Cycloartenol (CHEM030260)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:46:30 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030260
Identification
Common NameCycloartenol
ClassSmall Molecule
DescriptionConstituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol. Cycloartenol is found in many foods, some of which are blackcurrant, sourdough, lemon, and leek.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9,19-Cyclo-9beta-lanost-24-en-3beta-olHMDB
9,19-Cycloart-24-ene, 3beta-olHMDB
9beta,19-Cyclo-24-lanosten-3beta-olHMDB
9beta,19-Cyclolanost-24-en-3beta-olHMDB
ArtosenolHMDB
HandianolHMDB
CycloarterenolMeSH
CycloartenolMeSH
Chemical FormulaC30H50O
Average Molecular Mass426.717 g/mol
Monoisotopic Mass426.386 g/mol
CAS Registry Number469-38-5
IUPAC Name7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
Traditional Name7,7,12,16-tetramethyl-15-(6-methylhept-5-en-2-yl)pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
SMILESCC(CCC=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C
InChI IdentifierInChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3
InChI KeyONQRKEUAIJMULO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCycloartanols and derivatives
Direct ParentCycloartanols and derivatives
Alternative Parents
Substituents
  • Cycloartanol-skeleton
  • Triterpenoid
  • Cycloartane-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6e-05 g/LALOGPS
logP6.66ALOGPS
logP7.55ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity132.03 m³·mol⁻¹ChemAxon
Polarizability55.07 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-3129500000-84dc7a934204a370748aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00lr-4011900000-88cf4a746167f7db19cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0003900000-ab3e1619815ddc34b3aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1019400000-e52ce1479e1220bb23e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-2039000000-28a8e4b53c1973a3ebd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-459890f27580d9795c97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-280c456ab6df8a80788dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-74ba59f4db9c4a4d312cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036591
FooDB IDFDB015503
Phenol Explorer IDNot Available
KNApSAcK IDC00003650
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCycloartenol
Chemspider ID437607
ChEBI ID17030
PubChem Compound ID500213
Kegg Compound IDC01902
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ahumada C, Saenz T, Garcia D, De La Puerta R, Fernandez A, Martinez E: The effects of a triterpene fraction isolated from Crataegus monogyna Jacq. on different acute inflammation models in rats and mice. Leucocyte migration and phospholipase A2 inhibition. J Pharm Pharmacol. 1997 Mar;49(3):329-31.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM