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Showing Compound Cycloartenol (FDB015503)

Record Information
Version1.0
Creation date2010-04-08 22:11:53 UTC
Update date2020-09-17 15:41:57 UTC
Primary IDFDB015503
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCycloartenol
DescriptionCycloartenol, also known as artosenol or handianol, belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. Cycloartenol is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number469-38-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
9,19-Cyclo-9β-lanost-24-en-3β-olbiospider
9,19-cyclo-9beta-Lanost-24-en-3beta-olHMDB
9,19-Cycloart-24-ene, 3β-olbiospider
9beta,19-cyclolanost-24-en-3beta-olbiospider
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H50O
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
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
Isomeric SMILESCC(CCC=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 84.44%; H 11.81%; O 3.75%DFC
Melting PointMp 99° (solvated)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +54 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCycloartenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-3129500000-84dc7a934204a370748aSpectrum
Predicted GC-MSCycloartenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00lr-4011900000-88cf4a746167f7db19cbSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0003900000-ab3e1619815ddc34b3ae2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1019400000-e52ce1479e1220bb23e32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-2039000000-28a8e4b53c1973a3ebd22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-459890f27580d9795c972016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-280c456ab6df8a80788d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1009400000-74ba59f4db9c4a4d312c2016-08-03View Spectrum
NMRNot Available
ChemSpider ID437607
ChEMBL IDNot Available
KEGG Compound IDC01902
Pubchem Compound ID500213
Pubchem Substance IDNot Available
ChEBI ID17030
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36591
CRC / DFC (Dictionary of Food Compounds) IDJVF95-O:KCW35-L
EAFUS IDNot Available
Dr. Duke IDCYCLOARTENOL
BIGG IDNot Available
KNApSAcK IDC00003650
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCycloartenol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-rheumatic52217 An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
UbiquiotAn antioxidant that protects cells from damage, playing a crucial role in energy production. Therapeutically, it has applications in managing neurodegenerative and cardiovascular diseases, with key medical uses including reducing oxidative stress and improving mitochondrial function.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.