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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:03 UTC
HMDB IDHMDB01231
Secondary Accession Numbers
  • HMDB06264
Metabolite Identification
Common Name27-Deoxy-5b-cyprinol
Description27-Deoxy-5b-cyprinol is an intermediate in Bile acid synthesis pathway, in a sequence of reactions catalyzed by sterol 27-hydroxylase (CYP27) in the oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid (PMID: 8496170 ). 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol 3-glucuronide, a metabolite of 27-Deoxy-5b-cyprinol, is the major bile alcohol component in serum from cerebrotendinous xanthomatosis patients (PMID: 7920441 ).
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
(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrolGenerator
(3α,5β,7α,12α)-cholestane-3,7,12,26-tetrolGenerator
5b-Cholestane-3a,7a,12a,26-tetrolGenerator
5β-cholestane-3α,7α,12α,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
(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
Chemical FormulaC27H48O4
Average Molecular Weight436.6676
Monoisotopic Molecular Weight436.355260024
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name5-cttl
CAS Registry Number862-53-3
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO
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 KeyInChIKey=XJZGNVBLVFOSKJ-XZULNKEGSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 26-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 mg/mLALOGPS
logP3.77ALOGPS
logP3.62ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.73 m3·mol-1ChemAxon
Polarizability53.38 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022502
KNApSAcK IDNot Available
Chemspider ID167758
KEGG Compound IDC05446
BioCyc ID5-BETA-CHOLESTANE-3-ALPHA7-TETRAOL
BiGG ID45828
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01231
Metagene LinkHMDB01231
METLIN ID6095
PubChem Compound193321
PDB IDNot Available
ChEBI ID17278
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. J Biol Chem. 1993 May 25;268(15):11079-85. [8496170 ]
  2. Ohshima A, Kuramoto T, Hoshita T: Biochemical studies of inherited diseases related to abnormal cholesterol metabolism. I. High-performance liquid chromatographic analysis of bile alcohol glucuronides in cerebrotendinous xanthomatosis. Biol Pharm Bull. 1994 May;17(5):721-3. [7920441 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
5-b-Cholestane-3a ,7a ,12a-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Waterdetails
27-Deoxy-5b-cyprinol → 3a,7a,12a-Trihydroxy-5b-cholestan-26-aldetails