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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:59 UTC
Update Date2022-03-07 02:54:58 UTC
HMDB IDHMDB0036591
Secondary Accession Numbers
  • HMDB36591
Metabolite Identification
Common NameCycloartenol
DescriptionCycloartenol is found in alcoholic beverages. Cycloartenol is a constituent 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
Structure
Data?1595520745
Synonyms
ValueSource
9beta,19-Cyclo-24-lanosten-3beta-olChEBI
9b,19-Cyclo-24-lanosten-3b-olGenerator
9Β,19-cyclo-24-lanosten-3β-olGenerator
(3beta)-9,19-Cyclolanost-24-en-3-olHMDB
(3beta,9beta)-9,19-Cyclolanost-24-en-3-olHMDB
(3Β)-9,19-cyclolanost-24-en-3-olHMDB
(3Β,9β)-9,19-cyclolanost-24-en-3-olHMDB
9,19-Cyclo-24-lanosten-3beta-olHMDB
9,19-Cyclo-24-lanosten-3β-olHMDB
9,19-Cyclo-9beta-lanost-24-en-3beta-olHMDB
9,19-Cyclo-9β-lanost-24-en-3β-olHMDB
Cycloart-24(25)-enolHMDB
Cycloart-24-en-3beta-olHMDB
Cycloart-24-en-3β-olHMDB
HandianolHMDB
CycloarterenolMeSH
CycloartenolHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.729
Monoisotopic Molecular Weight426.38616623
IUPAC Name(3R,6S,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
Traditional Name(3R,6S,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
CAS Registry Number469-38-5
SMILES
[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=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/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
InChI KeyONQRKEUAIJMULO-YBXTVTTCSA-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
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point99 °CNot Available
Boiling Point505.46 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.3e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.305 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability54.82 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-244.55430932474
DeepCCS[M+Na]+218.36730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cycloartenol[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC=C(C)C2795.5Standard polar33892256
Cycloartenol[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC=C(C)C3313.1Standard non polar33892256
Cycloartenol[H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC=C(C)C3427.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloartenol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O[Si](C)(C)C)CC[C@@]45C[C@@]35CC[C@]12C3407.9Semi standard non polar33892256
Cycloartenol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]45C[C@@]35CC[C@]12C3615.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cycloartenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 10V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 20V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 40V, Negative-QTOFsplash10-004i-0001900000-490923fd56ae6a2d02522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 10V, Positive-QTOFsplash10-056r-9114500000-80c425a20529e2e7a6ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 20V, Positive-QTOFsplash10-0aor-9024000000-c1bcee3ae9ebe867ecf02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloartenol 40V, Positive-QTOFsplash10-0aor-9182100000-4bbb9a6a3858cc73ce202021-09-23Wishart LabView Spectrum
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 IDFDB015503
KNApSAcK IDC00003650
Chemspider ID83157
KEGG Compound IDC01902
BioCyc IDCYCLOARTENOL
BiGG IDNot Available
Wikipedia LinkCycloartenol
METLIN IDNot Available
PubChem Compound92110
PDB IDNot Available
ChEBI ID17030
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1589871
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:9231356 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.