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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 09:17:15 UTC
Update Date2022-09-22 18:34:17 UTC
HMDB IDHMDB0004025
Secondary Accession Numbers
  • HMDB0005943
  • HMDB04025
  • HMDB05943
Metabolite Identification
Common NamePregnanediol
Description
Structure
Thumb
Synonyms
ValueSource
5beta-Pregnane-3alpha,20alpha-diolKegg
PregnandiolKegg
DiolKegg
5b-Pregnane-3a,20a-diolGenerator
5Β-pregnane-3α,20α-diolGenerator
(3alpha,5beta,20S)-Pregnane-3,20-diolHMDB
(3Α,5β,20S)-pregnane-3,20-diolHMDB
3alpha,20alpha-Dihydroxy-5beta-pregnaneHMDB
3Α,20α-dihydroxy-5β-pregnaneHMDB
5beta-PregnanediolHMDB
5Β-pregnanediolHMDB
PregnanediolHMDB
Chemical FormulaC21H36O2
Average Molecular Weight320.517
Monoisotopic Molecular Weight320.271530399
IUPAC Name(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol
Traditional Name(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol
CAS Registry Number80-92-2
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O
InChI Identifier
InChI=1S/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyYWYQTGBBEZQBGO-BERLURQNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point243.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.12 (0.032-0.21) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.25 (0.046-0.46) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023280
KNApSAcK IDNot Available
Chemspider ID190585
KEGG Compound IDC05484
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPregnanediol
METLIN IDNot Available
PubChem Compound219833
PDB IDNot Available
ChEBI ID8387
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referencetoh, Shinji; Ichikawa, Harumi; Takagi, Hidetoshi; Yoshizawa, Itsuo. Clinical analysis on steroids. XLII. On the rearrangement reactions of pregnanediol disulfate to D13-steroid, and its 20-isomeric sulfate to D-homosteroids. Chemical & Pharmaceutical Bull
Material Safety Data Sheet (MSDS)Not Available
General References