Record Information
Version1.0
Creation date2011-09-21 01:45:37 UTC
Update date2015-07-21 06:59:32 UTC
Primary IDFDB028826
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4alpha-Hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol
Description4Alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from 4-alpha-methylzymosterol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
4a-Hydroxymethyl-5a-cholesta-8,24-dien-3b-olGenerator
4Α-hydroxymethyl-5α-cholesta-8,24-dien-3β-olGenerator
4 alpha-Hysroxymethyl-5 alpha-cholsta-8,24-dien-3 beta-olHMDB
4-alpha-Hysroxymethyl-5-alpha-cholsta-8,24-dien-3-beta-olHMDB
4 alpha-hysroxymethyl-5 alpha-cholsta-8,24-dien-3 beta-olhmdb
4-alpha-hysroxymethyl-5-alpha-cholsta-8,24-dien-3-beta-olhmdb
4a-hydroxymethyl-5a-cholesta-8,24-dien-3b-olhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP5.55ALOGPS
logP5.63ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.5 m³·mol⁻¹ChemAxon
Polarizability52.07 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H46O2
IUPAC name(2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
InChI IdentifierInChI=1S/C28H46O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,19,21-24,26,29-30H,6,8-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1
InChI KeyORZKEIGPXNMCHC-GYISYUOESA-N
Isomeric SMILESCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC3
Average Molecular Weight414.6636
Monoisotopic Molecular Weight414.349780716
Classification
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-1009000000-26a6475677afe7b86ff0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-3101390000-9a7be192c5b850bae998View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009200000-6a505952adf6b44c3471View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-2019000000-bfa43bfa929440dc0886View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07br-3229000000-f36e1263e8ba538a453eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0005900000-10de80058b799a204f93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yj-0009300000-6ac3a41026db556615bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0009000000-3023571b31cb46c00627View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25202625
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12172
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference