Showing metabocard for 27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol (BMDB0002126)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:29 UTC
Update Date2020-04-22 15:09:50 UTC
BMDB IDBMDB0002126
Secondary Accession Numbers
  • BMDB02126
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-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. Based on a literature review a significant number of articles have been published on 27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
27-Nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentolMeSH
26(Or 27)-norcholestane-3,7,12,24,25-pentolMeSH
27-Nor-5beta-cholestane-3alpha,7alpha,12alpha,24xi,25xi-pentolMeSH
27-Norcholestane-3,7,12,24,25-pentolMeSH
27-NC-3,7,12,24,25-POMeSH
27-Nor-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-3229600000-bde346ae970774e09ec0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000l-2312139000-ec065a51350c2f3ac2ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-cc0f5824c365fd20cfceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0007900000-7f95ca196345a03eec2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7k-2109200000-fdbadaad91d1532f31afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0000900000-5b51895657efd481db50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0170-0006900000-925b9196b9209512a69aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9003200000-64f6e15616da4d1f8a42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-05a37b1f6fb26630dbdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-0009500000-8c13ec7e85cc9fc19b0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1003900000-b4a62bd7583e7d46d470View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-332cdd56e858cd4a6c1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2223900000-d40bd776a59811df356eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-9641000000-5493df5ef7af75d8c768View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002126
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
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