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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-02-26 21:23:50 UTC
HMDB IDHMDB0002126
Secondary Accession Numbers
  • HMDB02126
Metabolite Identification
Common Name27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol
Description27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol, also known as 27-nor-pentol or 27-NC-3,7,12,24,25-po, 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. Thus, 27-nor-5b-cholestane-3a,7a,12a,24,25-pentol is considered to be a sterol lipid molecule. 27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752230
Synonyms
ValueSource
27-Nor-pentolHMDB
26(Or 27)-norcholestane-3,7,12,24,25-pentolHMDB
27-NC-3,7,12,24,25-POHMDB
27-Nor-5beta-cholestane-3alpha,7alpha,12alpha,24xi,25xi-pentolHMDB
27-Nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentolHMDB
27-Norcholestane-3,7,12,24,25-pentolHMDB
Chemical FormulaC26H46O5
Average Molecular Weight438.6404
Monoisotopic Molecular Weight438.334524582
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxyheptan-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)-5,6-dihydroxyheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
CAS Registry Number78648-95-0
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)CCC(O)C(C)O
InChI Identifier
InChI=1S/C26H46O5/c1-14(5-8-21(29)15(2)27)18-6-7-19-24-20(13-23(31)26(18,19)4)25(3)10-9-17(28)11-16(25)12-22(24)30/h14-24,27-31H,5-13H2,1-4H3/t14-,15?,16+,17-,18-,19+,20+,21?,22-,23+,24+,25+,26-/m1/s1
InChI KeyUBCPEZWGUOSYHO-JAPSQKQGSA-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-skeleton
  • Pentahydroxy bile acid, alcohol, or derivatives
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • 24-hydroxysteroid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.087 g/LALOGPS
logP2.18ALOGPS
logP2.15ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.43 m³·mol⁻¹ChemAxon
Polarizability51.95 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, Positivesplash10-006x-3229600000-bde346ae970774e09ec0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000l-2312139000-ec065a51350c2f3ac2ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-cc0f5824c365fd20cfceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0007900000-7f95ca196345a03eec2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7k-2109200000-fdbadaad91d1532f31afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0000900000-5b51895657efd481db50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0170-0006900000-925b9196b9209512a69aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9003200000-64f6e15616da4d1f8a42Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022855
KNApSAcK IDNot Available
Chemspider ID13628319
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6498
PubChem Compound21252278
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceUne M; Takenaka S; Kuramoto T; Fujimura K; Hoshita T; Kihira K Structural and biosynthetic studies of a principal bile alcohol, 27-nor-5beta-cholestane-3alpha,7alpha,12alpha,24,25-pentol, in human urine. Journal of lipid research (2000), 41(10), 1562-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available