Record Information
Version1.0
Creation date2011-09-21 00:19:36 UTC
Update date2015-07-21 06:57:21 UTC
Primary IDFDB022786
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7a-Hydroxy-cholestene-3-one
Description7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217) [HMDB]
CAS Number3862-25-7
Structure
Thumb
Synonyms
SynonymSource
7alpha-Hydroxy-4-cholesten-3-oneChEBI
Cholest-4-en-7alpha-ol-3-oneChEBI
7a-Hydroxy-4-cholesten-3-oneGenerator
7Α-hydroxy-4-cholesten-3-oneGenerator
Cholest-4-en-7a-ol-3-oneGenerator
Cholest-4-en-7α-ol-3-oneGenerator
7 alpha-3Ox-CHMDB
7 alpha-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxycholest-4-en-3-oneHMDB
7-alpha-Hydroxy-4-cholesten-3-oneHMDB
7-alpha-Hydroxycholest-4-en-3-oneHMDB
7-Hydroxycholest-4-en-3-oneHMDB
7a-Hydroxy-4-cholesten-3-one-12alphaHMDB
7alpha-Hydroxycholest-4-en-3-oneHMDB
HCOHMDB
Cholest-4-en-7 alpha-ol-3-oneHMDB
7-Hydroxy-4-cholesten-3-oneHMDB
7 alpha-3ox-Chmdb
7 alpha-hydroxy-4-cholesten-3-onehmdb
7-a-hydroxy-4-cholesten-3-onehmdb
7-a-hydroxycholest-4-en-3-onehmdb
7-alpha-hydroxy-4-cholesten-3-onehmdb
7-alpha-hydroxycholest-4-en-3-onehmdb
7a-Hydroxycholest-4-en-3-oneGenerator
7α-hydroxy-4-cholesten-3-oneGenerator
7α-hydroxycholest-4-en-3-oneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.00017 g/LALOGPS
logP5.46ALOGPS
logP6.37ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.16 m³·mol⁻¹ChemAxon
Polarizability50.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H44O2
IUPAC name(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyIOIZWEJGGCZDOL-RQDYSCIWSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
Classification
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1339000000-8b87f8914863b4c7e8e7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a6r-4672900000-f5cd21522bdf7607c5cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019500000-764a74c3942ad452aa8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-3339100000-87e6e598932d57a6274eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-8469000000-b55e4f0de6f6dbfbe093JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b03a7cbfe5ca7374d51fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-903f15d46f6bf7449623JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1009000000-fd9c44e4f27a3c62b7e8JSpectraViewer
ChemSpider ID110306
ChEMBL IDNot Available
KEGG Compound IDC05455
Pubchem Compound ID123743
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01993
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45848
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHCO
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference