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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
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
Nadph dihydro-nicotinamide-adenine-dinucleotidephosphoric acidGenerator
Coenzyme IIMeSH
Dinucleotide phosphate, nicotinamide-adenineMeSH
NADPMeSH
Nicotinamide adenine dinucleotide phosphateMeSH
Nicotinamide-adenine dinucleotide phosphateMeSH
Nucleotide, triphosphopyridineMeSH
Phosphate, nicotinamide-adenine dinucleotideMeSH
Triphosphopyridine nucleotideMeSH
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
Not AvailableNot 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 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

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADPH GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-02tj-1838493720-b38b37650e8976905bb02019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4r-0841393100-6e4cbc8ac576e3e8b1952019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0550-2694875730-0dc522520957880672cb2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 15V, negative-QTOFsplash10-0006-0000000900-1448a5a4a9a9ec30bc1d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 17V, negative-QTOFsplash10-0006-0000000900-84c6720ae2b6d0d9ca352020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 20V, negative-QTOFsplash10-0006-0000100900-4ddda02ddc90d193fba12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 23V, negative-QTOFsplash10-0006-0000201900-cbb70a91b1ac1fcb6e182020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 25V, negative-QTOFsplash10-0006-0001301900-2ec6727d0b32f09b91b62020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 27V, negative-QTOFsplash10-0006-0101502900-1d110f57242fe6b3d4eb2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 30V, negative-QTOFsplash10-054o-1213903700-aa4ca72e492f0f0b7f752020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 33V, negative-QTOFsplash10-0a6u-1313903400-9a6e4df99ff5a68effea2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 35V, negative-QTOFsplash10-0a6r-1324903300-069588f3537afa016ac82020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 40V, negative-QTOFsplash10-0a6r-3535903000-746e661fe41dfe08b6d12020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADPH QTOF 45V, negative-QTOFsplash10-0a6r-5946701000-9407142d1340518483bf2020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 10V, Positive-QTOFsplash10-000i-0921103300-a94dc77e4683c53f1e1c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 20V, Positive-QTOFsplash10-000i-0901000000-5fcc7bc2ff00254e837a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 40V, Positive-QTOFsplash10-000i-0920000000-91a94a0d16f7db6907e12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 10V, Negative-QTOFsplash10-0036-6900111800-7f73a4ecf431645a13cf2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 20V, Negative-QTOFsplash10-003r-3901000000-b9bf964190caf0afebde2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 40V, Negative-QTOFsplash10-057i-6900000000-f6e201cd60ed9314f31a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 10V, Positive-QTOFsplash10-000i-0900000200-c30f8bbbadabff3b10f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 20V, Positive-QTOFsplash10-000i-0911003300-322bf2f4fc18dbf667d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 40V, Positive-QTOFsplash10-002r-1901300000-6129e75df61dcc44c45a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 10V, Negative-QTOFsplash10-0006-0000000900-b62da30b8e49b793af7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADPH 20V, Negative-QTOFsplash10-004i-8301205900-8cec7794d03fc25fae8b2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
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.

Enzymes

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
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
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
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
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
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
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
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
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
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.