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Human Metabolome Database Version 3.5

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Showing metabocard for 7 alpha,26-Dihydroxy-4-cholesten-3-one (HMDB12459)

Record Information
Version 3.5
Creation Date 2009-07-13 08:03:09 -0600
Update Date 2013-02-08 17:29:11 -0700
HMDB ID HMDB12459
Secondary Accession Numbers None
Metabolite Identification
Common Name 7 alpha,26-Dihydroxy-4-cholesten-3-one
Description 7 alpha,26-Dihydroxy-4-cholesten-3-one is involved in primary bile acid biosynthesis. 7 alpha,26-Dihydroxy-4-cholesten-3-one is produced from 7 alpha,27-Dihydroxycholesterol through the action of HSD3B7 (EC:1.1.1.181). 7 alpha,26-Dihydroxy-4-cholesten-3-one can then be converted to 7 alpha-Hydroxy-3-oxo-4-cholestenoate by CYP27A (EC:1.14.13.15).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (7alpha)-7,26-dihydroxy-Cholest-4-en-3-one
  2. 4-Cholesten-7alpha,26-diol-3-one
  3. 7,26-Dhxyclso
  4. 7alpha,26-Dihydroxy-4-cholesten-3-one
  5. 7alpha,26-dihydroxycholest-4-en-3-one
Chemical Formula C27H44O3
Average Molecular Weight 416.6365
Monoisotopic Molecular Weight 416.329045274
IUPAC Name (2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name (2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number 4675-38-1
SMILES CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17?,18-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI Key KVJVJJWIEXCECB-JZGXDVPNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Bile Acids, Alcohols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Bile Acids, Alcohols and Derivatives
  • Sesterterpenes
Substituents
  • 27 Hydroxy Steroid
  • 3 Keto Steroid
  • 7 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Fatty Alcohol
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Dihydroxy Bile Acids, Alcohols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0029 g/L ALOGPS
LogP 4.60 ALOGPS
LogP 5.01 ChemAxon
LogS -5.16 ALOGPS
pKa (strongest acidic) 17.14 ChemAxon
pKa (strongest basic) -0.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 123.01 ChemAxon
Polarizability 50.79 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 map00120 Link_out
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 FDB029075
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C17336 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12459 Link_out
Metagene Link HMDB12459 Link_out
METLIN ID Not Available
PubChem Compound 53481412 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Sterol 26-hydroxylase, mitochondrial
Reactions:
    Gene Name: CYP27A1
    Uniprot ID: Q02318 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 3 beta-hydroxysteroid dehydrogenase type 7
    Reactions:
      Gene Name: HSD3B7
      Uniprot ID: Q9H2F3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA