
Pubmed	PMID: 10022638
Pubmed	PMID: 18203893
Pubmed	PMID: 24801555
Pubmed	PMID: 11593343
Pubmed	PMID: 10197568
Pubmed	PMID: 7609451
Pubmed	PMID: 12837870
Pubmed	PMID: 12837870
Pubmed	PMID: 25004141
Pubmed	PMID: 20143319
Pubmed	PMID: 14634727
Pubmed	PMID: 2361977
Pubmed	PMID: 18953024
Pubmed	PMID: 24789758
Pubmed	PMID: 22007635
Pubmed	PMID: 22061338

)

Malonyl-coa decarboxylase deficiency

Maple syrup urine disease (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +59

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 19309105
Pubmed	PMID: 17022649
Pubmed	PMID: 25733631
Pubmed	PMID: 32966057
Pubmed	PMID: 25536744
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 6422161
Pubmed	PMID: 10102904
Pubmed	PMID: 21736852
Pubmed	PMID: 17349089
Pubmed	PMID: 16601883
Pubmed	PMID: 9246418
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 5727921
Pubmed	PMID: 5472370
Pubmed	PMID: 30830347
Pubmed	PMID: 18088602
Pubmed	PMID: 22956686
Pubmed	PMID: 27294788
Pubmed	PMID: 18088602
Pubmed	PMID: 19217890
Pubmed	PMID: 9732980
Pubmed	PMID: 18004736
Pubmed	PMID: 11052553
Pubmed	PMID: 15899597
Pubmed	PMID: 5018656
Pubmed	PMID: 21505807
Pubmed	PMID: 25754623
Pubmed	PMID: 6422161
Pubmed	PMID: 23430924
Pubmed	PMID: 10508118

)

Propionic acidemia (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +65

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 17022649
Pubmed	PMID: 25733631
Pubmed	PMID: 32966057
Pubmed	PMID: 19309105
Pubmed	PMID: 25536744
Pubmed	PMID: 23062437
Pubmed	PMID: 21704015
Pubmed	PMID: 28853722
Pubmed	PMID: 23705938
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 2226555
Pubmed	PMID: 6616873
Pubmed	PMID: 10102904
Pubmed	PMID: 21736852
Pubmed	PMID: 17349089
Pubmed	PMID: 16601883
Pubmed	PMID: 9246418
Pubmed	PMID: 9667231
Pubmed	PMID: 21841779
Pubmed	PMID: 9439441
Pubmed	PMID: 11067816
Pubmed	PMID: 16139832
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 5727921
Pubmed	PMID: 5472370
Pubmed	PMID: 30830347
Pubmed	PMID: 28028301
Pubmed	PMID: 9187477
Pubmed	PMID: 26910390
Pubmed	PMID: 7131143
Pubmed	PMID: 19217890
Pubmed	PMID: 9732980
Pubmed	PMID: 8087979
Pubmed	PMID: 23269817
Pubmed	PMID: 15899597
Pubmed	PMID: 11052553
Pubmed	PMID: 18004736

)

Succinic semialdehyde dehydrogenase deficiency (PMID: 11978597 , PMID: 12127325 , PMID: 12127325 , +1

Source	Link
Pubmed	PMID: 11978597
Pubmed	PMID: 12127325
Pubmed	PMID: 12127325
Pubmed	PMID: 8087979

)

Urea cycle disorder

Argininemia (PMID: 26971250 , PMID: 11281457 , PMID: 28659245 , +14

Source	Link
Pubmed	PMID: 26971250
Pubmed	PMID: 11281457
Pubmed	PMID: 28659245
Pubmed	PMID: 2044610
Pubmed	PMID: 28028301
Pubmed	PMID: 28132756
Pubmed	PMID: 2311630
Pubmed	PMID: 27294788
Pubmed	PMID: 11092761
Pubmed	PMID: 26066683
Pubmed	PMID: 25691415
Pubmed	PMID: 7595563
Pubmed	PMID: 2311630
Pubmed	PMID: 26123990
Pubmed	PMID: 31963255
Pubmed	PMID: 16139832
Pubmed	PMID: 30817767

)

