Human Metabolome Database Version 3.5

Showing metabocard for NADPH (HMDB00221)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:06 -0700
HMDB ID HMDB00221
Secondary Accession Numbers
  • HMDB00799
  • HMDB06341
Metabolite Identification
Common Name NADPH
Description Nicotinamide 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.).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
  2. 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
  3. Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
  4. Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
  5. b-NADPH
  6. b-Nicotinamide-adenine-dinucleotide-phosphorate
  7. b-Nicotinamide-adenine-dinucleotide-phosphoric acid
  8. beta-NADPH
  9. beta-Nicotinamide-adenine-dinucleotide-phosphorate
  10. beta-Nicotinamide-adenine-dinucleotide-phosphoric acid
  11. Dihydrocodehydrogenase II
  12. Dihydronicotinamide adenine dinucleotide phosphate
  13. Dihydronicotinamide adenine dinucleotide-P
  14. Dihydrotriphosphopyridine nucleotide reduced
  15. NADP-reduced
  16. NADPH
  17. Nicotinamide adenine dinucleotide phosphate - reduced
  18. Nicotinamide-adenine-dinucleotide-phosphorate
  19. Nicotinamide-adenine-dinucleotide-phosphoric acid
  20. Reduced Codehydrase II
  21. Reduced Coenzyme II
  22. Reduced Cozymase II
  23. Reduced triphosphopyridine nucleotide
  24. Triphosphopyridine nucleotide reduced
Chemical Formula C21H30N7O17P3
Average Molecular Weight 745.4209
Monoisotopic Molecular Weight 745.091102105
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 IUPAC 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 Number 53-57-6
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=C(N)N=CN=C23)[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-/m0/s1
InChI Key ACFIXJIJDZMPPO-NCHANQSKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Dihydropyridine
  • Disaccharide Phosphate
  • Enamine
  • Glycosyl Compound
  • Hemiaminal
  • Hydropyridine
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Nicotinamide Nucleotide
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Disaccharide
  • Phosphoric Acid Ester
  • Primary Carboxylic Acid Amide
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct Parent Purine Ribonucleoside 2',5'-Bisphosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Androgen and estrogen metabolism
  • Component of Arginine and proline metabolism
  • Component of Bile acid biosynthesis
  • Component of C21-Steroid hormone metabolism
  • Component of Folate biosynthesis
  • Component of Fructose and mannose metabolism
  • Component of Glutamate metabolism
  • Component of Glutathione metabolism
  • Component of Glycerolipid metabolism
  • Component of Glyoxylate and dicarboxylate metabolism
  • Component of Monoterpenoid biosynthesis
  • Component of Nicotinate and nicotinamide metabolism
  • Component of Pantothenate and CoA biosynthesis
  • Component of Porphyrin and chlorophyll metabolism
  • Component of Prostaglandin and leukotriene metabolism
  • Component of Purine metabolism
  • Component of Pyrimidine metabolism
  • Component of Pyruvate metabolism
  • Component of beta-Alanine metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 5.45 g/L ALOGPS
LogP -1.13 ALOGPS
LogP -7.5 ChemAxon
LogS -2.14 ALOGPS
pKa (strongest acidic) 0.66 ChemAxon
pKa (strongest basic) 4.92 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 364.15 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 153.87 ChemAxon
Polarizability 60.22 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Histidine Metabolism SMP00044 map00340 Link_out
Glycerolipid Metabolism SMP00039 map00561 Link_out
Glucose-Alanine Cycle SMP00127 Not Available
Glutathione Metabolism SMP00015 map00480 Link_out
Phytanic Acid Peroxisomal Oxidation SMP00450 Not Available
Ethanol Degradation SMP00449 Not Available
Vitamin K Metabolism SMP00464 Not Available
Transfer of Acetyl Groups into Mitochondria SMP00466 Not Available
Plasmalogen Synthesis SMP00479 Not Available
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Pterine Biosynthesis SMP00005 map00790 Link_out
Folate Metabolism SMP00053 map00670 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
51.0 (34.0-81.0) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021909
KNApSAcK ID Not Available
Chemspider ID 17215925 Link_out
KEGG Compound ID C00005 Link_out
BioCyc ID NADPH Link_out
BiGG ID 33486 Link_out
Wikipedia Link NADPH Link_out
NuGOwiki Link HMDB00221 Link_out
Metagene Link HMDB00221 Link_out
METLIN ID 3691 Link_out
PubChem Compound 22833512 Link_out
PDB ID Not Available
ChEBI ID 16474 Link_out
References
Synthesis Reference Seelbach, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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(1):18. Pubmed: 15882454 Link_out
  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-trifluoromet hyl) 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 203 enzymes in total.

Name: Fatty acid synthase
Reactions:
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP unknown 3-oxoacyl-[acyl-carrier-protein] + NADPH details
Acyl-[acyl-carrier-protein] + NADP unknown trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPH details
Butyryl-[acp] + NADP unknown But-2-enoyl-[acyl-carrier protein] + NADPH + Hydrogen Ion details
(3R)-3-Hydroxybutanoyl-[acyl-carrier protein] + NADP unknown Acetoacetyl-[acp] + NADPH + Hydrogen Ion details
(3R)-3-Hydroxydecanoyl-[acyl-carrier protein] + NADP unknown 3-Oxodecanoyl-[acp] + NADPH details
(3R)-3-Hydroxyoctanoyl-[acyl-carrier protein] + NADP unknown 3-Oxooctanoyl-[acp] + NADPH + Hydrogen Ion details
(3R)-3-Hydroxypalmitoyl-[acyl-carrier protein] + NADP unknown 3-Oxohexadecanoyl-[acp] + NADPH + Hydrogen Ion details
(3R)-3-Hydroxytetradecanoyl-[acyl-carrier protein] + NADP unknown 3-Oxotetradecanoyl-[acp] + NADPH + Hydrogen Ion details
Dodecanoyl-[acyl-carrier protein] + NADP unknown trans-Dodec-2-enoyl-[acp] + NADPH + Hydrogen Ion details
(R)-3-Hydroxyhexanoyl-[acp] + NADP unknown 3-Oxohexanoyl-[acp] + NADPH + Hydrogen Ion details
Hexanoyl-[acp] + NADP unknown trans-Hex-2-enoyl-[acp] + NADPH + Hydrogen Ion details
Octanoyl-[acp] + NADP unknown trans-Oct-2-enoyl-[acp] + NADPH + Hydrogen Ion details
Decanoyl-[acp] + NADP unknown trans-Dec-2-enoyl-[acp] + NADPH + Hydrogen Ion details
Tetradecanoyl-[acp] + NADP unknown trans-Tetradec-2-enoyl-[acp] + NADPH + Hydrogen Ion details
Hexadecanoyl-[acp] + NADP unknown trans-Hexadec-2-enoyl-[acp] + NADPH + Hydrogen Ion details
Gene Name: FASN
Uniprot ID: P49327 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
Reactions:
Malonic semialdehyde + Coenzyme A + NADP unknown Acetyl-CoA + Carbon dioxide + NADPH + Hydrogen Ion details
Malonic semialdehyde + Coenzyme A + NADP unknown Malonyl-CoA + NADPH + Hydrogen Ion details
Gene Name: ALDH6A1
Uniprot ID: Q02252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C4
Reactions:
Chlordecone alcohol + NADP unknown Chlordecone + NADPH details
Androsterone + NADP unknown Androstanedione + NADPH + Hydrogen Ion details
Etiocholanolone + NADP unknown Etiocholanedione + NADPH + Hydrogen Ion details
3a,7a-Dihydroxy-5b-cholestane + NADP unknown 7a-Hydroxy-5b-cholestan-3-one + NADPH + Hydrogen Ion details
5-b-Cholestane-3a ,7a ,12a-triol + NADP unknown 7a,12a-Dihydroxy-5b-cholestan-3-one + NADPH + Hydrogen Ion details
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + Hydrogen Ion + NADPH unknown Tetrahydrocortisone + NADP details
Tetrahydrocortisol + NADP unknown Dihydrocortisol + NADPH + Hydrogen Ion details
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NADP unknown 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADPH + Hydrogen Ion details
Tetrahydrocorticosterone + NADP unknown 11b,21-Dihydroxy-5b-pregnane-3,20-dione + NADPH + Hydrogen Ion details
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADP unknown 21-Hydroxy-5b-pregnane-3,11,20-trione + NADPH + Hydrogen Ion details
3a-Hydroxy-5b-pregnane-20-one + NADP unknown 5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion details
Dihydrotestosterone + NADPH + Hydrogen Ion unknown Androstan-3alpha,17beta-diol + NADP details
Gene Name: AKR1C4
Uniprot ID: P17516 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbonyl reductase [NADPH] 1
Reactions:
R-CHOH-R' + NADP unknown R-CO-R' + NADPH details
(5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate + NADP unknown (5Z,13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate + NADPH details
(13E)-(15S)-11-alpha,15-dihydroxy-9-oxoprost-13-enoate + NADP unknown (13E)-11-alpha-hydroxy-9,15-dioxoprost-13-enoate + NADPH details
Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion unknown 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP details
Gene Name: CBR1
Uniprot ID: P16152 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dehydrogenase/reductase SDR family member 4
Reactions:
R-CHOH-R' + NADP unknown R-CO-R' + NADPH details
Gene Name: DHRS4
Uniprot ID: Q9BTZ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbonyl reductase [NADPH] 3
