3alpha-Acetoxy-11-keto-beta-boswellic acid (CHEM030332)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:49:38 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030332
Identification
Common Name3alpha-Acetoxy-11-keto-beta-boswellic acid
ClassSmall Molecule
Description3alpha-Acetoxy-11-keto-beta-boswellic acid is found in herbs and spices. 3alpha-Acetoxy-11-keto-beta-boswellic acid is isolated from Boswellia serrata (Indian olibanum).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3a-Acetoxy-11-keto-b-boswellateGenerator
3a-Acetoxy-11-keto-b-boswellic acidGenerator
3alpha-Acetoxy-11-keto-beta-boswellateGenerator
3Α-acetoxy-11-keto-β-boswellateGenerator
3Α-acetoxy-11-keto-β-boswellic acidGenerator
(3R,4R,6AR,6BS,8ar,11R,12S,12ar,14BS)-3-(acetyloxy)-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-carboxylateHMDB
Chemical FormulaC32H48O5
Average Molecular Mass512.721 g/mol
Monoisotopic Mass512.350 g/mol
CAS Registry Number67416-61-9
IUPAC Name(3R,4R,6aR,6bS,8aR,11R,12S,12aR,14bS)-3-(acetyloxy)-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,6aR,6bS,8aR,11R,12S,12aR,14bS)-3-(acetyloxy)-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
SMILESC[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC(=O)C4[C@@]5(C)CC[C@@H](OC(C)=O)[C@@](C)(C5CC[C@@]34C)C(O)=O)[C@@H]2[C@H]1C
InChI IdentifierInChI=1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23?,24-,25+,26?,28-,29+,30-,31-,32-/m1/s1
InChI KeyHMMGKOVEOFBCAU-MFIYSICPSA-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
  • Cyclohexenone
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen 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 Solubility0.00045 g/LALOGPS
logP5.9ALOGPS
logP6.46ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity143.49 m³·mol⁻¹ChemAxon
Polarizability59.04 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-00l2-1023900000-374d4281e388c097f69eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-3013190000-33293c5dcf5addaa6cddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ka-0000930000-aee9a09e734930cdc2adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-106r-0001900000-ac630e78d09d716bdde9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-2302900000-c09d590b534a16c5d2e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-1000950000-649eb66990ff8e87c64dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-1000900000-aab9e0f247c95f354882Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i3-3000900000-2d2a516b49879d166336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000390000-1b9c1118e9cd9593984fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-0011950000-f4ab437a36afa218e1f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-5971410000-5b078bbadfbaab5d9206Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000020000-f3b15eadb33448823e1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000040000-e377c5bb703d0def9d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000050000-0c34dd8f0390270221b6Spectrum
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 IDHMDB0036672
FooDB IDFDB015602
Phenol Explorer IDNot Available
KNApSAcK IDC00054337
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24022866
ChEBI IDNot Available
PubChem Compound ID45359902
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