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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (207) Show 207 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

HMDB0000217

Secondary Accession Numbers

HMDB00217

Metabolite Identification

Common Name

NADP

Description

Nicotinamide adenine dinucleotide phosphate (NADP) is a coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled with a pyrophosphate linkage to 5'-phosphate adenosine 2',5'-bisphosphate. NADP serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). NADP is formed through the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage (Dorland, 27th ed). This extra phosphate is added by the enzyme NAD+ kinase and removed via NADP+ phosphatase. NADP is also known as TPN (triphosphopyridine nucleotide) and it is an important cofactor used in anabolic reactions in all forms of cellular life. Examples include the Calvin cycle, cholesterol synthesis, fatty acid elongation, and nucleic acid synthesis (Wikipedia ).

Structure

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


  Mrv1652309032023572D          

 48 52  0  0  0  0            999 V2000
 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  5  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  3  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
 9996.7195 9997.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8990 9997.2936    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8141 9996.4731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5614 9998.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1466 9996.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  2  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  2  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26  2  1  6  0  0  0
 25  1  1  1  0  0  0
 19  8  1  1  0  0  0
 21 10  1  6  0  0  0
 20  9  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 31 32  2  0  0  0  0
 32 27  1  0  0  0  0
 32 11  1  0  0  0  0
 37 38  2  0  0  0  0
 38 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 33 39  1  0  0  0  0
 41 42  2  0  0  0  0
 38 42  1  0  0  0  0
 40 41  1  0  0  0  0
 37 40  1  0  0  0  0
 43 40  1  6  0  0  0
 43 24  1  0  0  0  0
 23 43  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 22 30  1  1  0  0  0
  6 15  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 24 47  1  1  0  0  0
M  CHG  2  15  -1  30   1
M  END

HMDB0000217
     RDKit          3D
NADP
 76 80  0  0  0  0  0  0  0  0999 V2000
  -10.2455   -1.7030   -2.9146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2839   -2.2860   -2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9879   -3.5100   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6727   -1.5682   -0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9324   -1.9821    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2938   -1.3622    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4033   -0.3311    1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1324    0.0943   -0.1464 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.3119    1.2052   -0.4753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9590    1.1534   -0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639    1.5806    0.9610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8198    0.4759    1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100    0.7739    0.9305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986   -0.4033   -0.0450 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6913   -1.6542   -0.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.3346   -1.6820 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.2583   -0.6934    0.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140   -0.8708   -1.5508 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.0688    0.2721   -2.4268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947   -2.2918   -2.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034   -1.0584   -1.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489   -1.1406   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -1.3057   -0.1926 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770   -0.2776   -0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668   -0.3507   -0.1446 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2631    0.8162    0.5840 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343    1.6179    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    2.7381    1.6913 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2334    2.6872    1.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2758    3.5863    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1233    4.7881    2.3674 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4955    3.2366    1.1540 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6932    2.0635    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6536    1.2326    0.2661 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4328    1.4820    0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409   -1.6697    0.5640 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0943   -2.6975   -0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5593   -2.7574   -1.2090 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.3683   -2.0171   -2.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9577   -4.3422   -1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310   -2.0690   -0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.8137    1.0640 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2595   -3.1941    1.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6969    2.3615    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3031    3.7696    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038    2.4745    0.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3848    3.5516   -0.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7869   -0.5491   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0986   -1.3008   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0582   -1.6699   -3.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6756   -2.7774    0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5029   -1.6853    2.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8645    0.1237    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5420    1.4944   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    2.3779    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0673   -0.4936    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500    0.3318    2.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -2.9505   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.1599    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -2.0227    0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -2.1681   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6460   -0.4455   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.3564    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006    4.7797    3.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4347    5.6835    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6786    1.9024    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653   -1.8047    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5112   -4.3728   -2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464   -2.2579    0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -1.3139    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -3.6639    0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2057    2.1967    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6849    3.8393    2.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7270    2.5067    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0900    4.3444   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6205   -0.2469   -2.1898 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 25 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 38 41  1  0
 36 42  1  0
 42 43  1  0
 11 44  1  0
 44 45  1  0
 44 46  1  0
 46 47  1  0
  8 48  2  0
 48  4  1  0
 46  9  1  0
 42 23  1  0
 35 26  1  0
 35 29  1  0
  1 49  1  0
  1 50  1  0
  5 51  1  0
  6 52  1  0
  7 53  1  0
  9 54  1  6
 11 55  1  6
 12 56  1  0
 12 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
 25 62  1  6
 27 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 36 67  1  1
 40 68  1  0
 41 69  1  0
 42 70  1  1
 43 71  1  0
 44 72  1  1
 45 73  1  0
 46 74  1  1
 47 75  1  0
 48 76  1  0
M  CHG  2   8   1  16  -1
M  END


