Showing metabocard for 11b-Hydroxyandrost-4-ene-3,17-dione (BMDB0006773)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:55 UTC
Update Date2020-05-07 14:45:06 UTC
MCDB ID BMDB0006773
Secondary Accession Numbers
  • BMDB06773
Metabolite Identification
Common Name11b-Hydroxyandrost-4-ene-3,17-dione
Description11b-Hydroxyandrost-4-ene-3,17-dione is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 11b-Hydroxyandrost-4-ene-3,17-dione participates in a number of enzymatic reactions, within cattle. In particular, 11b-Hydroxyandrost-4-ene-3,17-dione can be biosynthesized from androstenedione; which is mediated by the enzyme cytochrome P450 11B1. In addition, 11b-Hydroxyandrost-4-ene-3,17-dione can be converted into adrenosterone; which is catalyzed by the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In cattle, 11b-hydroxyandrost-4-ene-3,17-dione is involved in the metabolic pathway called the androstenedione metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11 beta-HydroxyandrostenedioneMeSH
11-Hydroxy-4-androstene-3,17-dioneMeSH
11-Hydroxyandrostenedione, (11beta)-isomerMeSH
11-Hydroxyandrostenedione, (11alpha)-isomerMeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11alpha)-isomerMeSH
11-Hydroxyandrostenedione, (9beta,10alpha,11beta)-isomerMeSH
Chemical FormulaC19H26O3
Average Molecular Weight302.414
Monoisotopic Molecular Weight302.188194697
IUPAC Name(1S,2R,10S,11S,15S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional Name(1S,2R,10S,11S,15S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O3/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/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15?,17+,18-,19-/m0/s1
InChI KeyWSCUHXPGYUMQEX-CRIVMUBDSA-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
  • 11-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2ALOGPS
logP2.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.88ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.2 m³·mol⁻¹ChemAxon
Polarizability34.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c00-0690000000-fdef84fb9f873beec4932018-04-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0094000000-056565c94e82d149c42b2018-04-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kw0-0190000000-2cc4873310eff92870322018-04-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0553-3390000000-a6f85689c2880fe5404b2018-04-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-4dba45b5e06401595fb42018-04-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-cf44b11813cdb2dd6a4d2018-04-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2090000000-8efa9e28fb744da40fe82018-04-06View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0154970
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108106
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]