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Showing Compound (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol (FDB028340)

Record Information
Version1.0
Creation date2011-09-21 01:38:14 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028340
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol
Description(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is a hydroxysterol and a bile acid intermediate. It is produced from the reaction of 24(R)-Hydroxycholesterol with the enzyme CYP39A, which is also known as 24-hydroxycholesterol 7alpha-hydroxylase (EC 1.14.13.99). This enzyme catalyzes the following reaction: (24R)-cholest-5-ene-3beta,24-diol + NADPH + H+ O2 = (24R)-cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O. This leads to the 7-alpha hydroxylation of 24(R)-hydroxycholesterol. This enzyme can act on both the 24R and 24S isomers. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(24R)-Cholest-5-ene-3-b,7-a,24-triolGenerator
(24R)-Cholest-5-ene-3-β,7-α,24-triolGenerator
(24R)-Cholest-5-ene 3-b,7-a,24-triolHMDB
(24R)-Cholest-5-ene-3beta,7alpha,24-triolHMDB
5a-Cholesta-7,24-dien-3-b-olHMDB
5a-Cholesta-7,24-dien-3-beta-olHMDB
(24R)-cholest-5-ene 3-b,7-a,24-triolhmdb
(24R)-cholest-5-ene-3beta,7alpha,24-triolhmdb
5a-cholesta-7,24-dien-3-b-olhmdb
5a-cholesta-7,24-dien-3-beta-olhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0085 g/LALOGPS
logP4.28ALOGPS
logP4.65ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.65 m³·mol⁻¹ChemAxon
Polarizability51.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H46O3
IUPAC name(1S,2R,5S,9S,10S,11S,15R)-14-[(2R,5R)-5-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/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h15-17,19-25,28-30H,6-14H2,1-5H3/t17-,19+,20?,21+,22+,23-,24-,25+,26+,27-/m1/s1
InChI KeyZNCHPOYZMVVJCK-DPFMVWRKSA-N
Isomeric SMILES[H][C@@]12CCC([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
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
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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

Industrial application:

Biological role:

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-MS(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1239400000-cd1b8c75eaf66591d8c2Spectrum
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-2110149000-138cf2097993192ea364Spectrum
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(24R)-Cholest-5-ene-3-beta,7-alpha,24-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0007900000-17814845dbf0bec54cfd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-3009400000-fd95622ed3f4f1fae1c42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-5029000000-70e1fb26560a91668d822017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0005900000-a892257c0a1e6d75d1d92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009500000-66d60259ffcab13684b42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fl9-7009200000-99af00a0dfd9097d149b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-f2cb6399034352e924c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1002900000-b6143eba8eae9ed9668b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-3019800000-4bfcf5c6acaa256d75992021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-0308900000-66129b219db1313f72732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3329100000-91ec216cab7fcf837baf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-3943000000-12a20d116574d822ddef2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481010
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11644
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
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