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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-23 02:53:08 UTC
Secondary Accession Numbers
  • HMDB0000799
  • HMDB0006341
  • HMDB00221
  • HMDB00799
  • HMDB06341
Metabolite Identification
Common NameNADPH
DescriptionNicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Dihydrocodehydrogenase IIHMDB
Dihydronicotinamide adenine dinucleotide phosphateHMDB
Dihydronicotinamide adenine dinucleotide-PHMDB
Dihydrotriphosphopyridine nucleotide reducedHMDB
Nicotinamide adenine dinucleotide phosphate - reducedHMDB
Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Reduced codehydrase IIHMDB
Reduced coenzyme IIHMDB
Reduced cozymase IIHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide reducedHMDB
Chemical FormulaC21H30N7O17P3
Average Molecular Weight745.4209
Monoisotopic Molecular Weight745.091102105
IUPAC Name{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-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 Name[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number53-57-6
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
  • (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
  • Monosaccharide phosphate
  • 6-aminopurine
  • N-substituted nicotinamide
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Dihydropyridine
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Pyrimidine
  • N-substituted imidazole
  • Hydropyridine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidolactam
  • Monosaccharide
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Enamine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Biological location:


  Biofluid and excreta:

  Tissue and substructures:


Route of exposure:





Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility5.45 g/LALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4.92ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m³·mol⁻¹ChemAxon
Polarizability60.22 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9421780200-89062ec4778392672634View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02tj-1838493720-b38b37650e8976905bb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0550-2694875730-0dc522520957880672cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921104300-c1952197674952109d2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-31adeef6c90e9070dfa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-e29dcab04f59f9c7189cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-6900111800-ab3c73d03c4430e1b644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4901100000-96b551ade48c419935edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-0898019fd8b891d5245eView in MoNA
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
21-hydroxylase deficiency (CYP21)ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
27-Hydroxylase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
5-OxoprolinuriaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BloodDetected and Quantified51.0 (34.0-81.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021909
KNApSAcK IDNot Available
Chemspider ID17215925
KEGG Compound IDC00005
BiGG ID33486
Wikipedia LinkNot Available
PubChem Compound22833512
PDB IDNot Available
ChEBI ID16474
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.


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:
Uniprot ID:
Molecular weight:
(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
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
Uniprot ID:
Molecular weight:
Malonic semialdehyde + Coenzyme A + NADP → Acetyl-CoA + Carbon dioxide + NADPH + Hydrogen Iondetails
Malonic semialdehyde + Coenzyme A + NADP → Malonyl-CoA + NADPH + Hydrogen Iondetails
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:
Uniprot ID:
Molecular weight:
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
5-b-Cholestane-3a ,7a ,12a-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
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:
Uniprot ID:
Molecular weight:
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
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:
Uniprot ID:
Molecular weight:
R-CHOH-R' + NADP → R-CO-R' + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:
Uniprot ID:
Molecular weight:
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
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:
Uniprot ID:
Molecular weight:
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
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:
Uniprot ID:
Molecular weight:
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
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
Uniprot ID:
Molecular weight:
Lathosterol + NADPH + Hydrogen Ion + Oxygen → 7-Dehydrocholesterol + NADP + Waterdetails
Episterol + NADP → 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Iondetails
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:
Uniprot ID:
Molecular weight:
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.