Record Information
Version1.0
Creation date2011-09-21 00:15:00 UTC
Update date2015-07-21 06:57:14 UTC
Primary IDFDB022502
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name27-Deoxy-5beta-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) [HMDB]
CAS Number862-53-3
Structure
Thumb
Synonyms
SynonymSource
(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
(25R)-5-beta-cholestane-3-alpha,7-alpha,12-alpha,26-tetraolhmdb
(3α,5β,7α,12α)-cholestane-3,7,12,26-tetrolGenerator
27-Deoxy-5b-cyprinolhmdb
3α,7α,12α,26-tetrahydroxy-5β-cholestaneGenerator
5-beta-cholestane-3-alpha-7-alpha-12-alpha-26-tetraolhmdb
5beta-cholestane-3alpha,7alpha,12alpha,27-tetraolhmdb
5beta-cholestane-3alpha,7alpha,12alpha,27-tetrolhmdb
5beta-cholestane-3alpha,7alpha,12alpha,27alpha-tetrolhmdb
5β-cholestane 3α,7α,12α,27-tetrolGenerator
5β-cholestane-3α,7α,12α,26-tetraolGenerator
5β-cholestane-3α,7α,12α,26-tetrolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.73 m³·mol⁻¹ChemAxon
Polarizability53.38 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H48O4
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight436.6676
Monoisotopic Molecular Weight436.355260024
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05vx-0539800000-97d0e900e0ff8088e8aeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2210079000-59774cc66a8ee849736fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-a7bb325d6ee8da922144View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1004900000-c638ee962db83c052bc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2109100000-69c195557b16f6759fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0001900000-ac185007bede2c767651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0003900000-c665bc9fb94b91ab203eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2009400000-5648c1610aafe0315c85View in MoNA
ChemSpider ID167758
ChEMBL IDNot Available
KEGG Compound IDC05446
Pubchem Compound ID193321
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01231
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45828
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
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