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Showing Compound 7alpha,27-Dihydroxycholesterol (FDB023875)

Record Information
Version1.0
Creation date2011-09-21 00:36:10 UTC
Update date2015-07-21 06:57:55 UTC
Primary IDFDB023875
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7alpha,27-Dihydroxycholesterol
Description7-a,27-Dihydroxycholesterol, also known as cholest-5-ene-3b,7a,26-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Thus, 7-a,27-dihydroxycholesterol is considered to be a bile acid lipid molecule. 7-a,27-Dihydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number4725-24-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
5-Cholestene-3beta,7alpha,26-triolChEBI
7-alpha,27-DihydroxycholesterolChEBI
Cholest-5-ene-3beta,7alpha,26-triolChEBI
Cholest-5-ene-3beta,7alpha,27-triolChEBI
5-Cholestene-3b,7a,26-triolGenerator
5-Cholestene-3β,7α,26-triolGenerator
7-Α,27-dihydroxycholesterolGenerator
Cholest-5-ene-3b,7a,26-triolGenerator
Cholest-5-ene-3β,7α,26-triolGenerator
Cholest-5-ene-3b,7a,27-triolGenerator
Cholest-5-ene-3β,7α,27-triolGenerator
7alpha,26-DihydroxycholesterolHMDB
7alpha,27-DihydroxycholesterolHMDB
Cholest-5-ene-3,7,27-triolHMDB
Cholest-5-ene-3- b,7-a,27-triolHMDB
Cholest-5-ene-3-b,7-a,27-triolHMDB
Cholest-5-ene-3-beta,7-alpha,27-triolHMDB
7-a,27-DihydroxycholesterolGenerator
7-α,27-dihydroxycholesterolGenerator
7alpha,26-dihydroxycholesterolhmdb
cholest-5-ene-3- b,7-a,27-triolhmdb
cholest-5-ene-3-beta,7-alpha,27-triolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0051 g/LALOGPS
logP4.67ALOGPS
logP4.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.91 m³·mol⁻¹ChemAxon
Polarizability52.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H46O3
IUPAC name(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
InChI IdentifierInChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyRXMHNAKZMGJANZ-DTTSCKGMSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
Classification
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS7alpha,27-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0139300000-221e3200779e0697d017Spectrum
Predicted GC-MS7alpha,27-Dihydroxycholesterol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-1310149000-0a3195294de24630bcb5Spectrum
Predicted GC-MS7alpha,27-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0006900000-c1354f70aeba87e8bddf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1009300000-a1e89f6c04fc2d2865d12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-062c-3029000000-d0d93103295de6ed3d2c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0006900000-6b334d55dd76faff4df82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009400000-c2983b5dbb3cbfbf357e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-2009100000-2e80feb58d681f70a6f92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-a0815d1227c30636020c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0003900000-810b115febb00f469d252021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0003900000-558c2f025f3c29e2e9522021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1202900000-bd6f4c8c658841ee2d202021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6359400000-afbc03ffc36e1b4230242021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-7950000000-0145ada702a586b3b6642021-09-25View Spectrum
NMRNot Available
ChemSpider ID389810
ChEMBL IDNot Available
KEGG Compound IDC06341
Pubchem Compound ID440985
Pubchem Substance IDNot Available
ChEBI ID18431
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06281
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID48023
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference