Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000322
Secondary Accession Numbers
  • HMDB00322
Metabolite Identification
Common Name16-Oxoandrostenediol
Description16-Oxoandrostenediol is a naturally occurring androgenic steroid hormone generated by the adrenal glands. It has been found in the urine of newborn infants. Secretion of this steroid is suppressed by dexamethasone. Levels of this hormone are almost absent by 5 months of age. ((Steroids (1964), 3(1), 77-83.) ). 16-Oxoandrostenediol is a natural hormone with androgenic activity and that two potent antiandrogens: hydroxyflutamide (Eulexin) and bicalutamide (Casodex).
Structure
Data?1582752123
Synonyms
ValueSource
(3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3b,17b-Dihydroxy-androst-5-en-16-oneHMDB
3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3beta,17beta-Dihydroxy-androst-5-en-16-oneHMDB
5-Androsten-3b,17b-diol-16-oneHMDB
Androst-5-ene-3b,17b-diol-16-oneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one
Traditional Name5-androsten-3b,17b-diol-16-one
CAS Registry Number1159-66-6
SMILES
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O
InChI Identifier
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1
InChI KeyAKRBLZKRYPEVIK-IACDPKRHSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 16-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.39ALOGPS
logP2.13ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.95 m³·mol⁻¹ChemAxon
Polarizability34.66 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]+169.05431661259
DarkChem[M-H]-165.55931661259
AllCCS[M+H]+177.88732859911
AllCCS[M-H]-180.55932859911
DeepCCS[M-2H]-209.3930932474
DeepCCS[M+Na]+184.61830932474
AllCCS[M+H]+177.932859911
AllCCS[M+H-H2O]+174.932859911
AllCCS[M+NH4]+180.732859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-180.632859911
AllCCS[M+Na-2H]-180.732859911
AllCCS[M+HCOO]-180.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16-OxoandrostenediolC[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O2822.0Standard polar33892256
16-OxoandrostenediolC[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O2636.0Standard non polar33892256
16-OxoandrostenediolC[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O2701.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-Oxoandrostenediol,1TMS,isomer #1C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(=O)[C@@H]2O2797.5Semi standard non polar33892256
16-Oxoandrostenediol,1TMS,isomer #2C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(=O)[C@@H]2O[Si](C)(C)C2835.0Semi standard non polar33892256
16-Oxoandrostenediol,1TMS,isomer #3C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O2759.1Semi standard non polar33892256
16-Oxoandrostenediol,1TMS,isomer #4C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O2723.2Semi standard non polar33892256
16-Oxoandrostenediol,2TMS,isomer #1C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(=O)[C@@H]2O[Si](C)(C)C2842.5Semi standard non polar33892256
16-Oxoandrostenediol,2TMS,isomer #2C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O2755.8Semi standard non polar33892256
16-Oxoandrostenediol,2TMS,isomer #3C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O2731.2Semi standard non polar33892256
16-Oxoandrostenediol,2TMS,isomer #4C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2821.3Semi standard non polar33892256
16-Oxoandrostenediol,2TMS,isomer #5C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C2793.6Semi standard non polar33892256
16-Oxoandrostenediol,3TMS,isomer #1C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2800.2Semi standard non polar33892256
16-Oxoandrostenediol,3TMS,isomer #1C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2783.4Standard non polar33892256
16-Oxoandrostenediol,3TMS,isomer #1C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3101.4Standard polar33892256
16-Oxoandrostenediol,3TMS,isomer #2C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C2781.5Semi standard non polar33892256
16-Oxoandrostenediol,3TMS,isomer #2C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C2776.6Standard non polar33892256
16-Oxoandrostenediol,3TMS,isomer #2C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C3082.4Standard polar33892256
16-Oxoandrostenediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CCC3C4CC(=O)[C@H](O)[C@@]4(C)CCC32)C13063.8Semi standard non polar33892256
16-Oxoandrostenediol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C(=O)CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C3103.4Semi standard non polar33892256
16-Oxoandrostenediol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)[C@@]2(C)CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C2C13027.4Semi standard non polar33892256
16-Oxoandrostenediol,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O3010.5Semi standard non polar33892256
16-Oxoandrostenediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CCC3C4CC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC32)C13339.2Semi standard non polar33892256
16-Oxoandrostenediol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C13243.7Semi standard non polar33892256
16-Oxoandrostenediol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O3225.6Semi standard non polar33892256
16-Oxoandrostenediol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C2C13352.1Semi standard non polar33892256
16-Oxoandrostenediol,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3322.2Semi standard non polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C13490.8Semi standard non polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C13381.6Standard non polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C13388.2Standard polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3482.2Semi standard non polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3300.3Standard non polar33892256
16-Oxoandrostenediol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3373.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0190000000-9cdf4c9cbef99114d1a62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1124900000-4fffa382f7bdac19a2802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Oxoandrostenediol GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 10V, Positive-QTOFsplash10-052r-0094000000-bc00afb765c32f27cdb52015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 20V, Positive-QTOFsplash10-0a4r-0191000000-05d2e664ac4d9ef4363c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 40V, Positive-QTOFsplash10-0pvi-3590000000-c0b23f4d56161a2287912015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 10V, Negative-QTOFsplash10-0udi-0029000000-1cc7a9092823445c7d7e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 20V, Negative-QTOFsplash10-0udi-0079000000-0648fbf68146b515254a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 40V, Negative-QTOFsplash10-0076-2090000000-98800c5259e32862774e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 10V, Positive-QTOFsplash10-0a4r-0089000000-c34c64c1bec8748efad52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 20V, Positive-QTOFsplash10-07bk-0691000000-d7755077857648dfe7512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 40V, Positive-QTOFsplash10-07bg-7920000000-9ef2401b947b7cb415c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 20V, Negative-QTOFsplash10-0udi-0029000000-b27ed9406108417648cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Oxoandrostenediol 40V, Negative-QTOFsplash10-0udi-0295000000-ec640a8c6ea56960081a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • Adrenal Gland
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021948
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5311
PubChem Compound53477682
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu. Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives. Chemical & Pharmaceutical Bulletin (1964), 12(7), 808-12.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available