27-Deoxy-5beta-cyprinol (CHEM035131)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:30:51 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035131
Identification
Common Name27-Deoxy-5beta-cyprinol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass436.668 g/mol
Monoisotopic Mass436.355 g/mol
CAS Registry Number862-53-3
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
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 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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05vx-0539800000-97d0e900e0ff8088e8aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2210079000-59774cc66a8ee849736fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-a7bb325d6ee8da922144Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1004900000-c638ee962db83c052bc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2109100000-69c195557b16f6759fe2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0001900000-ac185007bede2c767651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0003900000-c665bc9fb94b91ab203eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2009400000-5648c1610aafe0315c85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-70eabfb538b202d65e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-96d84b6ae4900e35a01eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0002900000-aedbb2b65b87f50fb926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fri-0000900000-260248684581f7f3ef51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-4322900000-e31a265ff7b793fc8577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9421000000-a3832dd065b12eca2a9aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001231
FooDB IDFDB022502
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45828
BioCyc IDNot Available
METLIN ID6095
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID167758
ChEBI ID17278
PubChem Compound ID193321
Kegg Compound IDC05446
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.