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Showing Compound Cholestane-3,7,12,24,25-pentol (FDB022908)

Record Information
Version1.0
Creation date2011-09-21 00:21:33 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022908
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCholestane-3,7,12,24,25-pentol
DescriptionCholestane-3,7,12,24,25-pentol is the major bile alcohol identified in urine from healthy humans, both in children and adults. Bile alcohols have been found to be present as minor components in the bile and urine in healthy subjects. Bile alcohols are end products for cholesterol elimination as well as major biliary constituents; in mammals, cholesterol is metabolized by additional enzymes that ultimately transform it to bile acids. Bile alcohols are preferentially excreted as glucuronides into the urine, which constitute about 10% of total bile acids. The excretion of glucuronidated bile alcohols in urine is suggested to reflect an alternative metabolism of intermediates in the normal biosynthesis of bile acids. Patients with the rare inherited sterol storage disease, cerebrotendinous xanthomatosis, accumulation bile alcohols in bile and feces.(PMID: 6726087, 6548247, 11718684) [HMDB]
CAS Number58580-61-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.54ALOGPS
logP2.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.85ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.07 m³·mol⁻¹ChemAxon
Polarizability53.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H48O5
IUPAC name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
InChI IdentifierInChI=1S/C27H48O5/c1-15(6-9-22(30)25(2,3)32)18-7-8-19-24-20(14-23(31)27(18,19)5)26(4)11-10-17(28)12-16(26)13-21(24)29/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17-,18-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1
InChI KeyNHPWQASMMFUHIZ-YBMOUMCLSA-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)CC[C@H](O)C(C)(C)O
Average Molecular Weight452.667
Monoisotopic Molecular Weight452.350174646
Classification
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
  • Pentahydroxy bile acid, alcohol, or derivatives
  • 25-hydroxysteroid
  • 24-hydroxysteroid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCholestane-3,7,12,24,25-pentol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-5225900000-7bfe77e73e7fc24ad195Spectrum
Predicted GC-MSCholestane-3,7,12,24,25-pentol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-1322129000-1ee58111be3f38bfe31aSpectrum
Predicted GC-MSCholestane-3,7,12,24,25-pentol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0001900000-cdb2ed65e69d8df890ff2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1004900000-4f5b915308d8cc197d262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-3109700000-c919e36c46d0c17d51ee2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0000900000-32cdd9e3f773b9c66cdf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0004900000-8e0b2f488aa99497b2652017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ri-9002500000-971f342cc22704f557d92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0001900000-824b9d3ad57ad4f164862021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ftv-4477900000-e8837317e3485190852f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004m-6951000000-00ad768b7d9da74502f82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6df22a99e7d0a9fae0b12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-0006900000-63a49e7ab4159da2ebfc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0003900000-ee43a4f1e19159b4dd912021-09-24View Spectrum
NMRNot Available
ChemSpider ID4956022
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6453659
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02208
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference