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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 06:55:46 UTC
HMDB IDHMDB0000483
Secondary Accession Numbers
  • HMDB00483
Metabolite Identification
Common Name5b-Cholestane-3a,7a,12a,23S,25-pentol
Description5b-Cholestane-3a,7a,12a,23S,25-pentol belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. 5b-Cholestane-3a,7a,12a,23S,25-pentol is considered to be a practically insoluble (in water) and relatively neutral molecule. 5b-Cholestane-3a,7a,12a,23S,25-pentol has been found in human hepatic tissue tissue, and has also been detected in multiple biofluids, such as feces and urine. Within the cell, 5b-cholestane-3a,7a,12a,23S,25-pentol is primarily located in the membrane (predicted from logP) and cytoplasm.
Structure
Thumb
Synonyms
ValueSource
(23S)-5b-Cholestane-3a,7a,12a,23,25-pentolHMDB
(3alpha,5beta,7alpha,12alpha,23S)-Cholestane-3,7,12,23,25-pentolHMDB
Chemical FormulaC27H48O5
Average Molecular Weight452.667
Monoisotopic Molecular Weight452.350174646
IUPAC Name(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
CAS Registry Number59906-15-9
SMILES
[H]C1CC([C@@H](C)C[C@H](O)CC(C)(C)O)[C@]2(C)C1[C@]1([H])[C@H](O)C[C@]3([H])C[C@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H]2O
InChI Identifier
InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20?,21-,22+,23-,24-,26-,27+/m0/s1
InChI KeyOXSBBBPDYVCAKC-CTSLUMRNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentPentahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Pentahydroxy bile acid, alcohol, or derivatives
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • 23-hydroxysteroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.052 g/LALOGPS
logP2.33ALOGPS
logP2.05ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)14.93ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.34 m³·mol⁻¹ChemAxon
Polarizability53.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3324900000-ce081905e393e80511e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1221019000-7bbdaca94cf9b3989863View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-ef4a2790d00f39151d5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2005900000-a3c8abf978fcc74e3e28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-4209700000-0530fc30e51b3d5bdd05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0002900000-33ffd4c8b139bf760226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3004900000-c80999c8f40ac84967fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9002000000-142d4259a51c5ae1ddecView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022068
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5470
PubChem Compound53477695
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHoshita, Takahiko; Yasuhara, Misao; Kihira, Kenji; Kuramoto, Taiju. Comparative biochemical studies of bile acids and bile alcohols. V. Identification of (23S)-5a-cholestane-3a,7a,12a,23,25-pentol in cerebrotendinous xanthomatosis. Steroids (1976), 27(5), 657-64.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kihira K, Kubota A, Hoshita T: Absolute configuration at carbon 23 of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol excreted by patients with cerebrotendinous xanthomatosis. J Lipid Res. 1984 Aug;25(8):871-5. [PubMed:6491531 ]
  2. Une M, Harada J, Mikami T, Hoshita T: High-performance liquid chromatographic separation of ultraviolet-absorbing bile alcohol derivatives. J Chromatogr B Biomed Appl. 1996 Jun 28;682(1):157-61. [PubMed:8832436 ]
  3. Shimazu K, Kuwabara M, Yoshii M, Kihira K, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. J Biochem. 1986 Feb;99(2):477-83. [PubMed:3700361 ]
  4. Kosaka D, Hiraoka T, Kohoda T, Kajiyama G, Yamauchi T, Kihira K, Kuramoto T, Hoshita T: Stable isotope dilution assay for 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,23,25-pentol in human serum using [26,27-D6] labeled internal standards; a highly accurate approach to the serological diagnosis of cerebrotendinous xanthomatosis. Clin Chim Acta. 1991 May 31;199(1):83-9. [PubMed:1934504 ]