Reactions:
R-CHOH-R' + NADP unknown R-CO-R' + NADPH details
Prostaglandin F2a + NADP unknown Prostaglandin E2 + NADPH + Hydrogen Ion details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion unknown 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP details
Gene Name: CBR3
Uniprot ID: O75828 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldose reductase
Reactions:
Glycerol + NADP unknown Glyceraldehyde + NADPH + Hydrogen Ion details
Beta-D-Galactose + NADPH + Hydrogen Ion unknown Galactitol + NADP details
D-Xylitol + NADP unknown D-Xylose + NADPH + Hydrogen Ion details
L-Arabitol + NADP unknown L-Arabinose + NADPH + Hydrogen Ion details
Sorbitol + NADP unknown Alpha-D-Glucose + NADPH + Hydrogen Ion details
Propylene glycol + NADP unknown Lactaldehyde + NADPH + Hydrogen Ion details
Gene Name: AKR1B1
Uniprot ID: P15121 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Thioredoxin reductase 1, cytoplasmic
Reactions:
Thioredoxin + NADP unknown thioredoxin disulfide + NADPH details
Thioredoxin + NADP unknown Thioredoxin disulfide + NADPH + Hydrogen Ion details
Hydrogen selenide + NADP + Water unknown Selenite + NADPH + Hydrogen Ion details
NADPH + Hydrogen Ion + Methylselenic acid unknown NADP + Water + Methaneselenol details
Gene Name: TXNRD1
Uniprot ID: Q16881 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lathosterol oxidase
Reactions:
Lathosterol + NADPH + Hydrogen Ion + Oxygen unknown 7-Dehydrocholesterol + NADP + Water details
Episterol + NADP unknown 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Ion details
Gene Name: SC5DL
Uniprot ID: O75845 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylaniline monooxygenase [N-oxide-forming] 5
Reactions:
N,N-Dimethylaniline + NADPH + Oxygen unknown Dimethylaniline-N-oxide + NADP + Water details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion unknown Tamoxifen N-oxide + NADP + Water details
Gene Name: FMO5
Uniprot ID: P49326 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heme oxygenase 2
Reactions: Not Available
Gene Name: HMOX2
Uniprot ID: P30519 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Squalene monooxygenase
Reactions:
Squalene + NADPH + Oxygen unknown (3S)-2,3-epoxy-2,3-dihydrosqualene + NADP + Water details
Squalene + Oxygen + NADPH + Hydrogen Ion unknown (3S)-2,3-epoxy-2,3-dihydrosqualene + NADP + Water details
Gene Name: SQLE
Uniprot ID: Q14534 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylaniline monooxygenase [N-oxide-forming] 2
Reactions:
N,N-Dimethylaniline + NADPH + Oxygen unknown Dimethylaniline-N-oxide + NADP + Water details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion unknown Tamoxifen N-oxide + NADP + Water details
Gene Name: FMO2
Uniprot ID: Q99518 Link_out
Protein Sequence: FASTA
Name: Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial
Reactions:
1-Pyrroline-5-carboxylic acid + NADP + Water unknown L-Glutamic acid + NADPH + Hydrogen Ion details
Pyrroline hydroxycarboxylic acid + NADP + Water unknown 4-Hydroxy-L-glutamic acid + NADPH + Hydrogen Ion details
Gene Name: ALDH4A1
Uniprot ID: P30038 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Thioredoxin reductase 2, mitochondrial
Reactions:
Thioredoxin + NADP unknown thioredoxin disulfide + NADPH details
Thioredoxin + NADP unknown Thioredoxin disulfide + NADPH + Hydrogen Ion details
Hydrogen selenide + NADP + Water unknown Selenite + NADPH + Hydrogen Ion details
NADPH + Hydrogen Ion + Methylselenic acid unknown NADP + Water + Methaneselenol details
Gene Name: TXNRD2
Uniprot ID: Q9NNW7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylaniline monooxygenase [N-oxide-forming] 4
Reactions:
N,N-Dimethylaniline + NADPH + Oxygen unknown Dimethylaniline-N-oxide + NADP + Water details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion unknown Tamoxifen N-oxide + NADP + Water details
Gene Name: FMO4
Uniprot ID: P31512 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylaniline monooxygenase [N-oxide-forming] 3
Reactions:
N,N-Dimethylaniline + NADPH + Oxygen unknown Dimethylaniline-N-oxide + NADP + Water details
Trimethylamine + NADPH + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion unknown Tamoxifen N-oxide + NADP + Water details
Gene Name: FMO3
Uniprot ID: P31513 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NADPH--cytochrome P450 reductase
Reactions:
NADPH + n oxidized hemoprotein unknown NADP + n reduced hemoprotein details
Gene Name: POR
Uniprot ID: P16435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dimethylaniline monooxygenase [N-oxide-forming] 1
Reactions:
N,N-Dimethylaniline + NADPH + Oxygen unknown Dimethylaniline-N-oxide + NADP + Water details
Trimethylamine + NADPH + Hydrogen Ion + Oxygen unknown Trimethylamine N-oxide + NADP + Water details
Tamoxifen + Oxygen + NADPH + Hydrogen Ion unknown Tamoxifen N-oxide + NADP + Water details
Gene Name: FMO1
Uniprot ID: Q01740 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylenetetrahydrofolate reductase
Reactions:
5-Methyltetrahydrofolic acid + NADP unknown 5,10-Methylene-THF + NADPH + Hydrogen Ion details
Gene Name: MTHFR
Uniprot ID: P42898 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione reductase, mitochondrial
Reactions:
Glutathione + NADP unknown Oxidized glutathione + NADPH details
Glutathione + NADP unknown Oxidized glutathione + NADPH + Hydrogen Ion details
Gene Name: GSR
Uniprot ID: P00390 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heme oxygenase 1
Reactions: Not Available
Gene Name: HMOX1
Uniprot ID: P09601 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NADPH:adrenodoxin oxidoreductase, mitochondrial
Reactions:
reduced adrenodoxin + NADP unknown oxidized adrenodoxin + NADPH details
Reduced adrenal ferredoxin + NADP + Hydrogen Ion unknown Oxidized adrenal ferredoxin + NADPH details
Gene Name: FDXR
Uniprot ID: P22570 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Squalene synthase
Reactions:
Presqualene diphosphate + NADPH + Hydrogen Ion unknown Pyrophosphate + Squalene + NADP details
Farnesyl pyrophosphate + NADPH + Hydrogen Ion unknown Squalene + Pyrophosphate + NADP details
Gene Name: FDFT1
Uniprot ID: P37268 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta(14)-sterol reductase
Reactions:
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP unknown 4,4-Dimethylcholesta-8,14,24-trienol + NADPH details
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADP unknown 4,4-Dimethylcholesta-8,14,24-trienol + NADPH + Hydrogen Ion details
Delta 8,14 -Sterol + NADPH + Hydrogen Ion unknown 4a-Methylfecosterol + NADP details
Gene Name: TM7SF2
Uniprot ID: O76062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylsterol monooxygenase 1
Reactions:
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen unknown 4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol + NADP + Water details
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion + Oxygen unknown 3-beta-Hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NADP + Water details
Gene Name: MSMO1
Uniprot ID: Q15800 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating
Reactions:
4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol + NADP unknown 3-Keto-4-methylzymosterol + NADPH + Hydrogen Ion + Carbon dioxide details
Gene Name: NSDHL
Uniprot ID: Q15738 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lanosterol 14-alpha demethylase
Reactions:
Obtusifoliol + Oxygen + NADPH unknown Delta 8,14 -Sterol + Formic acid + NADP + Water details
Lanosterin + Oxygen + NADPH + Hydrogen Ion unknown 4,4-Dimethylcholesta-8,14,24-trienol + Formic acid + NADP + Water details
Obtusifoliol + Oxygen + NADPH + Hydrogen Ion unknown Delta 8,14 -Sterol + Formic acid + NADP + Water details
Gene Name: CYP51A1
Uniprot ID: Q16850 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
4-Aminobutyraldehyde + NADP + Water unknown Gamma-Aminobutyric acid + NADPH + Hydrogen Ion details
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, dimeric NADP-preferring
Reactions:
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Ion details
Phenylacetaldehyde + NADP + Water unknown Phenylacetic acid + NADPH + Hydrogen Ion details
4-Hydroxyphenylacetaldehyde + NADP + Water unknown p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Ion details
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Aldophosphamide + NADP + Water unknown Carboxyphosphamide + NADPH + Hydrogen Ion details
Gene Name: ALDH3A1
Uniprot ID: P30838 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
4-Aminobutyraldehyde + NADP + Water unknown Gamma-Aminobutyric acid + NADPH + Hydrogen Ion details
Betaine aldehyde + NADP + Water unknown Trimethylammonioacetate + NADPH + Hydrogen Ion details
(S)-2-amino-6-oxohexanoate + NADP + Water unknown Aminoadipic acid + NADPH + Hydrogen Ion details
alpha-Aminoadipoyl-S-acyl enzyme + NADPH + Hydrogen Ion unknown (S)-2-amino-6-oxohexanoate + Holo-Lys2 + NADP details
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions:
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Ion details
Phenylacetaldehyde + NADP + Water unknown Phenylacetic acid + NADPH + Hydrogen Ion details
4-Hydroxyphenylacetaldehyde + NADP + Water unknown p-Hydroxyphenylacetic acid + NADPH + Hydrogen Ion details
3,4-Dihydroxyphenylacetaldehyde + NADP + Water unknown 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Ion details
3,4-Dihydroxymandelaldehyde + NADP + Water unknown 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion details
Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water unknown Vanillylmandelic acid + NADPH + Hydrogen Ion details
Aldophosphamide + NADP + Water unknown Carboxyphosphamide + NADPH + Hydrogen Ion details
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
2,5-Dioxopentanoate + NADP + Water unknown Oxoglutaric acid + NADPH + Hydrogen Ion details
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Ion details
4-Aminobutyraldehyde + NADP + Water unknown Gamma-Aminobutyric acid + NADPH + Hydrogen Ion details
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
2,5-Dioxopentanoate + NADP + Water unknown Oxoglutaric acid + NADPH + Hydrogen Ion details
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Ion details
4-Aminobutyraldehyde + NADP + Water unknown Gamma-Aminobutyric acid + NADPH + Hydrogen Ion details
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
2,5-Dioxopentanoate + NADP + Water unknown Oxoglutaric acid + NADPH + Hydrogen Ion details
Acetaldehyde + NADP + Water unknown Acetic acid + NADPH + Hydrogen Ion details
4-Aminobutyraldehyde + NADP + Water unknown Gamma-Aminobutyric acid + NADPH + Hydrogen Ion details
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyrroline-5-carboxylate reductase 1, mitochondrial
Reactions:
L-Proline + NADP unknown 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Ion details
4-Hydroxyproline + NADP unknown Pyrroline hydroxycarboxylic acid + NADPH + Hydrogen Ion details
Gene Name: PYCR1
Uniprot ID: P32322 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyrroline-5-carboxylate reductase 2
Reactions:
L-Proline + NADP unknown 1-Pyrroline-5-carboxylic acid + NADPH + Hydrogen Ion details
4-Hydroxyproline + NADP unknown Pyrroline hydroxycarboxylic acid + NADPH + Hydrogen Ion details
Gene Name: PYCR2
Uniprot ID: Q96C36 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-xylulose reductase
Reactions:
D-Xylitol + NADP unknown L-Threo-2-pentulose + NADPH details
D-Xylitol + NADP unknown L-Threo-2-pentulose + NADPH + Hydrogen Ion details
Gene Name: DCXR
Uniprot ID: Q7Z4W1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate 1-dehydrogenase
Reactions:
Glucose 6-phosphate + NADP unknown 6-phospho-D-glucono-1,5-lactone + NADPH details
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: G6PD
Uniprot ID: P11413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GDH/6PGL endoplasmic bifunctional protein
Reactions:
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: H6PD
Uniprot ID: O95479 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C3
Reactions:
trans-1,2-Dihydrobenzene-1,2-diol + NADP unknown Pyrocatechol + NADPH details
(5Z,13E)-(15S)-9-alpha,11-alpha,15-trihydroxyprosta-5,13-dienoate + NADP unknown (5Z,13E)-(15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + NADPH details
Testosterone + NADP unknown Androstenedione + NADPH details
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion unknown Tetrahydrodeoxycorticosterone + NADP details
5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion unknown Allopregnanolone + NADP details
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion unknown 5alpha-Pregnane-3alpha,20alpha-diol + NADP details
Gene Name: AKR1C3
Uniprot ID: P42330 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C1
Reactions:
trans-1,2-Dihydrobenzene-1,2-diol + NADP unknown Pyrocatechol + NADPH details
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion unknown Tetrahydrodeoxycorticosterone + NADP details
5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion unknown Allopregnanolone + NADP details
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion unknown 5alpha-Pregnane-3alpha,20alpha-diol + NADP details
Gene Name: AKR1C1
Uniprot ID: Q04828 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C2
Reactions:
trans-1,2-Dihydrobenzene-1,2-diol + NADP unknown Pyrocatechol + NADPH details
5alpha-Dihydrodeoxycorticosterone + NADPH + Hydrogen Ion unknown Tetrahydrodeoxycorticosterone + NADP details
5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion unknown Allopregnanolone + NADP details
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion unknown 5alpha-Pregnane-3alpha,20alpha-diol + NADP details
Gene Name: AKR1C2
Uniprot ID: P52895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glyoxylate reductase/hydroxypyruvate reductase
Reactions:
Glycolic acid + NADP unknown Glyoxylic acid + NADPH details
Glycolic acid + NADP unknown Glyoxylic acid + NADPH + Hydrogen Ion details
Glyceric acid + NADP unknown Hydroxypyruvic acid + NADPH + Hydrogen Ion details
Gene Name: GRHPR
Uniprot ID: Q9UBQ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4A11
Reactions:
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 20-Hydroxyeicosatetraenoic acid + NADP + Water details
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion unknown 11,12-EpETrE + NADP + Water details
All-trans-retinoic acid + NADPH + Hydrogen Ion + Oxygen unknown all-trans-18-Hydroxyretinoic acid + NADP + Water details
Gene Name: CYP4A11
Uniprot ID: Q02928 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methionine synthase reductase
Reactions:
[methionine synthase]-methylcob(I)alamin + S-Adenosylhomocysteine + NADP unknown [methionine synthase]-cob(II)alamin + NADPH + S-Adenosylmethionine details
Gene Name: MTRR
Uniprot ID: Q9UBK8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sepiapterin reductase
Reactions:
Dihydrobiopterin + NADP unknown Sepiapterin + NADPH details
L-erythro-tetrahydrobiopterin + NADP unknown Dyspropterin + NADPH details
L-erythro-tetrahydrobiopterin + NADP unknown 6-Lactoyltetrahydropterin + NADPH + Hydrogen Ion details
6-Lactoyltetrahydropterin + NADP unknown Dyspropterin + NADPH + Hydrogen Ion details
Gene Name: SPR
Uniprot ID: P35270 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 2
Reactions:
Estradiol + NADP unknown Estrone + NADPH + Hydrogen Ion details
Estriol + NADP unknown 16b-Hydroxyestrone + NADPH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B2
Uniprot ID: P37059 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 8
Reactions:
Estradiol + NADP unknown Estrone + NADPH + Hydrogen Ion details
Estriol + NADP unknown 16b-Hydroxyestrone + NADPH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B8
Uniprot ID: Q92506 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase
Reactions:
trans-1,2-Dihydrobenzene-1,2-diol + NADP unknown Pyrocatechol + NADPH details
D-Xylose + NADP unknown D-Xylono-1,5-lactone + NADPH details
D-Xylose + NADP unknown D-Xylono-1,5-lactone + NADPH + Hydrogen Ion details
1,2-Dihydronaphthalene-1,2-diol + NADP unknown Naphthalene-1,2-diol + NADPH + Hydrogen Ion details
Gene Name: DHDH
Uniprot ID: Q9UQ10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA