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Human Metabolome Database Version 3.5

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Showing metabocard for 3a,7a-Dihydroxy-5b-cholestanate (HMDB03851)

Record Information
Version 3.5
Creation Date 2006-08-12 23:59:12 -0600
Update Date 2013-02-08 17:12:47 -0700
HMDB ID HMDB03851
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,7a-Dihydroxy-5b-cholestanate
Description 20 alpha-dihydroxyprogesterone is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. It is known that 20 alpha-dihydroxyprogesterone is increased at midcycle but its importance in regulating LH has not been studied. Howevever periovulatory levels of 20 alpha-dihydroxyprogesterone do not play a role in modulating the estrogen-induced bioactive LH surge. (PMID:2245841 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 17,20a-Dihydroxy-4-pregnen-3-one
  2. 17,20a-Dihydroxy-Pregn-4-en-3-one
  3. 17a,20a-Dihydroxy-4-pregnen-3-one
  4. 17a,20a-Dihydroxypregn-4-ene-3-one
  5. 17a,20a-Dihydroxyprogesterone
  6. 17a-Hydroxy-20a-dihydroprogesterone
  7. 20a-Dihydroxyprogesterone
  8. 3alpha,7alpha-Dihydroxy-5beta-cholestanate
  9. Pregn-4-ene-17a,20a-diol-3-one
Chemical Formula C21H32O3
Average Molecular Weight 332.477
Monoisotopic Molecular Weight 332.23514489
IUPAC Name (1S,2R,10R,11S,14S,15S)-14-hydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name (1S,2R,10R,11S,14S,15S)-14-hydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number 652-69-7
SMILES [H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C21H32O3/c1-19-8-5-15(23)13-14(19)3-4-16-17(19)6-9-20(2)18(16)7-10-21(20,24)11-12-22/h13,16-18,22,24H,3-12H2,1-2H3/t16-,17+,18+,19+,20+,21+/m1/s1
InChI Key ABBVGECYEGYVPY-CEGNMAFCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 17 Hydroxy Steroid
  • 3 Keto Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
  • Tertiary Alcohol
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 5.321 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.036 g/L ALOGPS
LogP 2.79 ALOGPS
LogP 2.66 ChemAxon
LogS -3.96 ALOGPS
pKa (strongest acidic) 14.28 ChemAxon
pKa (strongest basic) -2.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 95.48 ChemAxon
Polarizability 39.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023238
KNApSAcK ID Not Available
Chemspider ID 96976 Link_out
KEGG Compound ID Not Available
BioCyc ID ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC Link_out
BiGG ID 44035 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB03851 Link_out
Metagene Link HMDB03851 Link_out
METLIN ID Not Available
PubChem Compound 107835 Link_out
PDB ID Not Available
ChEBI ID 16577 Link_out
References
Synthesis Reference Al-Awadi, Sameera; Afzal, Mohammed; Oommen, Sosamma. Studies on Geobacillus stearothermophilus-part V1: transformation of 17a-hydroxyprogesterone and 21-hydroxyprogesterone. Biocatalysis and Biotransformation (2007), 25(1), 43-50.
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available