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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 IDHMDB0000217
Secondary Accession Numbers
  • HMDB00217
Metabolite Identification
Common NameNADP
DescriptionNicotinamide 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
Codehydrase IIChEBI
Codehydrogenase IIChEBI
Coenzyme IIChEBI
NAD phosphateChEBI
NADP nicotinamide-adenine-dinucleotide phosphATEChEBI
TPNChEBI
Triphosphopyridine nucleotideChEBI
NAD phosphoric acidGenerator
NADP nicotinamide-adenine-dinucleotide phosphoric acidGenerator
Dinucleotide phosphate, nicotinamide-adenineHMDB
NADPHHMDB
Nicotinamide-adenine dinucleotide phosphateHMDB
Nicotinamide adenine dinucleotide phosphateHMDB
Nucleotide, triphosphopyridineHMDB
Phosphate, nicotinamide-adenine dinucleotideHMDB
Adenine-nicotinamide dinucleotide phosphateHMDB
NADP+HMDB
beta-NADPHMDB
beta-Nicotinamide adenine dinucleotide phosphateHMDB
beta-TPNHMDB
Β-nadpHMDB
Β-nicotinamide adenine dinucleotide phosphateHMDB
Β-TPNHMDB
NADPChEBI, MeSH
Chemical FormulaC21H28N7O17P3
Average Molecular Weight743.405
Monoisotopic Molecular Weight743.075452041
IUPAC Name1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
Traditional Name1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
CAS Registry Number53-59-8
SMILES
NC(=O)C1=C[N+](=CC=C1)[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/C21H28N7O17P3/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/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyXJLXINKUBYWONI-NNYOXOHSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility4.15 g/LALOGPS
logP-0.81ALOGPS
logP-10ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area367.62 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity151.75 m³·mol⁻¹ChemAxon
Polarizability62.46 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]+212.530932474
DeepCCS[M-H]-210.65430932474
DeepCCS[M-2H]-244.68630932474
DeepCCS[M+Na]+218.64830932474
AllCCS[M+H]+237.932859911
AllCCS[M+H-H2O]+237.632859911
AllCCS[M+NH4]+238.132859911
AllCCS[M+Na]+238.132859911
AllCCS[M-H]-225.432859911
AllCCS[M+Na-2H]-227.232859911
AllCCS[M+HCOO]-229.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NADPNC(=O)C1=C[N+](=CC=C1)[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]1O5700.9Standard polar33892256
NADPNC(=O)C1=C[N+](=CC=C1)[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]1O3992.4Standard non polar33892256
NADPNC(=O)C1=C[N+](=CC=C1)[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]1O6237.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NADP GC-MS (TMS_2_18) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0219003700-2f52e3c5db41066a112c2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0uk9-0301009000-a3d0c464e56f6e320c802019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0000090000-c18a7719161c63a719382019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0udi-0000009000-1dde5b221786fe3753042019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00dl-0209000700-02057593d6470f6a20752019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0uk9-0301109000-bf4996084c09a91764892019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0uk9-0301009000-b3e8d304dfdc4711e0ce2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0udi-0000009000-384d275a638928dd40f12019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00dl-0000229600-bd164bae0cc54f45b9612019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-004i-0027900000-25e0180b7638ed18e2072019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0011953000-c328377f842fac60b55e2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0000009000-0ec3670e706b086d382a2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00dl-0000109700-df2a731fd5f55e9e7a8e2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-0a4i-0011953000-981d13d6b50f18ebc9102019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0000009000-f9526262833104be0a2e2019-11-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - NADP LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0000009000-c0cedd489befb20733702019-11-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 10V, Positive-QTOFsplash10-0006-0000000900-d510a9264bee14bd85ee2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 20V, Positive-QTOFsplash10-000t-0000000900-fb29571fb864b5c4179b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 40V, Positive-QTOFsplash10-006y-2910001000-5066541857e9b5d8bbbf2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 10V, Negative-QTOFsplash10-0006-1000000900-8cdcef7ab2fa3bdd51e12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 20V, Negative-QTOFsplash10-0007-6100000900-396416b5dd4d0892e43d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 40V, Negative-QTOFsplash10-005a-9100000000-e5765145791ae2971a892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 10V, Positive-QTOFsplash10-000i-0900001200-ff4ca74a6b585e3592752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 20V, Positive-QTOFsplash10-000i-0901113400-26884ea59b81b65812752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NADP 40V, Positive-QTOFsplash10-000j-2902210000-acc59733c27dab4bbf952021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2019-11-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
  • Peroxisome
Biospecimen Locations
  • Blood
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified19.6 (18.3 - 20.8) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified24.4 (21.5 - 27.4) uMAdult (>18 years old)BothPellagra details
Associated Disorders and Diseases
Disease References
Pellagra
  1. Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]
Associated OMIM IDsNone
DrugBank IDDB03461
Phenol Explorer Compound IDNot Available
FooDB IDFDB021908
KNApSAcK IDNot Available
Chemspider ID5674
KEGG Compound IDC00006
BioCyc IDNADP
BiGG IDNot Available
Wikipedia LinkNicotinamide adenine dinucleotide phosphate
METLIN IDNot Available
PubChem Compound5885
PDB IDNot Available
ChEBI ID44409
Food Biomarker OntologyNot Available
VMH IDNADP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSimon, L. M.; Kotorman, M.; Szajani, B. Coenzyme production using immobilized enzymes. I. Preparation, characterization, and laboratory-scale application of an immobilized NAD+ kinase. Enzyme and Microbial Technology (1992), 14(12), 997-1000.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Siddique YH, Beg T, Afzal M: Genotoxic potential of ethinylestradiol in cultured mammalian cells. Chem Biol Interact. 2005 Jan 15;151(2):133-41. [PubMed:15698584 ]
  2. Himmelstein MW, Carpenter SC, Hinderliter PM, Snow TA, Valentine R: The metabolism of beta-chloroprene: preliminary in-vitro studies using liver microsomes. Chem Biol Interact. 2001 Jun 1;135-136:267-84. [PubMed:11397396 ]

Only showing the first 10 proteins. There are 207 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 207 proteins in total.