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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:41:41 UTC
HMDB IDHMDB0001203
Secondary Accession Numbers
  • HMDB01203
Metabolite Identification
Common Name4a-Formyl-5a-cholesta-8,24-dien-3b-ol
Description4a-Formyl-5a-cholesta-8,24-dien-3b-ol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 4a-Formyl-5a-cholesta-8,24-dien-3b-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752184
Synonyms
ValueSource
4alpha-Formyl-5alpha-cholesta-8,24-dien-3beta -olHMDB
Chemical FormulaC28H44O2
Average Molecular Weight412.6478
Monoisotopic Molecular Weight412.334130652
IUPAC Name5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde
Traditional Name5-hydroxy-2,15-dimethyl-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(CCC12C)C1(C)CCC(O)C(C=O)C1CC3
InChI Identifier
InChI=1S/C28H44O2/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/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3
InChI KeyZLQSSFNCEUGGJF-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0018 g/LALOGPS
logP10(6.11) g/LALOGPS
logP10(5.88) g/LChemAxon
logS10(-5.4) g/LALOGPS
pKa (Strongest Acidic)14.1ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.36 m³·mol⁻¹ChemAxon
Polarizability51.47 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]+195.95131661259
DarkChem[M-H]-192.96131661259
AllCCS[M+H]+208.30632859911
AllCCS[M-H]-208.24732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4a-Formyl-5a-cholesta-8,24-dien-3b-olCC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC32976.6Standard polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-olCC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC33377.5Standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-olCC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC33448.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,1TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C)C(C=O)C1CC33503.6Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,1TMS,isomer #2CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O)C(=CO[Si](C)(C)C)C1CC33425.5Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC33444.5Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC33382.6Standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C)C(=CO[Si](C)(C)C)C1CC33640.7Standard polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,1TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)C(C=O)C1CC33722.1Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,1TBDMS,isomer #2CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O)C(=CO[Si](C)(C)C(C)(C)C)C1CC33656.9Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC33894.5Semi standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC33887.8Standard non polar33892256
4a-Formyl-5a-cholesta-8,24-dien-3b-ol,2TBDMS,isomer #1CC(C)=CCCC(C)C1CCC2C3=C(CCC21C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)C1CC33846.6Standard 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 IDFDB022489
KNApSAcK IDNot Available
Chemspider ID570845
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6079
PubChem Compound656456
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 ReferencesNot Available