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Showing metabocard for NADPH (HMDB0000221)

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enzymes (203) Show 203 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:20 UTC
HMDB IDHMDB0000221
Secondary Accession Numbers
  • HMDB0000799
  • HMDB0006341
  • HMDB00221
  • HMDB00799
  • HMDB06341
Metabolite Identification
Common NameNADPH
DescriptionNADPH is the reduced form of NADP+, and NADP+ is the oxidized form of NADPH. 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
Data?1582752117
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000221 (NADPH)


  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
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10001.4459 9999.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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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
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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
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10003.1253 9998.7296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 22 30  1  1  0  0  0
  6 15  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000221 (NADPH)

HMDB0000221
     RDKit          3D
NADPH
 78 82  0  0  0  0  0  0  0  0999 V2000
   10.1531   -2.1020   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1001   -1.1643   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9539   -0.5546   -1.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1501   -0.8062    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2252    0.0995    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2348    0.5512    1.0736 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.5427    0.6642 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0501    1.1819    0.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
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 46 75  1  0
 47 76  1  0
 48 77  1  0
 48 78  1  0
M  END
Download

3D SDF for HMDB0000221 (NADPH)


  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  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
 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  1  0  0  0  0
 28 29  2  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
 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
 29 30  1  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
M  END
> <DATABASE_ID>
HMDB0000221

> <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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30N7O17P3/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/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
ACFIXJIJDZMPPO-NNYOXOHSSA-N

> <FORMULA>
C21H30N7O17P3

> <MOLECULAR_WEIGHT>
745.4209

> <EXACT_MASS>
745.091102105

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
63.542294008111696

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-6.376368250362743

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8806160343962963

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6557894226872323

> <JCHEM_PKA_STRONGEST_BASIC>
4.00201652313229

> <JCHEM_POLAR_SURFACE_AREA>
364.1500000000001

> <JCHEM_REFRACTIVITY>
153.8726

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nadph

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000221 (NADPH)

HMDB0000221
     RDKit          3D
NADPH
 78 82  0  0  0  0  0  0  0  0999 V2000
   10.1531   -2.1020   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1001   -1.1643   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9539   -0.5546   -1.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1501   -0.8062    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2252    0.0995    0.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2348    0.5512    1.0736 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.5427    0.6642 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0501    1.1819    0.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1785    0.8138   -1.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8065   -0.6473   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3865   -0.5750   -1.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5980   -1.2660    0.1915 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.3512   -2.1442    1.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847    0.1730    1.2695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0607   -1.6994   -0.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.6237   -1.5097 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7549    0.0902   -2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.5689   -2.6665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5225    0.5286   -0.9701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0546    0.2020    0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.2027    0.6519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0830    1.2088   -0.3843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450    1.5451    0.2156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4398    1.1222   -0.5473 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5603    1.8463   -0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4715    1.0709   -1.3783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9326   -0.1347   -1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4513   -1.2487   -2.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7889   -1.3026   -2.7306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6369   -2.3115   -2.3303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702   -2.2569   -1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8854   -1.1677   -1.2060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6654   -0.0713   -1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2652    0.6347    1.4815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1070    1.0765    2.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1217   -0.2122    2.8769 P   0  0  0  0  0  5  0  0  0  0  0  0
   -7.2442   -0.2208    4.3994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6493   -0.0394    2.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4247   -1.6870    2.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8308    0.5240    1.8543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5088    1.1161    3.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2385    1.5296   -1.6865 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7919    2.5131   -2.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8017    2.3459   -0.5160 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1602    3.5815   -0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2181   -0.0017    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -0.9133    2.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2084   -1.4029    1.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9428   -3.1006   -0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1030   -1.7171   -0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2207    0.5437   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1788    2.2489    1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902    1.3031   -1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1576   -1.1651   -0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -1.1535   -1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972    0.8963    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850   -2.1326   -2.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196    0.2881    1.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.7945    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745    2.1551    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    2.5779    0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7440    2.8552   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0944   -1.7794   -3.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5784   -0.8200   -2.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7265   -3.1421   -1.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6345   -0.3833    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6472    0.2538    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7922   -2.1015    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -0.5686    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.3631    3.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9223    0.9425   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6384    2.7718   -3.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8579    2.5037   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094    3.6143   -1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000    0.2764    3.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1654   -1.3786    3.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2239   -1.2033    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061   -2.5314    1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 23 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 36 39  1  0
 34 40  1  0
 40 41  1  0
  9 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
  6 46  1  0
 46 47  2  0
 47 48  1  0
 48  4  1  0
 44  7  1  0
 40 21  1  0
 33 24  1  0
 33 27  1  0
  1 49  1  0
  1 50  1  0
  5 51  1  0
  7 52  1  1
  9 53  1  6
 10 54  1  0
 10 55  1  0
 14 56  1  0
 18 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  1
 23 61  1  1
 25 62  1  0
 29 63  1  0
 29 64  1  0
 31 65  1  0
 34 66  1  6
 38 67  1  0
 39 68  1  0
 40 69  1  1
 41 70  1  0
 42 71  1  6
 43 72  1  0
 44 73  1  6
 45 74  1  0
 46 75  1  0
 47 76  1  0
 48 77  1  0
 48 78  1  0
M  END
Download

PDB for HMDB0000221 (NADPH)

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+0
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+0
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
Download

3D PDB for HMDB0000221 (NADPH)

COMPND    HMDB0000221
HETATM    1  N1  UNL     1      10.153  -2.102  -0.481  1.00  0.00           N  
HETATM    2  C1  UNL     1       9.100  -1.164  -0.601  1.00  0.00           C  
HETATM    3  O1  UNL     1       8.954  -0.555  -1.731  1.00  0.00           O  
HETATM    4  C2  UNL     1       8.150  -0.806   0.442  1.00  0.00           C  
HETATM    5  C3  UNL     1       7.225   0.099   0.173  1.00  0.00           C  
HETATM    6  N2  UNL     1       6.235   0.551   1.074  1.00  0.00           N  
HETATM    7  C4  UNL     1       5.291   1.543   0.664  1.00  0.00           C  
HETATM    8  O2  UNL     1       4.050   1.182   0.304  1.00  0.00           O  
HETATM    9  C5  UNL     1       4.178   0.814  -1.104  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.806  -0.647  -1.084  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.386  -0.575  -1.088  1.00  0.00           O  
HETATM   12  P1  UNL     1       1.598  -1.266   0.191  1.00  0.00           P  
HETATM   13  O4  UNL     1       2.351  -2.144   1.101  1.00  0.00           O  
HETATM   14  O5  UNL     1       1.285   0.173   1.269  1.00  0.00           O  
HETATM   15  O6  UNL     1       0.061  -1.699  -0.259  1.00  0.00           O  
HETATM   16  P2  UNL     1      -0.411  -0.624  -1.510  1.00  0.00           P  
HETATM   17  O7  UNL     1       0.755   0.090  -2.119  1.00  0.00           O  
HETATM   18  O8  UNL     1      -1.233  -1.569  -2.666  1.00  0.00           O  
HETATM   19  O9  UNL     1      -1.523   0.529  -0.970  1.00  0.00           O  
HETATM   20  C7  UNL     1      -2.055   0.202   0.244  1.00  0.00           C  
HETATM   21  C8  UNL     1      -3.138   1.203   0.652  1.00  0.00           C  
HETATM   22  O10 UNL     1      -4.083   1.209  -0.384  1.00  0.00           O  
HETATM   23  C9  UNL     1      -5.245   1.545   0.216  1.00  0.00           C  
HETATM   24  N3  UNL     1      -6.440   1.122  -0.547  1.00  0.00           N  
HETATM   25  C10 UNL     1      -7.560   1.846  -0.718  1.00  0.00           C  
HETATM   26  N4  UNL     1      -8.471   1.071  -1.378  1.00  0.00           N  
HETATM   27  C11 UNL     1      -7.933  -0.135  -1.624  1.00  0.00           C  
HETATM   28  C12 UNL     1      -8.451  -1.249  -2.248  1.00  0.00           C  
HETATM   29  N5  UNL     1      -9.789  -1.303  -2.731  1.00  0.00           N  
HETATM   30  N6  UNL     1      -7.637  -2.311  -2.330  1.00  0.00           N  
HETATM   31  C13 UNL     1      -6.370  -2.257  -1.811  1.00  0.00           C  
HETATM   32  N7  UNL     1      -5.885  -1.168  -1.206  1.00  0.00           N  
HETATM   33  C14 UNL     1      -6.665  -0.071  -1.099  1.00  0.00           C  
HETATM   34  C15 UNL     1      -5.265   0.635   1.481  1.00  0.00           C  
HETATM   35  O11 UNL     1      -6.107   1.076   2.440  1.00  0.00           O  
HETATM   36  P3  UNL     1      -7.122  -0.212   2.877  1.00  0.00           P  
HETATM   37  O12 UNL     1      -7.244  -0.221   4.399  1.00  0.00           O  
HETATM   38  O13 UNL     1      -8.649  -0.039   2.236  1.00  0.00           O  
HETATM   39  O14 UNL     1      -6.425  -1.687   2.459  1.00  0.00           O  
HETATM   40  C16 UNL     1      -3.831   0.524   1.854  1.00  0.00           C  
HETATM   41  O15 UNL     1      -3.509   1.116   3.043  1.00  0.00           O  
HETATM   42  C17 UNL     1       5.239   1.530  -1.687  1.00  0.00           C  
HETATM   43  O16 UNL     1       4.792   2.513  -2.655  1.00  0.00           O  
HETATM   44  C18 UNL     1       5.802   2.346  -0.516  1.00  0.00           C  
HETATM   45  O17 UNL     1       5.160   3.582  -0.495  1.00  0.00           O  
HETATM   46  C19 UNL     1       6.218  -0.002   2.379  1.00  0.00           C  
HETATM   47  C20 UNL     1       7.150  -0.913   2.687  1.00  0.00           C  
HETATM   48  C21 UNL     1       8.208  -1.403   1.773  1.00  0.00           C  
HETATM   49  H1  UNL     1       9.943  -3.101  -0.576  1.00  0.00           H  
HETATM   50  H2  UNL     1      11.103  -1.717  -0.319  1.00  0.00           H  
HETATM   51  H3  UNL     1       7.221   0.544  -0.789  1.00  0.00           H  
HETATM   52  H4  UNL     1       5.179   2.249   1.550  1.00  0.00           H  
HETATM   53  H5  UNL     1       3.190   1.303  -1.550  1.00  0.00           H  
HETATM   54  H6  UNL     1       4.158  -1.165  -0.191  1.00  0.00           H  
HETATM   55  H7  UNL     1       4.113  -1.154  -1.986  1.00  0.00           H  
HETATM   56  H8  UNL     1       1.097   0.896   0.586  1.00  0.00           H  
HETATM   57  H9  UNL     1      -1.885  -2.133  -2.146  1.00  0.00           H  
HETATM   58  H10 UNL     1      -1.320   0.288   1.095  1.00  0.00           H  
HETATM   59  H11 UNL     1      -2.509  -0.795   0.197  1.00  0.00           H  
HETATM   60  H12 UNL     1      -2.775   2.155   0.972  1.00  0.00           H  
HETATM   61  H13 UNL     1      -5.360   2.578   0.517  1.00  0.00           H  
HETATM   62  H14 UNL     1      -7.744   2.855  -0.401  1.00  0.00           H  
HETATM   63  H15 UNL     1     -10.094  -1.779  -3.579  1.00  0.00           H  
HETATM   64  H16 UNL     1     -10.578  -0.820  -2.183  1.00  0.00           H  
HETATM   65  H17 UNL     1      -5.726  -3.142  -1.901  1.00  0.00           H  
HETATM   66  H18 UNL     1      -5.635  -0.383   1.094  1.00  0.00           H  
HETATM   67  H19 UNL     1      -8.647   0.254   1.313  1.00  0.00           H  
HETATM   68  H20 UNL     1      -6.792  -2.102   1.669  1.00  0.00           H  
HETATM   69  H21 UNL     1      -3.557  -0.569   1.842  1.00  0.00           H  
HETATM   70  H22 UNL     1      -3.310   0.363   3.705  1.00  0.00           H  
HETATM   71  H23 UNL     1       5.922   0.943  -2.263  1.00  0.00           H  
HETATM   72  H24 UNL     1       5.638   2.772  -3.078  1.00  0.00           H  
HETATM   73  H25 UNL     1       6.858   2.504  -0.536  1.00  0.00           H  
HETATM   74  H26 UNL     1       4.409   3.614  -1.154  1.00  0.00           H  
HETATM   75  H27 UNL     1       5.500   0.276   3.167  1.00  0.00           H  
HETATM   76  H28 UNL     1       7.165  -1.379   3.679  1.00  0.00           H  
HETATM   77  H29 UNL     1       9.224  -1.203   2.190  1.00  0.00           H  
HETATM   78  H30 UNL     1       8.106  -2.531   1.711  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   46
CONECT    7    8   44   52
CONECT    8    9
CONECT    9   10   42   53
CONECT   10   11   54   55
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   56
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   57
CONECT   19   20
CONECT   20   21   58   59
CONECT   21   22   40   60
CONECT   22   23
CONECT   23   24   34   61
CONECT   24   25   33
CONECT   25   26   26   62
CONECT   26   27
CONECT   27   28   28   33
CONECT   28   29   30
CONECT   29   63   64
CONECT   30   31   31
CONECT   31   32   65
CONECT   32   33   33
CONECT   34   35   40   66
CONECT   35   36
CONECT   36   37   37   38   39
CONECT   38   67
CONECT   39   68
CONECT   40   41   69
CONECT   41   70
CONECT   42   43   44   71
CONECT   43   72
CONECT   44   45   73
CONECT   45   74
CONECT   46   47   47   75
CONECT   47   48   76
CONECT   48   77   78
END
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SMILES for HMDB0000221 (NADPH)

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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
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INCHI for HMDB0000221 (NADPH)

InChI=1S/C21H30N7O17P3/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/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Dihydronicotinamide-adenine dinucleotide phosphateChEBI
NADPH dihydro-nicotinamide-adenine-dinucleotide phosphATEChEBI
Reduced nicotinamide adenine dinucleotide phosphateChEBI
Reduced nicotinamide-adenine dinucleotide phosphateChEBI
TPNHChEBI
Dihydronicotinamide-adenine dinucleotide phosphoric acidGenerator
NADPH dihydro-nicotinamide-adenine-dinucleotide phosphoric acidGenerator
Reduced nicotinamide adenine dinucleotide phosphoric acidGenerator
Reduced nicotinamide-adenine dinucleotide phosphoric acidGenerator
Coenzyme IIMeSH
Nicotinamide-adenine dinucleotide phosphateMeSH
Nucleotide, triphosphopyridineMeSH
Triphosphopyridine nucleotideMeSH
Dinucleotide phosphate, nicotinamide-adenineMeSH
NADPMeSH
Nicotinamide adenine dinucleotide phosphateMeSH
Phosphate, nicotinamide-adenine dinucleotideMeSH
Nadph dihydro-nicotinamide-adenine-dinucleotidephosphoric acidGenerator
NADPHHMDB
Nicotinamide-adenine dinucleotide phosphate, reducedHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide, reducedHMDB
beta-NADPHHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-TPNHHMDB
β-NADPHHMDB
β-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
β-TPNHHMDB
Chemical FormulaC21H30N7O17P3
Average Molecular Weight745.4209
Monoisotopic Molecular Weight745.091102105
IUPAC Name{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Namenadph
CAS Registry Number53-57-6
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](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C21H30N7O17P3/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/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyACFIXJIJDZMPPO-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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine nucleotide sugar
  • Purine ribonucleoside 2',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Nicotinamide-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • N-substituted nicotinamide
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Imidazopyrimidine
  • Dihydropyridinecarboxylic acid derivative
  • Purine
  • Dihydropyridine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • N-substituted imidazole
  • Phosphoric acid ester
  • Hydropyridine
  • Alkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Imidolactam
  • Pyrimidine
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Enamine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.45 g/LALOGPS
logP-1.1ALOGPS
logP-6.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m³·mol⁻¹ChemAxon
Polarizability63.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+221.17630932474
DeepCCS[M-H]-219.28130932474
DeepCCS[M-2H]-252.76330932474
DeepCCS[M+Na]+226.79730932474
AllCCS[M+H]+237.932859911
AllCCS[M+H-H2O]+237.632859911
AllCCS[M+NH4]+238.032859911
AllCCS[M+Na]+238.032859911
AllCCS[M-H]-234.032859911
AllCCS[M+Na-2H]-236.532859911
AllCCS[M+HCOO]-239.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.6 minutes32390414
Predicted by Siyang on May 30, 202211.0014 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20229.01 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid581.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid702.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid221.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid48.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid182.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid70.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid363.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid342.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1004.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid640.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid142.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid771.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid226.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid334.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate765.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA493.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water725.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NADPHNC(=O)C1=CN(C=CC1)[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]1O5599.8Standard polar33892256
NADPHNC(=O)C1=CN(C=CC1)[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]1O3976.0Standard non polar33892256
NADPHNC(=O)C1=CN(C=CC1)[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]1O6479.9Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified51.0 (34.0-81.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02338
Phenol Explorer Compound IDNot Available
FooDB IDFDB021909
KNApSAcK IDC00019545
Chemspider ID5673
KEGG Compound IDC00005
BioCyc IDNADPH
BiGG IDNot Available
Wikipedia LinkNicotinamide adenine dinucleotide phosphate
METLIN ID3691
PubChem Compound5884
PDB IDNot Available
ChEBI ID16474
Food Biomarker OntologyNot Available
VMH IDNADPH
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSeelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Letters (1996), 37(9), 1377-80.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  2. Shindo Y, Witt E, Han D, Epstein W, Packer L: Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol. 1994 Jan;102(1):122-4. [PubMed:8288904 ]
  3. Iwata H, Tezuka Y, Kadota S, Hiratsuka A, Watabe T: Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. Drug Metab Pharmacokinet. 2005 Feb;20(1):34-45. [PubMed:15770073 ]
  4. Birkmayer GJ, Birkmayer W: Stimulation of endogenous L-dopa biosynthesis--a new principle for the therapy of Parkinson's disease. The clinical effect of nicotinamide adenine dinucleotide (NADH) and nicotinamide adenine dinucleotidephosphate (NADPH). Acta Neurol Scand Suppl. 1989;126:183-7. [PubMed:2618590 ]
  5. Lee AJ, Zhu BT: NADPH-dependent formation of polar and nonpolar estrogen metabolites following incubations of 17 beta-estradiol with human liver microsomes. Drug Metab Dispos. 2004 Aug;32(8):876-83. [PubMed:15258114 ]
  6. Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23. [PubMed:16183782 ]
  7. Karanam BV, Hop CE, Liu DQ, Wallace M, Dean D, Satoh H, Komuro M, Awano K, Vincent SH: In vitro metabolism of MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl) phenyl]methyl]benzamide], a peroxisome proliferator-activated receptor alpha/gamma agonist. I. Role of cytochrome P450, methyltransferases, flavin monooxygenases, and esterases. Drug Metab Dispos. 2004 Sep;32(9):1015-22. [PubMed:15319344 ]
  8. Soglia JR, Contillo LG, Kalgutkar AS, Zhao S, Hop CE, Boyd JG, Cole MJ: A semiquantitative method for the determination of reactive metabolite conjugate levels in vitro utilizing liquid chromatography-tandem mass spectrometry and novel quaternary ammonium glutathione analogues. Chem Res Toxicol. 2006 Mar;19(3):480-90. [PubMed:16544956 ]
  9. Afanas'ev IB, Suslova TB, Cheremisina ZP, Abramova NE, Korkina LG: Study of antioxidant properties of metal aspartates. Analyst. 1995 Mar;120(3):859-62. [PubMed:7741242 ]
  10. Lin CC, Wong BK, Burgey CS, Gibson CR, Singh R: In vitro metabolism of a thrombin inhibitor and quantitation of metabolically generated cyanide. J Pharm Biomed Anal. 2005 Oct 4;39(5):1014-20. Epub 2005 Jul 14. [PubMed:16023819 ]
  11. Conley AJ, Pattison JC, Bird IM: Variations in adrenal androgen production among (nonhuman) primates. Semin Reprod Med. 2004 Nov;22(4):311-26. [PubMed:15635499 ]

Only showing the first 10 proteins. There are 203 proteins in total.

Show all enzymes and transporters

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] + NADPHdetails
Acyl-[acyl-carrier-protein] + NADP → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPHdetails
Butyryl-[acp] + NADP → But-2-enoyl-[acyl-carrier protein] + NADPH + Hydrogen Iondetails
(3R)-3-Hydroxybutanoyl-[acyl-carrier protein] + NADP → Acetoacetyl-[acp] + NADPH + Hydrogen Iondetails
(3R)-3-Hydroxydecanoyl-[acyl-carrier protein] + NADP → 3-Oxodecanoyl-[acp] + NADPHdetails
(3R)-3-Hydroxyoctanoyl-[acyl-carrier protein] + NADP → 3-Oxooctanoyl-[acp] + NADPH + Hydrogen Iondetails
(3R)-3-Hydroxypalmitoyl-[acyl-carrier protein] + NADP → 3-Oxohexadecanoyl-[acp] + NADPH + Hydrogen Iondetails
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + NADP → 3-Oxotetradecanoyl-[acp] + NADPH + Hydrogen Iondetails
Dodecanoyl-[acyl-carrier protein] + NADP → trans-Dodec-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
(R)-3-Hydroxyhexanoyl-[acp] + NADP → 3-Oxohexanoyl-[acp] + NADPH + Hydrogen Iondetails
Hexanoyl-[acp] + NADP → trans-Hex-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
Octanoyl-[acp] + NADP → trans-Oct-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
Decanoyl-[acp] + NADP → trans-Dec-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
Tetradecanoyl-[acp] + NADP → trans-Tetradec-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
Hexadecanoyl-[acp] + NADP → trans-Hexadec-2-enoyl-[acp] + NADPH + Hydrogen Iondetails
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 Iondetails
Malonic semialdehyde + Coenzyme A + NADP → Malonyl-CoA + NADPH + Hydrogen Iondetails
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 + NADPHdetails
Androsterone + NADP → Androstanedione + NADPH + Hydrogen Iondetails
Etiocholanolone + NADP → Etiocholanedione + NADPH + Hydrogen Iondetails
3a,7a-Dihydroxy-5b-cholestane + NADP → 7a-Hydroxy-5b-cholestan-3-one + NADPH + Hydrogen Iondetails
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADP → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADPH + Hydrogen Iondetails
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + Hydrogen Ion + NADPH → Tetrahydrocortisone + NADPdetails
Tetrahydrocortisol + NADP → Dihydrocortisol + NADPH + Hydrogen Iondetails
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NADP → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADPH + Hydrogen Iondetails
Tetrahydrocorticosterone + NADP → 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH + Hydrogen Iondetails
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADP → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADPH + Hydrogen Iondetails
3a-Hydroxy-5b-pregnane-20-one + NADP → 5a-Pregnane-3,20-dione + NADPH + Hydrogen Iondetails
Dihydrotestosterone + NADPH + Hydrogen Ion → Androstan-3alpha,17beta-diol + NADPdetails
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' + NADPHdetails
(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 + NADPHdetails
(13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate + NADP → (13E)-11-alpha-hydroxy-9,15-dioxoprost-13-enoate + NADPHdetails
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADPdetails
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' + NADPHdetails
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' + NADPHdetails
Prostaglandin F2a + NADP → Prostaglandin E2 + NADPH + Hydrogen Iondetails
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADPdetails
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 Iondetails
beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADPdetails
D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Iondetails
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Iondetails
Sorbitol + NADP → alpha-D-Glucose + NADPH + Hydrogen Iondetails
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Iondetails
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 + NADPHdetails
Thioredoxin + NADP → Thioredoxin disulfide + NADPH + Hydrogen Iondetails
Hydrogen selenide + NADP + Water → Selenite + NADPH + Hydrogen Iondetails
NADPH + Hydrogen Ion + Methylselenic acid → NADP + Water + Methaneselenoldetails
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 + Waterdetails
Episterol + NADP → 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Iondetails
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 + Waterdetails
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Tamoxifen + Oxygen + NADPH + Hydrogen Ion → Tamoxifen N-oxide + NADP + Waterdetails

Only showing the first 10 proteins. There are 203 proteins in total.

Show all enzymes and transporters