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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:07 UTC
HMDB IDHMDB0000899
Secondary Accession Numbers
  • HMDB0011608
  • HMDB00899
  • HMDB11608
Metabolite Identification
Common NameAndrostanedione
DescriptionAndrostanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1582752163
Synonyms
ValueSource
5alpha-Androstan-3,17-dioneChEBI
5a-Androstan-3,17-dioneGenerator
5Α-androstan-3,17-dioneGenerator
(5a)-Androstane-3,17-dioneHMDB
5-alpha-Androstane-3,17-dioneHMDB
5a-Androsta-3,17-dioneHMDB
5a-Androstane-3, 17-dioneHMDB
5a-Androstane-3,17-dioneHMDB
5a-AndrostanedioneHMDB
5alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dioneHMDB
Androstane-3,7-dioneHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomerHMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomerHMDB
Androstane-3,17-dione, (5beta)-isomerHMDB
3,17-Dioxy-5 alpha-androstaneHMDB
5 alpha-AndrostanedioneHMDB
5 beta-Androstane-3,17-dioneHMDB
5 alpha-Androstane-3,17-dioneHMDB
Androstane-3,17-dione, (5alpha)-isomerHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
Traditional Name(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione
CAS Registry Number846-46-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1
InChI KeyRAJWOBJTTGJROA-WZNAKSSCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133.5 - 134.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available174.32http://allccs.zhulab.cn/database/detail?ID=AllCCS00000226
[M+H]+Not Available180.954http://allccs.zhulab.cn/database/detail?ID=AllCCS00000226
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0074 g/LALOGPS
logP3.4ALOGPS
logP3.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.78 m³·mol⁻¹ChemAxon
Polarizability33.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.31231661259
DarkChem[M-H]-169.59131661259
AllCCS[M+H]+173.46332859911
AllCCS[M-H]-178.83832859911
DeepCCS[M-2H]-205.49830932474
DeepCCS[M+Na]+180.51930932474
AllCCS[M+H]+173.532859911
AllCCS[M+H-H2O]+170.432859911
AllCCS[M+NH4]+176.332859911
AllCCS[M+Na]+177.132859911
AllCCS[M-H]-178.832859911
AllCCS[M+Na-2H]-178.932859911
AllCCS[M+HCOO]-179.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Androstanedione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2613.0Standard polar33892256
Androstanedione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2432.3Standard non polar33892256
Androstanedione[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2629.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Androstanedione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2620.6Semi standard non polar33892256
Androstanedione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2459.1Standard non polar33892256
Androstanedione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2889.7Standard polar33892256
Androstanedione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2604.5Semi standard non polar33892256
Androstanedione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2496.8Standard non polar33892256
Androstanedione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O2991.4Standard polar33892256
Androstanedione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2583.4Semi standard non polar33892256
Androstanedione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2503.5Standard non polar33892256
Androstanedione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2988.7Standard polar33892256
Androstanedione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2648.3Semi standard non polar33892256
Androstanedione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2546.7Standard non polar33892256
Androstanedione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2957.8Standard polar33892256
Androstanedione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2656.3Semi standard non polar33892256
Androstanedione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2569.7Standard non polar33892256
Androstanedione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2956.9Standard polar33892256
Androstanedione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2859.5Semi standard non polar33892256
Androstanedione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C2604.0Standard non polar33892256
Androstanedione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3050.2Standard polar33892256
Androstanedione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12839.6Semi standard non polar33892256
Androstanedione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12711.8Standard non polar33892256
Androstanedione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13150.9Standard polar33892256
Androstanedione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12804.1Semi standard non polar33892256
Androstanedione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12728.5Standard non polar33892256
Androstanedione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13149.1Standard polar33892256
Androstanedione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13174.0Semi standard non polar33892256
Androstanedione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C12806.4Standard non polar33892256
Androstanedione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13199.0Standard polar33892256
Androstanedione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13171.0Semi standard non polar33892256
Androstanedione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC12825.3Standard non polar33892256
Androstanedione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC=C(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13199.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Androstanedione GC-MS (Non-derivatized)splash10-003u-9711000000-845e34a01c44999f2ded2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Androstanedione EI-B (Non-derivatized)splash10-000i-2790000000-3265da77fd4cc7bfa1c92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Androstanedione GC-MS (Non-derivatized)splash10-003u-9711000000-845e34a01c44999f2ded2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0490000000-e4819053bc47c4809a6c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0090000000-decf354145d0bc46e6242012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-01vk-4910000000-1f05b00fe5f61dd134c32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05ng-9800000000-ef0555e1d54150aaffd22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Linear Ion Trap , negative-QTOFsplash10-0aou-0290000000-ffd1b454b311f471cb732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Linear Ion Trap , positive-QTOFsplash10-014i-0390000000-f4995b2047bec58846f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androstanedione Linear Ion Trap , positive-QTOFsplash10-00di-0390000000-a4cf943964aae2cffee62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 10V, Positive-QTOFsplash10-000i-0190000000-8b26abdeab6d06d616e32017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 20V, Positive-QTOFsplash10-05a9-0490000000-5411cf1f548c371b71f52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 40V, Positive-QTOFsplash10-0mkg-2690000000-fd3043c5fcf860949b792017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 10V, Negative-QTOFsplash10-000i-0090000000-be391ca3b57229eb2b282017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 20V, Negative-QTOFsplash10-000i-0090000000-0c9ee67f63fb1f48c00a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 40V, Negative-QTOFsplash10-052f-3190000000-4d4ec5ab2ebbcfdebbd02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 10V, Positive-QTOFsplash10-000i-0090000000-a3a5ee5e1cdb4d550aac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 20V, Positive-QTOFsplash10-0h90-0970000000-66d8653b98d2df4aa3272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 40V, Positive-QTOFsplash10-0a4i-1900000000-2a46c86775b66edae0182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 10V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 20V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanedione 40V, Negative-QTOFsplash10-0f79-0090000000-0497207bd4a67a50d8d82021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
Tissue Locations
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00036 (0.00020-0.00070) uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01561
Phenol Explorer Compound IDNot Available
FooDB IDFDB022307
KNApSAcK IDNot Available
Chemspider ID193520
KEGG Compound IDC00674
BioCyc IDCPD-342
BiGG ID42505
Wikipedia LinkAndrostanedione
METLIN ID5855
PubChem Compound222865
PDB IDNot Available
ChEBI ID15994
Food Biomarker OntologyNot Available
VMH IDANDRSTANDN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMarker, Russell E.; Kamm, Oliver; Jones, David M.; Oakwood, Thomas S. Sterols. VIII. Preparation of androstanedione from allopregnanediol. Journal of the American Chemical Society (1937), 59 614-16.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
  2. Gonzalez-Santos MR, Gaja-Rodriguez OV, Alonso-Uriarte R, Sojo-Aranda I, Cortes-Gallegos V: Sleep deprivation and adaptive hormonal responses of healthy men. Arch Androl. 1989;22(3):203-7. [PubMed:2757458 ]

Enzymes

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
Androsterone + NAD → Androstanedione + NADH + Hydrogen Iondetails
Androsterone + NADP → Androstanedione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A2
Uniprot ID:
P31213
Molecular weight:
28407.035
Reactions
Androstanedione + Acceptor → Androstenedione + Reduced acceptordetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
Reactions
Androstanedione + Acceptor → Androstenedione + Reduced acceptordetails
General function:
Involved in oxidoreductase activity, acting on the CH-CH group of donors
Specific function:
Plays a key role in early steps of protein N-linked glycosylation by being required for the conversion of polyprenol into dolichol. Dolichols are required for the synthesis of dolichol-linked monosaccharides and the oligosaccharide precursor used for N-glycosylation. Acts as a polyprenol reductase that promotes the reduction of the alpha-isoprene unit of polyprenols into dolichols in a NADP-dependent mechanism. Also able to convert testosterone (T) into 5-alpha-dihydrotestosterone (DHT).
Gene Name:
SRD5A3
Uniprot ID:
Q9H8P0
Molecular weight:
36521.005
Reactions
Androstanedione + Acceptor → Androstenedione + Reduced acceptordetails