Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.
Record Information
Version1.0
Creation Date2016-09-30 22:42:49 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0001231
Secondary Accession Numbers
  • BMDB01231
Metabolite Identification
Common Name27-Deoxy-5b-cyprinol
Description27-Deoxy-5b-cyprinol, also known as 5-CTTL, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Thus, 27-deoxy-5b-cyprinol is considered to be a bile acid lipid molecule. 27-Deoxy-5b-cyprinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrolChEBI
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestaneChEBI
5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrolChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraolChEBI
Cholestane-3,7,12,26(27)-tetrolChEBI
Cholestane-3,7,12,26-tetrolChEBI
Cholestane-3,7,12,27-tetrolChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrolKegg
(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrolGenerator
(3Α,5β,7α,12α)-cholestane-3,7,12,26-tetrolGenerator
3a,7a,12a,26-Tetrahydroxy-5b-cholestaneGenerator
3Α,7α,12α,26-tetrahydroxy-5β-cholestaneGenerator
5b-Cholestane 3a,7a,12a,27-tetrolGenerator
5Β-cholestane 3α,7α,12α,27-tetrolGenerator
5b-Cholestane-3a,7a,12a,26-tetraolGenerator
5Β-cholestane-3α,7α,12α,26-tetraolGenerator
5b-Cholestane-3a,7a,12a,26-tetrolGenerator
5Β-cholestane-3α,7α,12α,26-tetrolGenerator
(25R)-5-beta-Cholestane-3-alpha,7-alpha,12-alpha,26-tetraolHMDB
5-b-Cholestane-3a-7-tetraolHMDB
5-beta-Cholestane-3-alpha-7-alpha-12-alpha-26-tetraolHMDB
5-beta-Cholestane-3a-7-tetraolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetraolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetrolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27alpha-tetrolHMDB
5 beta-Cholestane-3alpha,7alpha,12alpha,26-tetrolHMDB
5-CTTLHMDB
Cholestane-3,7,12,26-tetrol, (3alpha,5alpha,7alpha,12alpha)-isomerHMDB
Chemical FormulaC27H48O4
Average Molecular Weight436.6676
Monoisotopic Molecular Weight436.355260024
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number862-53-3
SMILESNot Available
InChI Identifier
InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyXJZGNVBLVFOSKJ-XZULNKEGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001231
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022502
KNApSAcK IDNot Available
Chemspider ID167758
KEGG Compound IDC05446
BioCyc IDNot Available
BiGG ID45828
Wikipedia LinkNot Available
METLIN ID6095
PubChem Compound193321
PDB IDNot Available
ChEBI ID17278
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
Reactions
5-b-Cholestane-3a ,7a ,12a-triol + 3 NADPH + 3 Oxygen → 27-Deoxy-5b-cyprinol +3 NADP +4 Waterdetails
27-Deoxy-5b-cyprinol + 3 NADPH + 3 Oxygen → 3a,7a,12a-Trihydroxy-5b-cholestan-26-al +3 NADP +4 Waterdetails