  Mrv1652309032023572D          

 48 52  0  0  0  0            999 V2000
 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  5  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  3  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
 9996.7195 9997.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8990 9997.2936    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8141 9996.4731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5614 9998.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1466 9996.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  2  0  0  0  0
  4 17  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  2  0  0  0  0
  7  8  1  0  0  0  0
 11 12  1  0  0  0  0
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 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 26  2  1  6  0  0  0
 25  1  1  1  0  0  0
 19  8  1  1  0  0  0
 21 10  1  6  0  0  0
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 43 24  1  0  0  0  0
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 29 30  2  0  0  0  0
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 22 30  1  1  0  0  0
  6 15  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 24 47  1  1  0  0  0
M  CHG  2  15  -1  30   1
M  END
> <DATABASE_ID>
HMDB0000217

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
XJLXINKUBYWONI-NNYOXOHSSA-N

> <FORMULA>
C21H28N7O17P3

> <MOLECULAR_WEIGHT>
743.405

> <EXACT_MASS>
743.075452041

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
62.46247757400349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-10.400339179050357

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.880605793929706

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6557887325664353

> <JCHEM_PKA_STRONGEST_BASIC>
4.002014556353763

> <JCHEM_POLAR_SURFACE_AREA>
367.61999999999995

> <JCHEM_REFRACTIVITY>
151.74810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000217
     RDKit          3D
NADP
 76 80  0  0  0  0  0  0  0  0999 V2000
  -10.2455   -1.7030   -2.9146 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9879   -3.5100   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9324   -1.9821    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2938   -1.3622    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4033   -0.3311    1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1324    0.0943   -0.1464 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.3119    1.2052   -0.4753 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.3343    1.6179    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    2.7381    1.6913 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8310   -2.0690   -0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.8137    1.0640 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2595   -3.1941    1.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6969    2.3615    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3031    3.7696    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038    2.4745    0.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3848    3.5516   -0.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7869   -0.5491   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0986   -1.3008   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0582   -1.6699   -3.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6756   -2.7774    0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5029   -1.6853    2.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8645    0.1237    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8129    2.3779    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0673   -0.4936    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500    0.3318    2.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -2.9505   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6460   -0.4455   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.3564    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006    4.7797    3.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4347    5.6835    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6786    1.9024    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653   -1.8047    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5112   -4.3728   -2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464   -2.2579    0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -1.3139    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -3.6639    0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0900    4.3444   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6205   -0.2469   -2.1898 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 25 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 38 41  1  0
 36 42  1  0
 42 43  1  0
 11 44  1  0
 44 45  1  0
 44 46  1  0
 46 47  1  0
  8 48  2  0
 48  4  1  0
 46  9  1  0
 42 23  1  0
 35 26  1  0
 35 29  1  0
  1 49  1  0
  1 50  1  0
  5 51  1  0
  6 52  1  0
  7 53  1  0
  9 54  1  6
 11 55  1  6
 12 56  1  0
 12 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
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 27 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 36 67  1  1
 40 68  1  0
 41 69  1  0
 42 70  1  1
 43 71  1  0
 44 72  1  1
 45 73  1  0
 46 74  1  1
 47 75  1  0
 48 76  1  0
M  CHG  2   8   1  16  -1
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0    8661.7358663.015   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8662.6828666.489   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8664.0198665.717   0.000  0.00  0.00           O+0
HETATM    4  P   UNK     0    8665.3538666.489   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0    8666.6988665.743   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8668.0308666.511   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0    8669.3668665.743   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8670.6948666.511   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8671.5878663.042   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8674.9288663.057   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8679.8678665.766   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8681.2038666.535   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0    8679.8678664.227   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8667.2608667.846   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8668.8008667.846   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0    8664.5818667.823   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8666.1218667.823   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8673.2718666.665   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8672.0258665.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8672.5018664.295   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8674.0418664.295   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8674.5168665.760   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8660.0988666.639   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0    8659.3288664.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8660.8688664.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8661.3438665.734   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8678.5238668.052   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8677.1898668.822   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8675.8568668.052   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8675.8558666.512   0.000  0.00  0.00           N+1
HETATM   31  C   UNK     0    8677.1898665.742   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8678.5238666.512   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8653.6628667.173   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0    8653.0358665.767   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0    8653.9418664.521   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0    8655.4728664.681   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0    8656.0998666.088   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8655.1938667.334   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0    8652.7568668.419   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0    8657.5638666.564   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0    8657.5638668.104   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0    8656.0998668.580   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0    8658.8098665.659   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0    8660.5438661.454   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0    8659.0118661.615   0.000  0.00  0.00           P+0
HETATM   46  O   UNK     0    8658.8538660.083   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0    8658.3818663.029   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0    8657.6078660.988   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2    3   26                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16   17                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   14   15                                             
CONECT    7    6    8                                                       
CONECT    8    7   19                                                       
CONECT    9   20                                                            
CONECT   10   21                                                            
CONECT   11   12   13   32                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    6                                                            
CONECT   16    4                                                            
CONECT   17    4                                                            
CONECT   18   19   22                                                       
CONECT   19   20   18    8                                                  
CONECT   20   19   21    9                                                  
CONECT   21   20   22   10                                                  
CONECT   22   21   18   30                                                  
CONECT   23   26   43                                                       
CONECT   24   25   43   47                                                  
CONECT   25   24   26    1                                                  
CONECT   26   25   23    2                                                  
CONECT   27   28   32                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   22                                                  
CONECT   31   32   30                                                       
CONECT   32   31   27   11                                                  
CONECT   33   38   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   38   36   40                                                  
CONECT   38   37   33   42                                                  
CONECT   39   33                                                            
CONECT   40   41   37   43                                                  
CONECT   41   42   40                                                       
CONECT   42   41   38                                                       
CONECT   43   40   24   23                                                  
CONECT   44   45                                                            
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45   24                                                       
CONECT   48   45                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

COMPND    HMDB0000217
HETATM    1  N1  UNL     1     -10.246  -1.703  -2.915  1.00  0.00           N  
HETATM    2  C1  UNL     1      -9.284  -2.286  -2.053  1.00  0.00           C  
HETATM    3  O1  UNL     1      -8.988  -3.510  -2.296  1.00  0.00           O  
HETATM    4  C2  UNL     1      -8.673  -1.568  -0.977  1.00  0.00           C  
HETATM    5  C3  UNL     1      -8.932  -1.982   0.326  1.00  0.00           C  
HETATM    6  C4  UNL     1      -8.294  -1.362   1.380  1.00  0.00           C  
HETATM    7  C5  UNL     1      -7.403  -0.331   1.094  1.00  0.00           C  
HETATM    8  N2  UNL     1      -7.132   0.094  -0.146  1.00  0.00           N1+
HETATM    9  C6  UNL     1      -6.312   1.205  -0.475  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.959   1.153  -0.413  1.00  0.00           O  
HETATM   11  C7  UNL     1      -4.664   1.581   0.961  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.820   0.476   1.479  1.00  0.00           C  
HETATM   13  O3  UNL     1      -2.510   0.774   0.930  1.00  0.00           O  
HETATM   14  P1  UNL     1      -1.899  -0.403  -0.045  1.00  0.00           P  
HETATM   15  O4  UNL     1      -2.691  -1.654  -0.168  1.00  0.00           O  
HETATM   16  O5  UNL     1      -2.078   0.335  -1.682  1.00  0.00           O1-
HETATM   17  O6  UNL     1      -0.258  -0.693   0.051  1.00  0.00           O  
HETATM   18  P2  UNL     1       0.314  -0.871  -1.551  1.00  0.00           P  
HETATM   19  O7  UNL     1      -0.069   0.272  -2.427  1.00  0.00           O  
HETATM   20  O8  UNL     1      -0.395  -2.292  -2.173  1.00  0.00           O  
HETATM   21  O9  UNL     1       2.003  -1.058  -1.564  1.00  0.00           O  
HETATM   22  C9  UNL     1       2.449  -1.141  -0.202  1.00  0.00           C  
HETATM   23  C10 UNL     1       3.905  -1.306  -0.193  1.00  0.00           C  
HETATM   24  O10 UNL     1       4.677  -0.278  -0.713  1.00  0.00           O  
HETATM   25  C11 UNL     1       5.967  -0.351  -0.145  1.00  0.00           C  
HETATM   26  N3  UNL     1       6.263   0.816   0.584  1.00  0.00           N  
HETATM   27  C12 UNL     1       5.334   1.618   1.201  1.00  0.00           C  
HETATM   28  N4  UNL     1       5.955   2.738   1.691  1.00  0.00           N  
HETATM   29  C13 UNL     1       7.233   2.687   1.391  1.00  0.00           C  
HETATM   30  C14 UNL     1       8.276   3.586   1.634  1.00  0.00           C  
HETATM   31  N5  UNL     1       8.123   4.788   2.367  1.00  0.00           N  
HETATM   32  N6  UNL     1       9.496   3.237   1.154  1.00  0.00           N  
HETATM   33  C15 UNL     1       9.693   2.064   0.469  1.00  0.00           C  
HETATM   34  N7  UNL     1       8.654   1.233   0.266  1.00  0.00           N  
HETATM   35  C16 UNL     1       7.433   1.482   0.696  1.00  0.00           C  
HETATM   36  C17 UNL     1       6.041  -1.670   0.564  1.00  0.00           C  
HETATM   37  O11 UNL     1       6.094  -2.697  -0.457  1.00  0.00           O  
HETATM   38  P3  UNL     1       7.559  -2.757  -1.209  1.00  0.00           P  
HETATM   39  O12 UNL     1       7.368  -2.017  -2.546  1.00  0.00           O  
HETATM   40  O13 UNL     1       7.958  -4.342  -1.656  1.00  0.00           O  
HETATM   41  O14 UNL     1       8.831  -2.069  -0.391  1.00  0.00           O  
HETATM   42  C18 UNL     1       4.584  -1.814   1.064  1.00  0.00           C  
HETATM   43  O15 UNL     1       4.260  -3.194   1.154  1.00  0.00           O  
HETATM   44  C19 UNL     1      -5.697   2.362   1.473  1.00  0.00           C  
HETATM   45  O16 UNL     1      -5.303   3.770   1.622  1.00  0.00           O  
HETATM   46  C20 UNL     1      -6.704   2.474   0.313  1.00  0.00           C  
HETATM   47  O17 UNL     1      -6.385   3.552  -0.505  1.00  0.00           O  
HETATM   48  C21 UNL     1      -7.787  -0.549  -1.171  1.00  0.00           C  
HETATM   49  H1  UNL     1     -11.099  -1.301  -2.510  1.00  0.00           H  
HETATM   50  H2  UNL     1     -10.058  -1.670  -3.909  1.00  0.00           H  
HETATM   51  H3  UNL     1      -9.676  -2.777   0.520  1.00  0.00           H  
HETATM   52  H4  UNL     1      -8.503  -1.685   2.418  1.00  0.00           H  
HETATM   53  H5  UNL     1      -6.865   0.124   1.914  1.00  0.00           H  
HETATM   54  H6  UNL     1      -6.542   1.494  -1.566  1.00  0.00           H  
HETATM   55  H7  UNL     1      -3.813   2.378   0.644  1.00  0.00           H  
HETATM   56  H8  UNL     1      -4.067  -0.494   0.979  1.00  0.00           H  
HETATM   57  H9  UNL     1      -3.750   0.332   2.540  1.00  0.00           H  
HETATM   58  H10 UNL     1      -0.282  -2.950  -1.419  1.00  0.00           H  
HETATM   59  H11 UNL     1       2.112  -0.160   0.212  1.00  0.00           H  
HETATM   60  H12 UNL     1       1.977  -2.023   0.228  1.00  0.00           H  
HETATM   61  H13 UNL     1       4.095  -2.168  -0.973  1.00  0.00           H  
HETATM   62  H14 UNL     1       6.646  -0.446  -1.054  1.00  0.00           H  
HETATM   63  H15 UNL     1       4.284   1.356   1.262  1.00  0.00           H  
HETATM   64  H16 UNL     1       7.701   4.780   3.310  1.00  0.00           H  
HETATM   65  H17 UNL     1       8.435   5.684   1.978  1.00  0.00           H  
HETATM   66  H18 UNL     1      10.679   1.902   0.147  1.00  0.00           H  
HETATM   67  H19 UNL     1       6.765  -1.805   1.293  1.00  0.00           H  
HETATM   68  H20 UNL     1       8.511  -4.373  -2.490  1.00  0.00           H  
HETATM   69  H21 UNL     1       8.746  -2.258   0.583  1.00  0.00           H  
HETATM   70  H22 UNL     1       4.369  -1.314   1.973  1.00  0.00           H  
HETATM   71  H23 UNL     1       4.673  -3.664   0.375  1.00  0.00           H  
HETATM   72  H24 UNL     1      -6.206   2.197   2.435  1.00  0.00           H  
HETATM   73  H25 UNL     1      -4.685   3.839   2.384  1.00  0.00           H  
HETATM   74  H26 UNL     1      -7.727   2.507   0.600  1.00  0.00           H  
HETATM   75  H27 UNL     1      -6.090   4.344  -0.031  1.00  0.00           H  
HETATM   76  H28 UNL     1      -7.620  -0.247  -2.190  1.00  0.00           H  
CONECT    1    2   49   50
CONECT    2    3    3    4
CONECT    4    5    5   48
CONECT    5    6   51
CONECT    6    7    7   52
CONECT    7    8   53
CONECT    8    9   48   48
CONECT    9   10   46   54
CONECT   10   11
CONECT   11   12   44   55
CONECT   12   13   56   57
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   58
CONECT   21   22
CONECT   22   23   59   60
CONECT   23   24   42   61
CONECT   24   25
CONECT   25   26   36   62
CONECT   26   27   35
CONECT   27   28   28   63
CONECT   28   29
CONECT   29   30   30   35
CONECT   30   31   32
CONECT   31   64   65
CONECT   32   33   33
CONECT   33   34   66
CONECT   34   35   35
CONECT   36   37   42   67
CONECT   37   38
CONECT   38   39   39   40   41
CONECT   40   68
CONECT   41   69
CONECT   42   43   70
CONECT   43   71
CONECT   44   45   46   72
CONECT   45   73
CONECT   46   47   74
CONECT   47   75
CONECT   48   76
END

HMDB0000217
     RDKit          3D
NADP
 76 80  0  0  0  0  0  0  0  0999 V2000
  -10.2455   -1.7030   -2.9146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2839   -2.2860   -2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9879   -3.5100   -2.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6727   -1.5682   -0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9324   -1.9821    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2938   -1.3622    1.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4033   -0.3311    1.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1324    0.0943   -0.1464 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.3119    1.2052   -0.4753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9590    1.1534   -0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639    1.5806    0.9610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8198    0.4759    1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100    0.7739    0.9305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986   -0.4033   -0.0450 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6913   -1.6542   -0.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.3346   -1.6820 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.2583   -0.6934    0.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140   -0.8708   -1.5508 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.0688    0.2721   -2.4268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947   -2.2918   -2.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034   -1.0584   -1.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489   -1.1406   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -1.3057   -0.1926 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770   -0.2776   -0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668   -0.3507   -0.1446 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2631    0.8162    0.5840 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343    1.6179    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    2.7381    1.6913 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2334    2.6872    1.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2758    3.5863    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1233    4.7881    2.3674 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4955    3.2366    1.1540 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6932    2.0635    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6536    1.2326    0.2661 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4328    1.4820    0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409   -1.6697    0.5640 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0943   -2.6975   -0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5593   -2.7574   -1.2090 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.3683   -2.0171   -2.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9577   -4.3422   -1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310   -2.0690   -0.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   -1.8137    1.0640 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2595   -3.1941    1.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6969    2.3615    1.4734 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3031    3.7696    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038    2.4745    0.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3848    3.5516   -0.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7869   -0.5491   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0986   -1.3008   -2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0582   -1.6699   -3.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6756   -2.7774    0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5029   -1.6853    2.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8645    0.1237    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5420    1.4944   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    2.3779    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0673   -0.4936    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500    0.3318    2.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -2.9505   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -0.1599    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -2.0227    0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -2.1681   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6460   -0.4455   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.3564    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7006    4.7797    3.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4347    5.6835    1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6786    1.9024    0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653   -1.8047    1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5112   -4.3728   -2.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464   -2.2579    0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694   -1.3139    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -3.6639    0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2057    2.1967    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6849    3.8393    2.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7270    2.5067    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0900    4.3444   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6205   -0.2469   -2.1898 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 25 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 38 41  1  0
 36 42  1  0
 42 43  1  0
 11 44  1  0
 44 45  1  0
 44 46  1  0
 46 47  1  0
  8 48  2  0
 48  4  1  0
 46  9  1  0
 42 23  1  0
 35 26  1  0
 35 29  1  0
  1 49  1  0
  1 50  1  0
  5 51  1  0
  6 52  1  0
  7 53  1  0
  9 54  1  6
 11 55  1  6
 12 56  1  0
 12 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  6
 25 62  1  6
 27 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 36 67  1  1
 40 68  1  0
 41 69  1  0
 42 70  1  1
 43 71  1  0
 44 72  1  1
 45 73  1  0
 46 74  1  1
 47 75  1  0
 48 76  1  0
M  CHG  2   8   1  16  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Codehydrase II	ChEBI
Codehydrogenase II	ChEBI
Coenzyme II	ChEBI
NAD phosphate	ChEBI
NADP nicotinamide-adenine-dinucleotide phosphATE	ChEBI
TPN	ChEBI
Triphosphopyridine nucleotide	ChEBI
NAD phosphoric acid	Generator
NADP nicotinamide-adenine-dinucleotide phosphoric acid	Generator
Dinucleotide phosphate, nicotinamide-adenine	HMDB
NADPH	HMDB
Nicotinamide-adenine dinucleotide phosphate	HMDB
Nicotinamide adenine dinucleotide phosphate	HMDB
Nucleotide, triphosphopyridine	HMDB
Phosphate, nicotinamide-adenine dinucleotide	HMDB
Adenine-nicotinamide dinucleotide phosphate	HMDB
NADP+	HMDB
beta-NADP	HMDB
beta-Nicotinamide adenine dinucleotide phosphate	HMDB
beta-TPN	HMDB
Β-nadp	HMDB
Β-nicotinamide adenine dinucleotide phosphate	HMDB
Β-TPN	HMDB
NADP	ChEBI, MeSH

Chemical Formula

C₂₁H₂₈N₇O₁₇P₃

Average Molecular Weight

743.405

Monoisotopic Molecular Weight

743.075452041

IUPAC Name

1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

Traditional Name

1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

CAS Registry Number

53-59-8

SMILES

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

InChI Identifier

InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

XJLXINKUBYWONI-NNYOXOHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

noradrenaline (CHEBI:18357 )
Biogenic amines (C00547 )
Adrenalines (C00547 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.15 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-10	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	367.62 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	151.75 m³·mol⁻¹	ChemAxon
Polarizability	62.46 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
DeepCCS	[M+H]+	212.5	30932474
DeepCCS	[M-H]-	210.654	30932474
DeepCCS	[M-2H]-	244.686	30932474
DeepCCS	[M+Na]+	218.648	30932474
AllCCS	[M+H]+	237.9	32859911
AllCCS	[M+H-H2O]+	237.6	32859911
AllCCS	[M+NH4]+	238.1	32859911
AllCCS	[M+Na]+	238.1	32859911
AllCCS	[M-H]-	225.4	32859911
AllCCS	[M+Na-2H]-	227.2	32859911
AllCCS	[M+HCOO]-	229.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
NADP	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	5700.9	Standard polar	33892256
NADP	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	3992.4	Standard non polar	33892256
NADP	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O	6237.3	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 - NADP GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NADP GC-MS (TMS_2_18) - 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 - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00dl-0219003700-2f52e3c5db41066a112c	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0uk9-0301009000-a3d0c464e56f6e320c80	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00dl-0000090000-c18a7719161c63a71938	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0udi-0000009000-1dde5b221786fe375304	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-00dl-0209000700-02057593d6470f6a2075	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0uk9-0301109000-bf4996084c09a9176489	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0uk9-0301009000-b3e8d304dfdc4711e0ce	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF	splash10-0udi-0000009000-384d275a638928dd40f1	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00dl-0000229600-bd164bae0cc54f45b961	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-004i-0027900000-25e0180b7638ed18e207	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0011953000-c328377f842fac60b55e	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00di-0000009000-0ec3670e706b086d382a	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00dl-0000109700-df2a731fd5f55e9e7a8e	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-0a4i-0011953000-981d13d6b50f18ebc910	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00di-0000009000-f9526262833104be0a2e	2019-11-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOF	splash10-00di-0000009000-c0cedd489befb2073370	2019-11-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 10V, Positive-QTOF	splash10-0006-0000000900-d510a9264bee14bd85ee	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 20V, Positive-QTOF	splash10-000t-0000000900-fb29571fb864b5c4179b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 40V, Positive-QTOF	splash10-006y-2910001000-5066541857e9b5d8bbbf	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 10V, Negative-QTOF	splash10-0006-1000000900-8cdcef7ab2fa3bdd51e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 20V, Negative-QTOF	splash10-0007-6100000900-396416b5dd4d0892e43d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 40V, Negative-QTOF	splash10-005a-9100000000-e5765145791ae2971a89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 10V, Positive-QTOF	splash10-000i-0900001200-ff4ca74a6b585e359275	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 20V, Positive-QTOF	splash10-000i-0901113400-26884ea59b81b6581275	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NADP 40V, Positive-QTOF	splash10-000j-2902210000-acc59733c27dab4bbf95	2021-09-23	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)	2019-11-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Mitochondria
Nucleus
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood

Tissue Locations

All Tissues

Pathways

Name	SMPDB/PathBank	KEGG
Glucose-Alanine Cycle		Not Available
Nicotinate and nicotinamide metabolism	Not Available
Glutathione metabolism	Not Available
Histidine metabolism
Glycerolipid Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	19.6 (18.3 - 20.8) uM	Adult (>18 years old)	Both	Normal	17709435	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	24.4 (21.5 - 27.4) uM	Adult (>18 years old)	Both	Pellagra	17709435	details

Associated Disorders and Diseases

Disease References

Pellagra
Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB03461

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021908

KNApSAcK ID

Not Available

Chemspider ID

5674

KEGG Compound ID

C00006

BioCyc ID

NADP

BiGG ID

Not Available

Wikipedia Link

Nicotinamide adenine dinucleotide phosphate

METLIN ID

Not Available

PubChem Compound

5885

PDB ID

Not Available

ChEBI ID

44409

Food Biomarker Ontology

Not Available

VMH ID

NADP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Simon, L. M.; Kotorman, M.; Szajani, B. Coenzyme production using immobilized enzymes. I. Preparation, characterization, and laboratory-scale application of an immobilized NAD+ kinase. Enzyme and Microbial Technology (1992), 14(12), 997-1000.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Siddique YH, Beg T, Afzal M: Genotoxic potential of ethinylestradiol in cultured mammalian cells. Chem Biol Interact. 2005 Jan 15;151(2):133-41. [PubMed:15698584 ]
Himmelstein MW, Carpenter SC, Hinderliter PM, Snow TA, Valentine R: The metabolism of beta-chloroprene: preliminary in-vitro studies using liver microsomes. Chem Biol Interact. 2001 Jun 1;135-136:267-84. [PubMed:11397396 ]

Only showing the first 10 proteins. There are 207 proteins in total.

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Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Reactions

(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP → 3-oxoacyl-[acyl-carrier-protein] + NADPH	details
Acyl-[acyl-carrier-protein] + NADP → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPH	details
Butyryl-[acp] + NADP → But-2-enoyl-[acyl-carrier protein] + NADPH + Hydrogen Ion	details
(3R)-3-Hydroxybutanoyl-[acyl-carrier protein] + NADP → Acetoacetyl-[acp] + NADPH + Hydrogen Ion	details
(3R)-3-Hydroxydecanoyl-[acyl-carrier protein] + NADP → 3-Oxodecanoyl-[acp] + NADPH	details
(3R)-3-Hydroxyoctanoyl-[acyl-carrier protein] + NADP → 3-Oxooctanoyl-[acp] + NADPH + Hydrogen Ion	details
(3R)-3-Hydroxypalmitoyl-[acyl-carrier protein] + NADP → 3-Oxohexadecanoyl-[acp] + NADPH + Hydrogen Ion	details
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + NADP → 3-Oxotetradecanoyl-[acp] + NADPH + Hydrogen Ion	details
Dodecanoyl-[acyl-carrier protein] + NADP → trans-Dodec-2-enoyl-[acp] + NADPH + Hydrogen Ion	details
(R)-3-Hydroxyhexanoyl-[acp] + NADP → 3-Oxohexanoyl-[acp] + NADPH + Hydrogen Ion	details
Hexanoyl-[acp] + NADP → trans-Hex-2-enoyl-[acp] + NADPH + Hydrogen Ion	details
Octanoyl-[acp] + NADP → trans-Oct-2-enoyl-[acp] + NADPH + Hydrogen Ion	details
Decanoyl-[acp] + NADP → trans-Dec-2-enoyl-[acp] + NADPH + Hydrogen Ion	details
Tetradecanoyl-[acp] + NADP → trans-Tetradec-2-enoyl-[acp] + NADPH + Hydrogen Ion	details
Hexadecanoyl-[acp] + NADP → trans-Hexadec-2-enoyl-[acp] + NADPH + Hydrogen Ion	details

Enzyme Details

2. 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

Malonic semialdehyde + Coenzyme A + NADP → Acetyl-CoA + Carbon dioxide + NADPH + Hydrogen Ion	details
Malonic semialdehyde + Coenzyme A + NADP → Malonyl-CoA + NADPH + Hydrogen Ion	details

Enzyme Details

3. 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

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

Enzyme Details

4. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

Reactions

R-CHOH-R' + NADP → R-CO-R' + NADPH	details
(5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate + NADP → (5Z,13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH	details
(13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate + NADP → (13E)-11-alpha-hydroxy-9,15-dioxoprost-13-enoate + NADPH	details
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Ion	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP	details

Enzyme Details

5. Dehydrogenase/reductase SDR family member 4

General function:: Involved in oxidoreductase activity
Specific function:: Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:: DHRS4
Uniprot ID:: Q9BTZ2
Molecular weight:: 29536.885

Reactions

R-CHOH-R' + NADP → R-CO-R' + NADPH	details

Enzyme Details

6. Carbonyl reductase [NADPH] 3

General function:: Involved in oxidoreductase activity
Specific function:: Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:: CBR3
Uniprot ID:: O75828
Molecular weight:: 30849.97

Reactions

R-CHOH-R' + NADP → R-CO-R' + NADPH	details
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Ion	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP	details

Enzyme Details

7. 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 + NADP → Glyceraldehyde + NADPH + Hydrogen Ion	details
beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADP	details
D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Ion	details
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Ion	details
Sorbitol + NADP → alpha-D-Glucose + NADPH + Hydrogen Ion	details
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Ion	details

Enzyme Details

8. Thioredoxin reductase 1, cytoplasmic

General function:: Involved in oxidoreductase activity
Specific function:: Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enhances the transcriptional activity of estrogen receptors alpha and beta while isoform 5 enhances the transcriptional activity of the beta receptor only. Isoform 5 also mediates cell death induced by a combination of interferon-beta and retinoic acid.
Gene Name:: TXNRD1
Uniprot ID:: Q16881
Molecular weight:: 70905.58

Reactions

Thioredoxin + NADP → thioredoxin disulfide + NADPH	details
Thioredoxin + NADP → Thioredoxin disulfide + NADPH + Hydrogen Ion	details
Hydrogen selenide + NADP + Water → Selenite + NADPH + Hydrogen Ion	details
NADPH + Hydrogen Ion + Methylselenic acid → NADP + Water + Methaneselenol	details

Enzyme Details

9. Lathosterol oxidase

General function:: Involved in iron ion binding
Specific function:: Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:: SC5DL
Uniprot ID:: O75845
Molecular weight:: 35300.55

Reactions

Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Water	details
Episterol + NADP → 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Ion	details

Enzyme Details

10. Dimethylaniline monooxygenase [N-oxide-forming] 5

General function:: Involved in flavin-containing monooxygenase activity
Specific function:: In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:: FMO5
Uniprot ID:: P49326
Molecular weight:: 32480.04

Reactions

N,N-Dimethylaniline + NADPH + Oxygen → Dimethylaniline-N-oxide + NADP + Water	details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Water	details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Water	details

Only showing the first 10 proteins. There are 207 proteins in total.

Show all enzymes and transporters

Showing metabocard for NADP (HMDB0000217)

MOL for HMDB0000217 (NADP)

3D MOL for HMDB0000217 (NADP)

3D SDF for HMDB0000217 (NADP)

3D-SDF for HMDB0000217 (NADP)

PDB for HMDB0000217 (NADP)

3D PDB for HMDB0000217 (NADP)

SMILES for HMDB0000217 (NADP)

INCHI for HMDB0000217 (NADP)

Structure for HMDB0000217 (NADP)

3D Structure for HMDB0000217 (NADP)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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