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

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 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


  Mrv1652311221917342D          

 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

$$$$

https://cactus.nci.nih.gov/chemical/structure/NC(=O)C1=CN(C=CC1)%5BC@@H%5D1O%...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:72})
 73 77  0  0  0  0  0  0  0  0999 V2000
    6.9828    5.9021    1.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8592    5.0172    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8391    5.4077   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7529    3.6349    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6301    2.7632   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5350    1.4219   -0.1460 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211    0.9105    1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0484    1.6943    2.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7856    3.1691    2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0247    0.5231   -1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6758    1.0962   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9575   -0.2967   -0.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774   -1.4318   -1.5488 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3531   -1.1600   -2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708   -2.6002   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037   -2.2577   -0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -3.2556    0.0897 P   0  0  1  0  0  0  0  0  0  0  0  0
    1.5321   -4.5483   -0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -3.6815    1.4000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -2.4976    0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081   -2.7426    1.2741 P   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7695   -3.9870    0.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -3.0381    2.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4219    1.2984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.2859    2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141    0.0844    1.9177 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8699    0.8691    2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1613    0.1544    0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    0.9720    0.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0853    2.0290    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0097    0.5269    1.9960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5777   -0.3933    1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407    1.5625    2.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    0.2884    2.9076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9203   -0.6042    3.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
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 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 73  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 22-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-NOV-19         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    https://cactus.nci.nih.gov/chemical/structure/NC(=O)C1=CN(C=CC1)%5BC@@H%5D1O%... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
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HETATM    2  C   UNL     1       6.859   5.017   0.347  1.00  0.00           C  
HETATM    3  O   UNL     1       6.839   5.408  -0.807  1.00  0.00           O  
HETATM    4  C   UNL     1       6.753   3.635   0.627  1.00  0.00           C  
HETATM    5  C   UNL     1       6.630   2.763  -0.390  1.00  0.00           C  
HETATM    6  N   UNL     1       6.535   1.422  -0.146  1.00  0.00           N  
HETATM    7  C   UNL     1       6.921   0.910   1.086  1.00  0.00           C  
HETATM    8  C   UNL     1       7.048   1.694   2.133  1.00  0.00           C  
HETATM    9  C   UNL     1       6.786   3.169   2.055  1.00  0.00           C  
HETATM   10  C   UNL     1       6.025   0.523  -1.184  1.00  0.00           C  
HETATM   11  H   UNL     1       5.676   1.096  -2.043  1.00  0.00           H  
HETATM   12  O   UNL     1       4.957  -0.297  -0.660  1.00  0.00           O  
HETATM   13  C   UNL     1       4.877  -1.432  -1.549  1.00  0.00           C  
HETATM   14  H   UNL     1       4.353  -1.160  -2.465  1.00  0.00           H  
HETATM   15  C   UNL     1       4.171  -2.600  -0.859  1.00  0.00           C  
HETATM   16  O   UNL     1       2.804  -2.258  -0.623  1.00  0.00           O  
HETATM   17  P   UNL     1       1.760  -3.256   0.090  1.00  0.00           P  
HETATM   18  O   UNL     1       1.532  -4.548  -0.843  1.00  0.00           O  
HETATM   19  O   UNL     1       2.300  -3.682   1.400  1.00  0.00           O  
HETATM   20  O   UNL     1       0.357  -2.498   0.309  1.00  0.00           O  
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HETATM   22  O   UNL     1      -1.770  -3.987   0.725  1.00  0.00           O  
HETATM   23  O   UNL     1      -0.433  -3.038   2.644  1.00  0.00           O  
HETATM   24  O   UNL     1      -1.829  -1.422   1.298  1.00  0.00           O  
HETATM   25  C   UNL     1      -2.972  -1.286   2.144  1.00  0.00           C  
HETATM   26  C   UNL     1      -3.614   0.084   1.918  1.00  0.00           C  
HETATM   27  H   UNL     1      -2.870   0.869   2.054  1.00  0.00           H  
HETATM   28  O   UNL     1      -4.161   0.154   0.590  1.00  0.00           O  
HETATM   29  C   UNL     1      -5.349   0.972   0.666  1.00  0.00           C  
HETATM   30  H   UNL     1      -5.085   2.029   0.704  1.00  0.00           H  
HETATM   31  C   UNL     1      -6.010   0.527   1.996  1.00  0.00           C  
HETATM   32  H   UNL     1      -6.578  -0.393   1.859  1.00  0.00           H  
HETATM   33  O   UNL     1      -6.841   1.562   2.524  1.00  0.00           O  
HETATM   34  C   UNL     1      -4.777   0.288   2.908  1.00  0.00           C  
HETATM   35  H   UNL     1      -4.920  -0.604   3.517  1.00  0.00           H  
HETATM   36  O   UNL     1      -4.542   1.427   3.739  1.00  0.00           O  
HETATM   37  N   UNL     1      -6.234   0.703  -0.469  1.00  0.00           N  
HETATM   38  C   UNL     1      -6.267  -0.439  -1.213  1.00  0.00           C  
HETATM   39  N   UNL     1      -7.174  -0.339  -2.141  1.00  0.00           N  
HETATM   40  C   UNL     1      -7.778   0.871  -2.052  1.00  0.00           C  
HETATM   41  C   UNL     1      -7.187   1.551  -0.975  1.00  0.00           C  
HETATM   42  N   UNL     1      -7.608   2.775  -0.674  1.00  0.00           N  
HETATM   43  C   UNL     1      -8.567   3.345  -1.373  1.00  0.00           C  
HETATM   44  N   UNL     1      -9.152   2.746  -2.394  1.00  0.00           N  
HETATM   45  C   UNL     1      -8.800   1.520  -2.766  1.00  0.00           C  
HETATM   46  N   UNL     1      -9.420   0.899  -3.837  1.00  0.00           N  
HETATM   47  C   UNL     1       6.347  -1.796  -1.858  1.00  0.00           C  
HETATM   48  H   UNL     1       6.697  -2.576  -1.182  1.00  0.00           H  
HETATM   49  O   UNL     1       6.484  -2.214  -3.217  1.00  0.00           O  
HETATM   50  C   UNL     1       7.120  -0.478  -1.615  1.00  0.00           C  
HETATM   51  H   UNL     1       7.852  -0.607  -0.818  1.00  0.00           H  
HETATM   52  O   UNL     1       7.760  -0.044  -2.816  1.00  0.00           O  
HETATM   53  H   UNL     1       7.056   6.850   1.163  1.00  0.00           H  
HETATM   54  H   UNL     1       6.995   5.591   2.274  1.00  0.00           H  
HETATM   55  H   UNL     1       6.606   3.126  -1.407  1.00  0.00           H  
HETATM   56  H   UNL     1       7.120  -0.146   1.185  1.00  0.00           H  
HETATM   57  H   UNL     1       7.354   1.265   3.076  1.00  0.00           H  
HETATM   58  H   UNL     1       7.569   3.702   2.594  1.00  0.00           H  
HETATM   59  H   UNL     1       5.823   3.386   2.517  1.00  0.00           H  
HETATM   60  H   UNL     1       4.219  -3.482  -1.497  1.00  0.00           H  
HETATM   61  H   UNL     1       4.662  -2.812   0.091  1.00  0.00           H  
HETATM   62  H   UNL     1       1.179  -4.344  -1.719  1.00  0.00           H  
HETATM   63  H   UNL     1      -2.114  -3.863  -0.170  1.00  0.00           H  
HETATM   64  H   UNL     1      -3.694  -2.068   1.909  1.00  0.00           H  
HETATM   65  H   UNL     1      -2.666  -1.376   3.187  1.00  0.00           H  
HETATM   66  H   UNL     1      -7.276   1.331   3.356  1.00  0.00           H  
HETATM   67  H   UNL     1      -5.271   1.633   4.339  1.00  0.00           H  
HETATM   68  H   UNL     1      -5.635  -1.300  -1.056  1.00  0.00           H  
HETATM   69  H   UNL     1      -8.886   4.341  -1.102  1.00  0.00           H  
HETATM   70  H   UNL     1     -10.120   1.360  -4.326  1.00  0.00           H  
HETATM   71  H   UNL     1      -9.154   0.004  -4.099  1.00  0.00           H  
HETATM   72  H   UNL     1       7.387  -2.454  -3.466  1.00  0.00           H  
HETATM   73  H   UNL     1       8.414  -0.667  -3.160  1.00  0.00           H  
CONECT    1    2   53   54                                            
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5    5    9                                       
CONECT    5    4    4    6   55                                       
CONECT    6    5    7   10                                            
CONECT    7    6    8    8   56                                       
CONECT    8    7    7    9   57                                       
CONECT    9    8    4   58   59                                       
CONECT   10    6   11   12   50                                       
CONECT   11   10                                                      
CONECT   12   10   13                                                 
CONECT   13   12   14   15   47                                       
CONECT   14   13                                                      
CONECT   15   13   16   60   61                                       
CONECT   16   15   17                                                 
CONECT   17   16   18   19   19                                       
CONECT   17   20                                                      
CONECT   18   17   62                                                 
CONECT   19   17   17                                                 
CONECT   20   17   21                                                 
CONECT   21   20   22   23   23                                       
CONECT   21   24                                                      
CONECT   22   21   63                                                 
CONECT   23   21   21                                                 
CONECT   24   21   25                                                 
CONECT   25   24   26   64   65                                       
CONECT   26   25   27   28   34                                       
CONECT   27   26                                                      
CONECT   28   26   29                                                 
CONECT   29   28   30   31   37                                       
CONECT   30   29                                                      
CONECT   31   29   32   33   34                                       
CONECT   32   31                                                      
CONECT   33   31   66                                                 
CONECT   34   31   35   26   36                                       
CONECT   35   34                                                      
CONECT   36   34   67                                                 
CONECT   37   29   38   41                                            
CONECT   38   37   39   39   68                                       
CONECT   39   38   38   40                                            
CONECT   40   39   41   41   45                                       
CONECT   41   40   40   37   42                                       
CONECT   42   41   43   43                                            
CONECT   43   42   42   44   69                                       
CONECT   44   43   45   45                                            
CONECT   45   44   44   40   46                                       
CONECT   46   45   70   71                                            
CONECT   47   13   48   49   50                                       
CONECT   48   47                                                      
CONECT   49   47   72                                                 
CONECT   50   47   51   10   52                                       
CONECT   51   50                                                      
CONECT   52   50   73                                                 
CONECT   53    1                                                      
CONECT   54    1                                                      
CONECT   55    5                                                      
CONECT   56    7                                                      
CONECT   57    8                                                      
CONECT   58    9                                                      
CONECT   59    9                                                      
CONECT   60   15                                                      
CONECT   61   15                                                      
CONECT   62   18                                                      
CONECT   63   22                                                      
CONECT   64   25                                                      
CONECT   65   25                                                      
CONECT   66   33                                                      
CONECT   67   36                                                      
CONECT   68   38                                                      
CONECT   69   43                                                      
CONECT   70   46                                                      
CONECT   71   46                                                      
CONECT   72   49                                                      
CONECT   73   52                                                      
MASTER        0    0    0    0    0    0    0    0   73    0   73    0
END

https://cactus.nci.nih.gov/chemical/structure/NC(=O)C1=CN(C=CC1)%5BC@@H%5D1O%...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:72})
 73 77  0  0  0  0  0  0  0  0999 V2000
    6.9828    5.9021    1.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8592    5.0172    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8391    5.4077   -0.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7529    3.6349    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6301    2.7632   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5350    1.4219   -0.1460 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9211    0.9105    1.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0484    1.6943    2.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7856    3.1691    2.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0247    0.5231   -1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6758    1.0962   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9575   -0.2967   -0.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8774   -1.4318   -1.5488 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3531   -1.1600   -2.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1708   -2.6002   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037   -2.2577   -0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601   -3.2556    0.0897 P   0  0  1  0  0  0  0  0  0  0  0  0
    1.5321   -4.5483   -0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -3.6815    1.4000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3567   -2.4976    0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9081   -2.7426    1.2741 P   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7695   -3.9870    0.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -3.0381    2.6443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.4219    1.2984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.2859    2.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141    0.0844    1.9177 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8699    0.8691    2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1613    0.1544    0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    0.9720    0.6665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0853    2.0290    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0097    0.5269    1.9960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5777   -0.3933    1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8407    1.5625    2.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    0.2884    2.9076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9203   -0.6042    3.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5420    1.4270    3.7385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2344    0.7027   -0.4691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674   -0.4391   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1739   -0.3387   -2.1414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7784    0.8706   -2.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1867    1.5509   -0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6083    2.7750   -0.6741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5666    3.3452   -1.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1525    2.7456   -2.3938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8003    1.5196   -2.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4198    0.8995   -3.8372 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3466   -1.7956   -1.8578 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6971   -2.5758   -1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836   -2.2137   -3.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1197   -0.4781   -1.6146 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8522   -0.6066   -0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7597   -0.0439   -2.8162 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0557    6.8500    1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9948    5.5914    2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061    3.1260   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195   -0.1465    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3545    1.2653    3.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    3.7017    2.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226    3.3864    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193   -3.4824   -1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6617   -2.8116    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -4.3437   -1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -3.8627   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -2.0683    1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6662   -1.3758    3.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2764    1.3314    3.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2711    1.6329    4.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6345   -1.2999   -1.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8860    4.3407   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1199    1.3601   -4.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1538    0.0043   -4.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3867   -2.4542   -3.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4144   -0.6669   -3.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 53  1  0  0  0  0
  1 54  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 55  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7 56  1  0  0  0  0
  8  9  1  0  0  0  0
  8 57  1  0  0  0  0
  9 58  1  0  0  0  0
  9 59  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 10 50  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 13 47  1  0  0  0  0
 15 16  1  0  0  0  0
 15 60  1  0  0  0  0
 15 61  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  1  0  0  0
 17 20  1  0  0  0  0
 18 62  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  1  0  0  0
 21 24  1  0  0  0  0
 22 63  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 26 34  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 29 37  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 33 66  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 67  1  0  0  0  0
 37 38  1  0  0  0  0
 37 41  1  0  0  0  0
 38 39  2  0  0  0  0
 38 68  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 45  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 69  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 70  1  0  0  0  0
 46 71  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 47 50  1  0  0  0  0
 49 72  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 73  1  0  0  0  0
M  END
$$$$

View in JSmol 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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Muscle

Organ and components:

Cell and elements:

Element:

Platelet

Cell:

Fibroblast

Biofluid and excreta:

Blood

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Biochemical process:

Fatty acid metabolism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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

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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M-H]-	Experimental	Astarita_neg	224.3	30932474
DarkChem	[M+H]+	Predicted	Not Available		31661259
DarkChem	[M-H]-	Predicted	Not Available		31661259
AllCCS	[M+H]+	Predicted	Not Available	231.937	32859911
AllCCS	[M-H]-	Predicted	Not Available	223.945	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-1301902000-1a1639ad87019605438c	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002b-1301902000-1a1639ad87019605438c	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00n0-0210192000-bf07b6b154c5778067ce	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0150291000-84ef746651797f0679a5	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0970000000-0688003193d7fc461235	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-00di-0190000000-775fe0fdd09a45ed6a96	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-052b-0019600000-3247f3ea96ec22c0e190	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative	splash10-052b-0019600000-c62f2c56a1ce8a2874fb	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-03di-3212549000-5bb7a136d3e7ca7d8edd	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-00ea-1219600000-1e722b38e19c9839c336	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0931104000-bf6579d19ee9bc297e13	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-92672b1d4b96838f8652	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-ef56d203da65089e145f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-1900207000-f248eb28a7283de7118b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900100000-efadf1d6c54e9e86671d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-3900000000-f258fc2bf1d8e54ac6da	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000009000-7483a50cefc91ed6c523	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-8300019000-ff2563ac55ede9fc0f69	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6s-4539513000-6750c13a8d6fe643a5eb	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0200019000-83faade2f285d81f1520	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-0833149000-ab3d358d7d6c8e3a9c4e	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000j-1923200000-b013fe21d9ec536d8c04	2021-09-07	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2018-05-25	View Spectrum
2D NMR	[¹H, ¹H] 2D NMR Spectrum (predicted)	2018-05-25	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, H₂O, predicted)	2018-05-25	View Spectrum

Biological Properties

Cellular Locations

Mitochondria
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood

Tissue Locations

Bladder
Brain
Fibroblasts
Platelet
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Histidine Metabolism
Malate-Aspartate Shuttle		Not Available
Glycerolipid Metabolism
Ammonia Recycling
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

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

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 ]
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 ]
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)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

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