Showing metabocard for Epiandrosterone (BMDB0000365)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:23 UTC
Update Date2020-05-11 18:23:19 UTC
BMDB IDBMDB0000365
Secondary Accession Numbers
  • BMDB00365
Metabolite Identification
Common NameEpiandrosterone
DescriptionEpiandrosterone 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. Based on a literature review a significant number of articles have been published on Epiandrosterone.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-EpiandrosteroneHMDB
3b-AndrosteroneHMDB
3b-Hydroxy-17-oxo-5a-androstaneHMDB
3b-Hydroxy-5a-androstan-17-oneHMDB
3b-Hydroxy-5a-androstane-17-oneHMDB
3b-Hydroxyandrostan-17-oneHMDB
3b-Hydroxyetioallocholan-17-oneHMDB
3b-OH-5a-Androstane-17-oneHMDB
5a-Androstan-3b-ol-17-oneHMDB
5a-Androstane-3b-ol-17-oneHMDB
D-EpiandrosteroneHMDB
Epi-andosteroneHMDB
Epi-androsteroneHMDB
Iso-androsteroneHMDB
IsoandrosteroneHMDB
trans-AndrosteroneHMDB
(3Β,5α)-3-hydroxyandrostan-17-oneHMDB
3Β-androsteroneHMDB
3Β-hydroxy-17-oxo-5α-androstaneHMDB
3Β-hydroxy-5α-androstan-17-oneHMDB
3Β-hydroxy-5α-androstane-17-oneHMDB
3Β-hydroxyandrostan-17-oneHMDB
3Β-hydroxyetioallocholan-17-oneHMDB
3Β-OH-5α-androstane-17-oneHMDB
5Α-androstan-17-one-3β-olHMDB
5Α-androstan-3β-ol-17-oneHMDB
5Α-androstane-3β-ol-17-oneHMDB
(3beta,5alpha)-3-Hydroxyandrostan-17-oneHMDB
3beta-AndrosteroneHMDB
3beta-Hydroxy-17-oxo-5alpha-androstaneHMDB
3beta-Hydroxy-5alpha-androstan-17-oneHMDB
3beta-Hydroxy-5alpha-androstane-17-oneHMDB
3beta-Hydroxyandrostan-17-oneHMDB
3beta-Hydroxyetioallocholan-17-oneHMDB
3beta-OH-5alpha-Androstane-17-oneHMDB
5alpha-Androstan-17-one-3beta-olHMDB
5alpha-Androstan-3beta-ol-17-oneHMDB
5alpha-Androstane-3beta-ol-17-oneHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number481-29-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1
InChI KeyQGXBDMJGAMFCBF-QRIARFFBSA-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
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0202 mg/mL at 23 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0f7k-1139000000-2bff067a4137502d6ea7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0190000000-b665b61b3fc9060b35b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4900000000-e43c3bdb0c139ec15f8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9300000000-c77bd97ae174005bf348View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-fb385ad40b5d4ae1a6d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0290000000-6287ec557af150ef07feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-3690000000-da6f3211b1e397dcf1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-03f14a475acfab5558d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5e4902f7af7820145954View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xx-2090000000-97cca29f0df7b3cc3714View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-afb176951034ef62419fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052e-0930000000-1ed776267953f7acda8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2900000000-1ba60805778f2942bfd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-00c0e7de4e528b98df5cView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000365
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021984
KNApSAcK IDNot Available
Chemspider ID9230560
KEGG Compound IDC07635
BioCyc IDNot Available
BiGG ID45201
Wikipedia LinkEpiandrosterone
METLIN IDNot Available
PubChem Compound11055399
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceJohnson, Wm. S.; Bannister, Brian; Pappo, Raphael. Steroid total synthesis-hydrochrysene approach. VII. Metal-in-ammonia reduction of the aromatic nucleus. dl-Epiandrosterone and the lumi epimer. Journal of the American Chemical Society (1956), 78 6331-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available