You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:16 UTC
HMDB IDHMDB0000513
Secondary Accession Numbers
  • HMDB0000519
  • HMDB0000587
  • HMDB00513
  • HMDB00519
  • HMDB00587
Metabolite Identification
Common Name5b-Cholestane-3a,7a,12a,23R,25-pentol
Description5b-Cholestane-3a,7a,12a,23R,25-pentol is a bile alcohol present in the urine of patients with cerebrotendinous xanthomatosis, but not in feces. A possible explanation for the urinary cholestanepentols is that the major serum bile alcohol, 5b-cholestane-3a,7a,12a,25-tetrol, might be hydroxylated at C-23 to form (23)-5b-cholestane-3a,7a,12a,23,25-pentols in the kidneys, an hypothesis supported by the fact that in our patient (23R)-5b-cholestane-3a,7a,12a,23,25-pentol was detected only in urine but were virtually absent in bile. (PMID 3700361 ).
Structure
Data?1582752136
Synonyms
ValueSource
1-Nonanecarboxylic acidChEBI
10:0ChEBI
C10:0ChEBI
Caprinic acidChEBI
CH3-[CH2]8-COOHChEBI
DecanoateChEBI
Decoic acidChEBI
Decylic acidChEBI
DekansaeureChEBI
KaprinsaeureChEBI
N-Capric acidChEBI
N-Decanoic acidChEBI
N-Decoic acidChEBI
N-Decylic acidChEBI
1-NonanecarboxylateGenerator
CaprinateGenerator
Decanoic acidGenerator
DecoateGenerator
DecylateGenerator
N-CaprateGenerator
N-DecanoateGenerator
N-DecoateGenerator
N-DecylateGenerator
CaprateGenerator
CaprynateHMDB
Caprynic acidHMDB
Emery 659HMDB
Lunac 10-95HMDB
Lunac 10-98HMDB
Prifac 2906HMDB
Prifac 296HMDB
Decanoic acid, sodium saltHMDB
Sodium caprateHMDB
Sodium decanoateHMDB
FA(10:0)HMDB
17-(3,5-Dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triolHMDB
Chemical FormulaC27H48O5
Average Molecular Weight452.667
Monoisotopic Molecular Weight452.350174646
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-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,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
CAS Registry Number59906-14-8
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)C[C@@H](O)CC(C)(C)O
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-/m1/s1
InChI KeyOXSBBBPDYVCAKC-DYGXNTOZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
Polarizability53.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3324900000-4eb492177cd3ff3b1d78Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ue9-1620339000-8ab1e57d5c6fb0da7063Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-ef4a2790d00f39151d5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2005900000-a3c8abf978fcc74e3e28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-4209700000-0530fc30e51b3d5bdd05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0002900000-33ffd4c8b139bf760226Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3004900000-c80999c8f40ac84967fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9002000000-142d4259a51c5ae1ddecSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03600
Phenol Explorer Compound IDNot Available
FooDB IDFDB012027
KNApSAcK IDC00001213
Chemspider ID2863
KEGG Compound IDC01571
BioCyc IDCPD-3617
BiGG IDNot Available
Wikipedia LinkDecanoic acid
METLIN ID336
PubChem Compound2969
PDB IDNot Available
ChEBI ID30813
Food Biomarker OntologyNot Available
VMH IDDCA
MarkerDB ID
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. Kimura M, Yamaguchi S: Screening for fatty acid beta oxidation disorders. Acylglycine analysis by electron impact ionization gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):105-10. [PubMed:10491995 ]
  2. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  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. (). Mayo Medical Laboratories 2005 Test Catalog. .