Argininosuccinic aciduria
Carbamoyl phosphate synthetase deficiency
Citrullinemia type i

Carnosinuria (PMID: 24023812 , PMID: 2674258 , PMID: 32966057 )

Circulatory system disorder

Blood and lymphatic system disorder

Hyperglycinemia

Hypermethioninemia (PMID: 15024124 , PMID: 8745393 , PMID: 27207470 , +6

Source	Link
Pubmed	PMID: 15024124
Pubmed	PMID: 8745393
Pubmed	PMID: 27207470
Pubmed	PMID: 27294788
Pubmed	PMID: 21559159
Pubmed	PMID: 21910240
Pubmed	PMID: 23108202
Pubmed	PMID: 23770102
Pubmed	PMID: 17349089

)

Disposition

Biological location

Cellular substructure

Organelle

Non-excretory biofluid

Blood

Organ

Cell

Hematocyte

Platelet

Tissue

Muscle tissue

Skeletal muscle

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Nuts

Cocoa and cocoa products

Cocoa

Cocoa bean

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Fatty acid metabolism

Pathological process

Warburg effect

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140.0 - 142.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	224.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.95 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.9	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	317.62 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	143 m³·mol⁻¹	ChemAxon
Polarizability	57.65 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	231.937	32859911
AllCCS	[M-H]-	223.945	32859911
DeepCCS	[M+H]+	211.374	30932474
DeepCCS	[M-H]-	209.549	30932474
DeepCCS	[M-2H]-	243.417	30932474
DeepCCS	[M+Na]+	217.193	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
NADH	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	5351.5	Standard polar	33892256
NADH	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	3535.4	Standard non polar	33892256
NADH	NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	5949.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-1301902000-1a1639ad87019605438c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADH GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00n0-0210192000-bf07b6b154c5778067ce	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0150291000-84ef746651797f0679a5	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-0970000000-0688003193d7fc461235	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH LC-ESI-ITFT 35V, negative-QTOF	splash10-00di-0190000000-775fe0fdd09a45ed6a96	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH LC-ESI-ITFT 35V, negative-QTOF	splash10-052b-0019600000-3247f3ea96ec22c0e190	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH LC-ESI-ITFT 35V, negative-QTOF	splash10-052b-0019600000-c62f2c56a1ce8a2874fb	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH LC-ESI-QTOF 32V, negative-QTOF	splash10-03di-3212549000-5bb7a136d3e7ca7d8edd	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH LC-ESI-QTOF 30V, negative-QTOF	splash10-00ea-1219600000-1e722b38e19c9839c336	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 30V, Positive-QTOF	splash10-00ea-1219600000-25943c109cf639eb967c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 30V, Positive-QTOF	splash10-05dj-5449401000-5b1b9b660a66672f95af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 20V, Negative-QTOF	splash10-03di-0000009000-c3a8f40f5761a0b33639	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 40V, Negative-QTOF	splash10-054k-6339301000-c1dfbc12dc893f53f0a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 10V, Negative-QTOF	splash10-03di-0000009000-ced4da70fe9076bb4c29	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 30V, Negative-QTOF	splash10-05dj-5449401000-1c9466169a2e22067bd9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 10V, Positive-QTOF	splash10-00kb-0000009000-f46730c3cbc0e239c819	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 40V, Positive-QTOF	splash10-0udi-1329230000-4e5a5ac7f7ccdfcf5798	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 30V, Negative-QTOF	splash10-00ea-1219600000-1e722b38e19c9839c336	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADH 20V, Positive-QTOF	splash10-0002-0002049000-452a7a02c7cdd0a7db02	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 10V, Positive-QTOF	splash10-000i-0931104000-bf6579d19ee9bc297e13	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 20V, Positive-QTOF	splash10-000i-0901000000-92672b1d4b96838f8652	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 40V, Positive-QTOF	splash10-000i-1900000000-ef56d203da65089e145f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 10V, Negative-QTOF	splash10-03e9-1900207000-f248eb28a7283de7118b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 20V, Negative-QTOF	splash10-001i-1900100000-efadf1d6c54e9e86671d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 40V, Negative-QTOF	splash10-0a7i-3900000000-f258fc2bf1d8e54ac6da	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADH 10V, Negative-QTOF	splash10-03di-0000009000-7483a50cefc91ed6c523	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2018-05-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Mitochondria
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood

Tissue Locations

Bladder
Brain
Fibroblasts
Platelet
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Histidine metabolism
Malate-Aspartate Shuttle		Not Available
Glycerolipid Metabolism
Nitrogen metabolism	Not Available
Glycolysis

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	22.0 (14.0-40.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0081 uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	28792876	details

Associated Disorders and Diseases

Disease References

Nicotinamide Adenine Dinucleotide Deficiency

Shi H, Enriquez A, Rapadas M, Martin EMMA, Wang R, Moreau J, Lim CK, Szot JO, Ip E, Hughes JN, Sugimoto K, Humphreys DT, McInerney-Leo AM, Leo PJ, Maghzal GJ, Halliday J, Smith J, Colley A, Mark PR, Collins F, Sillence DO, Winlaw DS, Ho JWK, Guillemin GJ, Brown MA, Kikuchi K, Thomas PQ, Stocker R, Giannoulatou E, Chapman G, Duncan EL, Sparrow DB, Dunwoodie SL: NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552. doi: 10.1056/NEJMoa1616361. [PubMed:28792876 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB00157

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Nicotinamide_adenine_dinucleotide

METLIN ID

3687

PubChem Compound

439153

PDB ID

Not Available

ChEBI ID

16908

Food Biomarker Ontology

Not Available

VMH ID

HC02112

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Marek, Miroslav; Vrbova, Eva; Horakova, Irena; Musil, Petr; Kefurt, Karel. NADH manufacture with immobilized Candida formate dehydrogenase. Czech. (1992), 4 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Krotz F, Sohn HY, Gloe T, Zahler S, Riexinger T, Schiele TM, Becker BF, Theisen K, Klauss V, Pohl U: NAD(P)H oxidase-dependent platelet superoxide anion release increases platelet recruitment. Blood. 2002 Aug 1;100(3):917-24. [PubMed:12130503 ]
Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Ethanol as a xanthine dehydrogenase inhibitor. Metabolism. 1995 Jun;44(6):779-85. [PubMed:7783663 ]
Nadlinger K, Westerthaler W, Storga-Tomic D, Birkmayer JG: Extracellular metabolisation of NADH by blood cells correlates with intracellular ATP levels. Biochim Biophys Acta. 2002 Nov 14;1573(2):177-82. [PubMed:12399028 ]
Saada A, Bar-Meir M, Belaiche C, Miller C, Elpeleg O: Evaluation of enzymatic assays and compounds affecting ATP production in mitochondrial respiratory chain complex I deficiency. Anal Biochem. 2004 Dec 1;335(1):66-72. [PubMed:15519572 ]
Heiman-Patterson TD, Argov Z, Chavin JM, Kalman B, Alder H, DiMauro S, Bank W, Tahmoush AJ: Biochemical and genetic studies in a family with mitochondrial myopathy. Muscle Nerve. 1997 Oct;20(10):1219-24. [PubMed:9324076 ]
Mintun MA, Vlassenko AG, Rundle MM, Raichle ME: Increased lactate/pyruvate ratio augments blood flow in physiologically activated human brain. Proc Natl Acad Sci U S A. 2004 Jan 13;101(2):659-64. Epub 2004 Jan 2. [PubMed:14704276 ]
Yeo SF, Zhang Y, Schafer D, Campbell S, Wong B: A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum. J Clin Microbiol. 2000 Apr;38(4):1439-43. [PubMed:10747122 ]
Uppal A, Ghosh N, Datta A, Gupta PK: Fluorimetric estimation of the concentration of NADH from human blood samples. Biotechnol Appl Biochem. 2005 Feb;41(Pt 1):43-7. [PubMed:15035655 ]
Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Xylitol-induced increase in the concentration of oxypurines and its mechanism. Int J Clin Pharmacol Ther. 1995 Jun;33(6):360-5. [PubMed:7582389 ]
Helge JW, Fraser AM, Kriketos AD, Jenkins AB, Calvert GD, Ayre KJ, Storlien LH: Interrelationships between muscle fibre type, substrate oxidation and body fat. Int J Obes Relat Metab Disord. 1999 Sep;23(9):986-91. [PubMed:10490806 ]
Fulco M, Schiltz RL, Iezzi S, King MT, Zhao P, Kashiwaya Y, Hoffman E, Veech RL, Sartorelli V: Sir2 regulates skeletal muscle differentiation as a potential sensor of the redox state. Mol Cell. 2003 Jul;12(1):51-62. [PubMed:12887892 ]
Li D, Gan Y, Wientjes MG, Badalament RA, Au JL: Distribution of DT-diaphorase and reduced nicotinamide adenine dinucleotide phosphate: cytochrome p450 oxidoreductase in bladder tissues and tumors. J Urol. 2001 Dec;166(6):2500-5. [PubMed:11696818 ]
Desir G, Bratusch-Marrain P, DeFronzo RA: Effect of hyperketonemia on renal ammonia excretion in man. Metabolism. 1986 Aug;35(8):736-43. [PubMed:3736414 ]
Odland LM, Heigenhauser GJ, Spriet LL: Effects of high fat provision on muscle PDH activation and malonyl-CoA content in moderate exercise. J Appl Physiol (1985). 2000 Dec;89(6):2352-8. [PubMed:11090589 ]
Rani K, Garg P, Pundir CS: Measurement of bile acid in serum and bile with arylamine-glass-bound 3alpha-hydroxysteroid dehydrogenase and diaphorase. Anal Biochem. 2004 Sep 1;332(1):32-7. [PubMed:15301946 ]
Nomura H, Koike F, Tsuruta Y, Iwaki A, Iwaki T: Autopsy case of autosomal recessive hereditary spastic paraplegia with reference to the muscular pathology. Neuropathology. 2001 Sep;21(3):212-7. [PubMed:11666018 ]
Orallo F, Alvarez E, Camina M, Leiro JM, Gomez E, Fernandez P: The possible implication of trans-Resveratrol in the cardioprotective effects of long-term moderate wine consumption. Mol Pharmacol. 2002 Feb;61(2):294-302. [PubMed:11809853 ]
Jawed S, Stevens CR, Harrison R, Blake DR: Elevated circulating plasma NADH oxidising activity of xanthine oxidoreductase in plasma. Biochem Soc Trans. 1997 Aug;25(3):531S. [PubMed:9388747 ]
Harbord MG, Hwang PA, Robinson BH, Becker LE, Hunjan A, Murphy EG: Infant-onset progressive myoclonus epilepsy. J Child Neurol. 1991 Apr;6(2):134-42. [PubMed:1904460 ]
Mayevsky A, Meilin S, Manor T, Ornstein E, Zarchin N, Sonn J: Multiparametric monitoring of brain oxygen balance under experimental and clinical conditions. Neurol Res. 1998;20 Suppl 1:S76-80. [PubMed:9584930 ]
Biellmann JF, Lapinte C, Haid E, Weimann G: Structure of lactate dehydrogenase inhibitor generated from coenzyme. Biochemistry. 1979 Apr 3;18(7):1212-7. [PubMed:218616 ]
Lin SJ, Guarente L: Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease. Curr Opin Cell Biol. 2003 Apr;15(2):241-6. [PubMed:12648681 ]
Belenky P, Bogan KL, Brenner C: NAD+ metabolism in health and disease. Trends Biochem Sci. 2007 Jan;32(1):12-9. Epub 2006 Dec 11. [PubMed:17161604 ]
Pollak N, Dolle C, Ziegler M: The power to reduce: pyridine nucleotides--small molecules with a multitude of functions. Biochem J. 2007 Mar 1;402(2):205-18. [PubMed:17295611 ]
Khan JA, Forouhar F, Tao X, Tong L: Nicotinamide adenine dinucleotide metabolism as an attractive target for drug discovery. Expert Opin Ther Targets. 2007 May;11(5):695-705. [PubMed:17465726 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
WholeHealthMD [Link]

Only showing the first 10 proteins. There are 219 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHB
Uniprot ID:: P11177
Molecular weight:: 39233.1

Enzyme Details

2. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA1
Uniprot ID:: P08559
Molecular weight:: 43295.255

