11-Keto-beta-boswellic acid (CHEM030331)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:49:36 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030331
Identification
Common Name11-Keto-beta-boswellic acid
ClassSmall Molecule
Description11-Keto-beta-boswellic acid is found in herbs and spices. 11-Keto-beta-boswellic acid is a constituent of Boswellia serrata (Indian olibanum).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Keto-b-boswellateGenerator
11-Keto-b-boswellic acidGenerator
11-Keto-beta-boswellateGenerator
11-Keto-β-boswellateGenerator
11-Keto-β-boswellic acidGenerator
11-Keto-boswellic acidMeSH
11-oxo-b-Boswellic acidHMDB
3-Hydroxy-11-oxo-(3alpha,4beta)-urs-12-en-23-Oic acidHMDB
3a-Hydroxy-11-oxo-12-ursen-24-Oic acidHMDB
Urs-12-en-24-Oic acid, 3alpha-hydroxy-11-oxo- (8ci)HMDB
Chemical FormulaC30H46O4
Average Molecular Mass470.684 g/mol
Monoisotopic Mass470.340 g/mol
CAS Registry Number17019-92-0
IUPAC Name(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid
Traditional Name(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
SMILES[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C
InChI IdentifierInChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1
InChI KeyYIMHGPSYDOGBPI-YZCVQEKWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Beta-hydroxy acid
  • Cyclohexenone
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0015 g/LALOGPS
logP5.5ALOGPS
logP6.02ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.34 m³·mol⁻¹ChemAxon
Polarizability54.73 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0106900000-4a42f2be2f089484b4d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f72-0000292000-293eba24cc86c4b22e5bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-0f08e0a7b369ffe41661Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-1200900000-9e7608df553a11ac163aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3827900000-0211a0626c3744833989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-3f1fe05e64c9a9e4be63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r0-0000900000-10512f6eb97d6ca03b11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1010900000-0d7eaf51793f77099810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-d60788820b8857f5a5d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0000900000-1fb71433741631d6e099Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2000900000-cf1e91907af44e00699eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-5ef53f7b9260889fda76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-0200900000-76e2a060e370e56bf80dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05e9-6920300000-0f5d20e71ca8922d6703Spectrum
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 IDHMDB0036671
FooDB IDFDB015601
Phenol Explorer IDNot Available
KNApSAcK IDC00042045
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8023261
ChEBI IDNot Available
PubChem Compound ID9847548
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. 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.
3. 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.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM