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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
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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