Reactions

Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoA	details

Enzyme Details

3. Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA2
Uniprot ID:: P29803
Molecular weight:: 42932.855

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Reactions

2-Methyl-3-oxopropanoic acid + Coenzyme A + Water + NAD → Propionyl-CoA + Hydrogen carbonate + NADH	details
Malonic semialdehyde + Coenzyme A + NAD → Acetyl-CoA + Carbon dioxide + NADH + Hydrogen Ion	details
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD → Propionyl-CoA + Carbon dioxide + NADH + Hydrogen Ion	details
(S)-Methylmalonic acid semialdehyde + Coenzyme A + NAD → Methylmalonyl-CoA + NADH + Hydrogen Ion	details

Enzyme Details

5. Dihydrolipoyl dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:: DLD
Uniprot ID:: P09622
Molecular weight:: 54176.91

Reactions

Protein N(6)-(dihydrolipoyl)lysine + NAD → protein N(6)-(lipoyl)lysine + NADH	details
Dihydrolipoamide + NAD → Lipoamide + NADH + Hydrogen Ion	details
Dihydrolipoylprotein + NAD → Lipoylprotein + NADH + Hydrogen Ion	details
Enzyme N6-(dihydrolipoyl)lysine + NAD → Enzyme N6-(lipoyl)lysine + NADH + Hydrogen Ion	details
Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoA	details

Enzyme Details

6. Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: DLAT
Uniprot ID:: P10515
Molecular weight:: 68996.03

Reactions

Coenzyme A + NAD + Pyruvic acid → Carbon dioxide + Hydrogen Ion + NADH + Acetyl-CoA	details

Enzyme Details

7. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

Androsterone + NAD → Androstanedione + NADH + Hydrogen Ion	details
Etiocholanolone + NAD → Etiocholanedione + NADH + Hydrogen Ion	details
3a,7a-Dihydroxy-5b-cholestane + NAD → 7a-Hydroxy-5b-cholestan-3-one + NADH + Hydrogen Ion	details
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Ion	details
Tetrahydrocortisone + NAD → 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Ion	details
Tetrahydrocortisol + NAD → Dihydrocortisol + NADH + Hydrogen Ion	details
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NAD → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADH + Hydrogen Ion	details
Tetrahydrocorticosterone + NAD → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADH + Hydrogen Ion	details
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Ion	details
3a-Hydroxy-5b-pregnane-20-one + NAD → 5a-Pregnane-3,20-dione + NADH + Hydrogen Ion	details

Enzyme Details

8. 15-hydroxyprostaglandin dehydrogenase [NAD(+)]

General function:: Involved in oxidoreductase activity
Specific function:: Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipoxin A4. Inhibits in vivo proliferation of colon cancer cells.
Gene Name:: HPGD
Uniprot ID:: P15428
Molecular weight:: 28977.105

Reactions

(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate + NAD → (5Z,13E)-11-alpha-hydroxy-9,15-dioxoprost-5,13-dienoate + NADH	details

Enzyme Details

9. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Reactions

Tyramine + Oxygen + NADH + Hydrogen Ion → Dopamine + NAD + Water	details

Enzyme Details

10. Aldose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:: AKR1B1
Uniprot ID:: P15121
Molecular weight:: 35853.125

Reactions

Glycerol + NAD → Glyceraldehyde + NADH + Hydrogen Ion	details
beta-D-Galactose + NADH + Hydrogen Ion → Galactitol + NAD	details
L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Ion	details
Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Ion	details

Only showing the first 10 proteins. There are 219 proteins in total.

Show all enzymes and transporters

Showing metabocard for NADH (HMDB0001487)

MOL for HMDB0001487 (NADH)

3D MOL for HMDB0001487 (NADH)

3D SDF for HMDB0001487 (NADH)

3D-SDF for HMDB0001487 (NADH)

PDB for HMDB0001487 (NADH)

3D PDB for HMDB0001487 (NADH)

SMILES for HMDB0001487 (NADH)

INCHI for HMDB0001487 (NADH)

Structure for HMDB0001487 (NADH)

3D Structure for HMDB0001487 (NADH)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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