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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:20 UTC
Update Date2021-09-14 15:41:41 UTC
HMDB IDHMDB0012167
Secondary Accession Numbers
  • HMDB12167
Metabolite Identification
Common Name4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol
Description4alpha-formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis I and in cholesterol biosynthesis III (via desmosterol). It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4alpha-carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol or from the enzymatic oxidation of 4alpha-hydroxymethyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis II 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. The sequence of reactions and the types of intermediates in cholesterol biosynthesis III (via desmosterol) 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. In cholesterol biosynthesis I, 4alpha-formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol is an intermediate in the conversion of lanosterol to cholesterol. The enzymology of this multistep conversion was largely determined in rat liver and the human pathway is therefore inferred from this work. Indeed, the order of some of the reactions in this pathway may vary. The lanosterol-to-cholesterol conversion involves the oxidative removal of three methyl groups, reduction of double bonds, and migration of the lanosterol double bond to a new position in cholesterol. The reactions in the lanosterol pathway are catalyzed by membrane-bound enzymes. Human genes have been identified for all the enzymes in this pathway and human disorders of cholesterol metabolism have been associated with genetic defects in most of these enzymes.
Structure
Data?1582753022
Synonyms
ValueSource
4a-Formyl-4b-methyl-5a-cholesta-8,24-dien-3b-olGenerator
4Α-formyl-4β-methyl-5α-cholesta-8,24-dien-3β-olGenerator
4a-Formyl-4beta-methyl-5a-cholesta-8,24-dien-3beta-olHMDB
4alpha-Formyl-4b-methyl-5alpha-cholesta-8,24-dien-3b-olHMDB
Chemical FormulaC29H46O2
Average Molecular Weight426.6743
Monoisotopic Molecular Weight426.349780716
IUPAC Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde
Traditional Name(2S,5S,6S,15R)-5-hydroxy-2,6,15-trimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC3
InChI Identifier
InChI=1S/C29H46O2/c1-19(2)8-7-9-20(3)22-11-12-23-21-10-13-25-28(5,24(21)14-16-27(22,23)4)17-15-26(31)29(25,6)18-30/h8,18,20,22-23,25-26,31H,7,9-17H2,1-6H3/t20?,22?,23?,25?,26-,27+,28+,29-/m0/s1
InChI KeyGFGANDKVOKQAGH-AEWFMJFUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP10(6.17) g/LALOGPS
logP10(6.44) g/LChemAxon
logS10(-5.6) g/LALOGPS
pKa (Strongest Acidic)14.54ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.86 m³·mol⁻¹ChemAxon
Polarizability53.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.7531661259
DarkChem[M-H]-192.93431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC33085.0Standard polar33892256
4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC33412.2Standard non polar33892256
4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-olCC(CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@](C)(C=O)C1CC33522.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol,1TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@](C)(C=O)C1CC33453.7Semi standard non polar33892256
4alpha-Formyl-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol,1TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@](C)(C=O)C1CC33667.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB028821
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25200700
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.