Showing metabocard for 16a-Hydroxydehydroisoandrosterone (BMDB0000352)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:08 UTC
Update Date2020-04-22 15:03:06 UTC
BMDB IDBMDB0000352
Secondary Accession Numbers
  • BMDB00352
Metabolite Identification
Common Name16a-Hydroxydehydroisoandrosterone
Description16a-Hydroxydehydroisoandrosterone, also known as 3b,16a-dihydroxy-androst-5-en-17-one or 5-androstene-3beta,16alpha-diol-17-one, 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, 16a-hydroxydehydroisoandrosterone is considered to be a steroid lipid molecule. 16a-Hydroxydehydroisoandrosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
16alpha-HydroxydehydroisoandrosteroneChEBI
3beta,16alpha-Dihydroxy-androst-5-en-17-oneChEBI
5-Androstene-3beta,16alpha-diol-17-oneChEBI
16Α-hydroxydehydroisoandrosteroneGenerator
3b,16a-Dihydroxy-androst-5-en-17-oneGenerator
3Β,16α-dihydroxy-androst-5-en-17-oneGenerator
5-Androstene-3b,16a-diol-17-oneGenerator
5-Androstene-3β,16α-diol-17-oneGenerator
16 alpha-Hydroxy-dehydroepiandrosteroneHMDB
16-HydroxydehydroandrosteroneHMDB
16-HydroxydehydroepiandrosteroneHMDB
16a-Hydroxy-dheaHMDB
16a-HydroxydehydroandrosteroneHMDB
16a-HydroxydehydroepiandrosteroneHMDB
3b,16a-Dihydroxyandrost-5-en-17-oneHMDB
Androst-5-ene-3b-16a-diol-17-oneHMDB
16alpha-Hydroxy-dehydroepiandrosteroneHMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-oneHMDB
16 alpha-HydroxydehydroisoandrosteroneHMDB
3,16-Dihydroxyandrost-5-en-17-oneHMDB
3 beta,16 beta-Dihydroxyandrost-5-en-17-oneHMDB
16 beta-HydroxydehydroepiandrosteroneHMDB
3 beta,16 alpha-Dihydroxyandrost-5-en-17-oneHMDB
16-Hydroxydehydroepiandrosterone, (16beta)-isomerHMDB
16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomerHMDB
16Α-hydroxydehydroepiandrosteroneHMDB
16a-HydroxydehydroisoandrosteroneGenerator
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name16a-Hydroxy-DHEA
CAS Registry Number1232-73-1
SMILES
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
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/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1
InChI KeyQQIVKFZWLZJXJT-DNKQKWOHSA-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
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.42ALOGPS
logP2.49ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.15 m³·mol⁻¹ChemAxon
Polarizability34.85 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, Positivesplash10-01r2-0190000000-8f531134e0d23da25da5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1038900000-e6ab9b68f3f5cbbada20View 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 (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 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 (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0194000000-ebe887790f49b4681923View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0291000000-dd1067b167ad1b942053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pxr-3690000000-ff802ceebc639b3e7c1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-c31ccc892715a3b41570View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0079000000-ca33420930d851c47a69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-1090000000-e8a494aec5ecf04bc8fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0069000000-057040f4b3850a066367View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-0982000000-202e2a5dcedc0d7b97b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-1910000000-6544390a129e44d96106View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0039000000-af52444aa96638a90cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-1094000000-48ce674daa94d6aea6fbView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000352
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021975
KNApSAcK IDNot Available
Chemspider ID92168
KEGG Compound IDC05139
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5341
PubChem Compound102030
PDB IDNot Available
ChEBI ID27771
References
Synthesis ReferenceSiiter, Pentti K.; MacDonald, Paul C. Placental estrogen biosynthesis during human pregnancy. Journal of Clinical Endocrinology and Metabolism (1966), 26(7), 751-61.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available