Showing metabocard for 3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al (BMDB0006753)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:32 UTC
Update Date2020-04-22 15:18:26 UTC
BMDB IDBMDB0006753
Secondary Accession Numbers
  • BMDB06753
Metabolite Identification
Common Name3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al
Description3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. 3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al can be biosynthesized from 11b,21-dihydroxy-3,20-oxo-5b-pregnan-18-al; which is mediated by the enzyme aldo-keto reductase family 1 member C4. In cattle, 3a,11b,21-trihydroxy-20-oxo-5b-pregnan-18-al is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-alHMDB
Chemical FormulaC21H32O5
Average Molecular Weight364.4758
Monoisotopic Molecular Weight364.224974134
IUPAC Name(5R)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde
Traditional Name(5R)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC12CC[C@@H](O)CC1CCC1C3CCC(C(=O)CO)C3(CC(O)C21)C=O
InChI Identifier
InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h11-17,19,22,24-25H,2-10H2,1H3/t12?,13-,14?,15?,16?,17?,19?,20?,21?/m1/s1
InChI KeyYWTDWORQGPLRLL-NDCWLUSSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 18-oxosteroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 11-hydroxysteroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aldehyde
  • Primary 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
  • 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
logP1.69ALOGPS
logP0.89ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.99 m³·mol⁻¹ChemAxon
Polarizability40.45 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, Positivesplash10-001s-0319000000-cbab8674e6351e8fa042View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1010390000-69f51640095eeadde81cView 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0009000000-c1bce2add0ff441b02afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-0119000000-8f8e51f57f94947fb175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4297000000-c65747d417176b5c039aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-02d44db33264740a8017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07cb-1009000000-30c142d96cd09c673dbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-7098000000-8bcc5760748cc6a69e42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009000000-8aa991da4308c913a58aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0019000000-0a114e28eed8d64ca170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9632000000-180377320cc9ca9eff3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-a1a10f1bf996d8bb218bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8029000000-0ff6b9f8429157a98e86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06u6-4059000000-8732aabd6ff373484e61View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006753
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024057
KNApSAcK IDNot Available
Chemspider ID389571
KEGG Compound IDC05474
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440695
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available