5b-Cholestane-3a,7a,12a,23R,25-pentol (CHEM034886)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:18:17 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034886
Identification
Common Name5b-Cholestane-3a,7a,12a,23R,25-pentol
ClassSmall Molecule
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).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
17-(3,5-Dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triolHMDB
Chemical FormulaC27H48O5
Average Molecular Mass452.667 g/mol
Monoisotopic Mass452.350 g/mol
CAS Registry Number59906-14-8
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
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 IdentifierInChI=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 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 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 Solubility0.052 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_8) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0409-0009700000-996ef26438e4bc39f389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-4279500000-ec27c905a89e055a39d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9850000000-991e1aa56ec25a12a3fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-31db0067a7126bac2473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-0003900000-68719f52b9a93bc9b349Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0003900000-c260caf34cf5aecd15cfSpectrum
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 IDHMDB0000513
FooDB IDFDB022085
Phenol Explorer IDNot Available
KNApSAcK IDC00001213
BiGG IDNot Available
BioCyc IDCPD-3617
METLIN ID336
PDB IDNot Available
Wikipedia LinkDecanoic acid
Chemspider ID13628096
ChEBI ID30813
PubChem Compound ID2969
Kegg Compound IDC01571
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hoshita, 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.
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.
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.
4. 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.
5. Mayo Medical Laboratories 2005 Test Catalog