24-Methylenecycloartan-3-ol (CHEM029605)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:16:43 UTC
Update Date2016-11-09 01:18:55 UTC
Accession NumberCHEM029605
Identification
Common Name24-Methylenecycloartan-3-ol
ClassSmall Molecule
DescriptionA pentacyclic triterpenoid that is (9beta)-24-methylene-9,19-cyclolanostane which carries a hydroxy group at position 3beta. It is isolated from several plant species including Euphorbia, Epidendrum, Psychotria and Sideritis.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,9beta)-24-Methylene-9,19-cyclolanostan-3-olChEBI
24(28)-MethylenecycloartanolChEBI
24-Methylene cycloartanolChEBI
24-Methylene-9beta,19-cyclo-lanostan-3beta-olChEBI
24-Methylene-cycloartanolChEBI
24-Methylenecycloartan-3beta-olChEBI
4alpha,4beta,14alpha-Trimethyl-9beta,19-cyclo-5alpha-ergost-24(24(1))-en-3beta-olKegg
(3b,9b)-24-Methylene-9,19-cyclolanostan-3-olGenerator
(3Β,9β)-24-methylene-9,19-cyclolanostan-3-olGenerator
24-Methylene-9b,19-cyclo-lanostan-3b-olGenerator
24-Methylene-9β,19-cyclo-lanostan-3β-olGenerator
24-Methylenecycloartan-3b-olGenerator
24-Methylenecycloartan-3β-olGenerator
4a,4b,14a-Trimethyl-9b,19-cyclo-5a-ergost-24(24(1))-en-3b-olGenerator
4Α,4β,14α-trimethyl-9β,19-cyclo-5α-ergost-24(24(1))-en-3β-olGenerator
24-MethylenecycloartanolChEMBL, KEGG
(3beta)-24-Methylene-9,19-cyclolanostan-3-olPhytoBank
(3β)-24-Methylene-9,19-cyclolanostan-3-olPhytoBank
24-Methylencycloartan-3beta-olPhytoBank
24-Methylencycloartan-3β-olPhytoBank
24-Methylene-9,19-cyclolanostan-3beta-olPhytoBank
24-Methylene-9,19-cyclolanostan-3β-olPhytoBank
24-MethylidenecycloartanolPhytoBank
3beta-Hydroxy-24-methylenecycloartanePhytoBank
3β-Hydroxy-24-methylenecycloartanePhytoBank
9,19-Cyclo-24-methylenelanostan-3beta-olPhytoBank
9,19-Cyclo-24-methylenelanostan-3β-olPhytoBank
24-MethylenecycloartenolPhytoBank
Chemical FormulaC31H52O
Average Molecular Mass440.744 g/mol
Monoisotopic Mass440.402 g/mol
CAS Registry Number1449-09-8
IUPAC Name(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
Traditional Name(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol
SMILES[H][C@@]12CC[C@]3([H])[C@]4(C[C@@]14CC[C@]1(C)[C@H](CC[C@@]21C)[C@H](C)CCC(=C)C(C)C)CC[C@H](O)C3(C)C
InChI IdentifierInChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-26,32H,3,9-19H2,1-2,4-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+/m1/s1
InChI KeyBDHQMRXFDYJGII-UEBIAWITSA-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
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 Solubility0.00013 g/LALOGPS
logP6.52ALOGPS
logP7.89ChemAxon
logS-6.5ALOGPS
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 Count5ChemAxon
Refractivity135.51 m³·mol⁻¹ChemAxon
Polarizability56.66 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 (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-1002900000-dc4ed5c79a069da3732aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008i-5019300000-947794778cdfe71a9644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9166200000-73426bc629015a0e8428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-8f7e62e6454bfee79882Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-ca977cb95b263608c3c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2004900000-60994fd38d57d5e18d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-6abf4200d93b5ca719d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-6abf4200d93b5ca719d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0000900000-a884e492357f1761eea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-9115400000-32e71dc0bce1810b6695Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-9113000000-b400f27bffc70c0a5115Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-9251000000-df458928f3274672744dSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-7920100000-1b1e8b1948c5f53e3b9bSpectrum
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 IDHMDB0303481
FooDB IDFDB014438
Phenol Explorer IDNot Available
KNApSAcK IDC00003661
BiGG IDNot Available
BioCyc IDCPD-696
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID85017
ChEBI ID1307
PubChem Compound ID94204
Kegg Compound IDC08830
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10691725
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=13573499
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14622971
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17265335
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17337022
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17691046
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28480734
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=4651646