Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:24 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0002984
Secondary Accession Numbers
  • HMDB02984
Metabolite Identification
Common Name11-Hydroxyandrosterone
Description11-Hydroxyandrosterone 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, 11-hydroxyandrosterone is considered to be a steroid. Based on a literature review a significant number of articles have been published on 11-Hydroxyandrosterone.
Structure
Data?1582752260
Synonyms
ValueSource
11beta-HydroxyandrosteroneKegg
11b-HydroxyandrosteroneGenerator
11Β-hydroxyandrosteroneGenerator
11-beta-HydroxyandrosteroneHMDB
11-Hydroxy-androsteroneHMDB
11-HydroxyetiocholanoloneHMDB, MeSH
11beta-Hydroxy-androsteroneHMDB
11 beta-HydroxyandrosteroneMeSH, HMDB
11 beta-Hydroxyandrosterone, (3alpha,5alpha)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3alpha,5alpha,11alpha)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta,11alpha)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3alpha,5beta,11beta)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3beta,5alpha,11beta)-isomerMeSH, HMDB
11 beta-Hydroxyandrosterone, (3beta,5beta,11beta)-isomerMeSH, HMDB
11 beta-HydroxyetiocholanoloneMeSH, HMDB
3alpha,11beta-Dihydroxy-5beta-androstan-17-oneMeSH, HMDB
Chemical FormulaC19H30O3
Average Molecular Weight306.4397
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2S,5R,7S,10S,11S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
Traditional Name11-hydroxyandrosterone
CAS Registry Number57-61-4
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13-,14-,15-,17+,18-,19-/m0/s1
InChI KeyPIXFHVWJOVNKQK-PTXZMSDUSA-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-hydroxysteroid
  • Hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility251.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.4ALOGPS
logP2.46ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.89ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.4 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.46931661259
DarkChem[M-H]-168.39431661259
DeepCCS[M-2H]-210.46530932474
DeepCCS[M+Na]+184.89930932474
AllCCS[M+H]+178.832859911
AllCCS[M+H-H2O]+175.932859911
AllCCS[M+NH4]+181.632859911
AllCCS[M+Na]+182.432859911
AllCCS[M-H]-180.932859911
AllCCS[M+Na-2H]-181.132859911
AllCCS[M+HCOO]-181.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-Hydroxyandrosterone[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2610.2Standard polar33892256
11-Hydroxyandrosterone[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2662.9Standard non polar33892256
11-Hydroxyandrosterone[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2866.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11-Hydroxyandrosterone,1TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CCC2=O2694.7Semi standard non polar33892256
11-Hydroxyandrosterone,1TMS,isomer #2C[C@]12C[C@H](O)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2723.4Semi standard non polar33892256
11-Hydroxyandrosterone,1TMS,isomer #3C[C@]12C[C@H](O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2724.5Semi standard non polar33892256
11-Hydroxyandrosterone,2TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2645.3Semi standard non polar33892256
11-Hydroxyandrosterone,2TMS,isomer #2C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2631.9Semi standard non polar33892256
11-Hydroxyandrosterone,2TMS,isomer #3C[C@]12C[C@H](O)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2714.0Semi standard non polar33892256
11-Hydroxyandrosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2622.8Semi standard non polar33892256
11-Hydroxyandrosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2712.2Standard non polar33892256
11-Hydroxyandrosterone,3TMS,isomer #1C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3013.1Standard polar33892256
11-Hydroxyandrosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@]2(C)C(=O)CC[C@H]2[C@@H]2CC[C@H]3C[C@H](O)CC[C@]3(C)[C@@H]122949.4Semi standard non polar33892256
11-Hydroxyandrosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)C[C@H](O)[C@@H]32)C12988.4Semi standard non polar33892256
11-Hydroxyandrosterone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C2994.2Semi standard non polar33892256
11-Hydroxyandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@]2(C)C(=O)CC[C@H]2[C@@H]2CC[C@H]3C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@@H]123134.7Semi standard non polar33892256
11-Hydroxyandrosterone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C3116.4Semi standard non polar33892256
11-Hydroxyandrosterone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C3223.9Semi standard non polar33892256
11-Hydroxyandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C3298.3Semi standard non polar33892256
11-Hydroxyandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C3101.8Standard non polar33892256
11-Hydroxyandrosterone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C3322.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxyandrosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fs-0490000000-845f1333bf38189468d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxyandrosterone GC-MS (2 TMS) - 70eV, Positivesplash10-0019-1646900000-5f3db467d73d551ea5232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11-Hydroxyandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 10V, Positive-QTOFsplash10-052r-0092000000-7ee9333f2ca834b6dc412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 20V, Positive-QTOFsplash10-059i-0190000000-ce3d130e38421477defc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 40V, Positive-QTOFsplash10-0a6r-4290000000-29cdb28119cfafcfeccc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 10V, Negative-QTOFsplash10-0a4i-0049000000-0583782d3fbeec16854d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 20V, Negative-QTOFsplash10-0a4r-0097000000-81d91167799b4dbad7ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 40V, Negative-QTOFsplash10-01rf-3090000000-758543fa8bec7808bdcf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 10V, Negative-QTOFsplash10-0a4i-0009000000-a47a32e502bdb7f0b4482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 20V, Negative-QTOFsplash10-0a4i-0019000000-1134d785f6f919e12d2b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 40V, Negative-QTOFsplash10-0udi-2059000000-3ef680fe7da1ffe71ae22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 10V, Positive-QTOFsplash10-0a4r-0079000000-01b6a8fdd7a9d5002e492021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 20V, Positive-QTOFsplash10-0002-3982000000-977ebfec91fc6f4060f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11-Hydroxyandrosterone 40V, Positive-QTOFsplash10-014j-3920000000-7d1d2e192fc64a2e28fb2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Ovary
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.15 (0.11-0.15) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.069 (0.047-0.088) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.000073 +/- 0.000028 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00013 +/- 0.000093 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023089
KNApSAcK IDNot Available
Chemspider ID8461834
KEGG Compound IDC14606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3178
PubChem Compound10286365
PDB IDNot Available
ChEBI ID34350
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1157181
References
Synthesis ReferenceKlyne, W.; Ridley, Sheila. Urinary steroids and related compounds. I. 11-Substituted derivatives of androsterone. Journal of the Chemical Society (1956), 4825-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Akgun S, Ertel NH, Imperato-McGinley J, Sayli BS, Shackleton C: Familial male pseudohermaphroditism due to 5-alpha-reductase deficiency in a Turkish village. Am J Med. 1986 Aug;81(2):267-74. [PubMed:3740084 ]
  2. Pucsok JM, Gyore I, Hollosi I, Soos E, Ali Ghasemi NR, Frenkl R: Urine steroid profile of judo competitors affected by acute physical exercises. J Chromatogr Sci. 2005 Sep;43(8):438-40. [PubMed:16212787 ]
  3. Ball KD, Levell MJ, Pickup ME: The effect of ibuprofen on the excretion of steroid metabolites. Clin Chim Acta. 1982 Sep 1;124(1):23-9. [PubMed:7127837 ]
  4. Norli HR, Esbensen K, Westad F, Birkeland KI, Hemmersbach P: Chemometric evaluation of urinary steroid profiles in doping control. J Steroid Biochem Mol Biol. 1995 Jul;54(1-2):83-8. [PubMed:7632620 ]
  5. Vierhapper H, Nowotny P, Waldhausl W: Stimulation of gonadal steroid synthesis by chronic excess of adrenocorticotropin in patients with adrenocortical insufficiency. J Clin Invest. 1986 Apr;77(4):1063-70. [PubMed:3007576 ]