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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:50:17 UTC
Update Date2022-03-07 02:55:01 UTC
HMDB IDHMDB0036672
Secondary Accession Numbers
  • HMDB36672
Metabolite Identification
Common Name3alpha-Acetoxy-11-keto-beta-boswellic acid
Description3alpha-Acetoxy-11-keto-beta-boswellic acid, also known as 3α-acetoxy-11-keto-β-boswellate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on 3alpha-Acetoxy-11-keto-beta-boswellic acid.
Structure
Data?1563862907
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 Weight512.7205
Monoisotopic Molecular Weight512.350174646
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
CAS Registry Number67416-61-9
SMILES
C[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 Identifier
InChI=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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point271 °CNot Available
Boiling Point600.29 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00028 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.418 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-252.36630932474
DeepCCS[M+Na]+226.50530932474
AllCCS[M+H]+223.532859911
AllCCS[M+H-H2O]+222.132859911
AllCCS[M+NH4]+224.832859911
AllCCS[M+Na]+225.232859911
AllCCS[M-H]-217.632859911
AllCCS[M+Na-2H]-220.132859911
AllCCS[M+HCOO]-223.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3alpha-Acetoxy-11-keto-beta-boswellic acidC[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]1C4441.9Standard polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acidC[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]1C3521.1Standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acidC[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]1C4047.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3alpha-Acetoxy-11-keto-beta-boswellic acid,1TMS,isomer #1CC(=O)O[C@@H]1CC[C@@]2(C)C(CC[C@]3(C)C2C(=O)C=C2[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC[C@]23C)[C@@]1(C)C(=O)O[Si](C)(C)C3919.3Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,1TMS,isomer #2CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O3866.4Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,2TMS,isomer #1CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O[Si](C)(C)C3724.5Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,2TMS,isomer #1CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O[Si](C)(C)C3703.1Standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,1TBDMS,isomer #1CC(=O)O[C@@H]1CC[C@@]2(C)C(CC[C@]3(C)C2C(=O)C=C2[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC[C@]23C)[C@@]1(C)C(=O)O[Si](C)(C)C(C)(C)C4145.9Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,1TBDMS,isomer #2CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O4097.5Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,2TBDMS,isomer #1CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O[Si](C)(C)C(C)(C)C4156.3Semi standard non polar33892256
3alpha-Acetoxy-11-keto-beta-boswellic acid,2TBDMS,isomer #1CC(=O)O[C@@H]1CC[C@]2(C)C3=C(O[Si](C)(C)C(C)(C)C)C=C4[C@@H]5[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CCC2[C@@]1(C)C(=O)O[Si](C)(C)C(C)(C)C4184.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00l2-1023900000-374d4281e388c097f69e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-3013190000-33293c5dcf5addaa6cdd2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 10V, Negative-QTOFsplash10-02t9-1000950000-649eb66990ff8e87c64d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 20V, Negative-QTOFsplash10-066r-1000900000-aab9e0f247c95f3548822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 40V, Negative-QTOFsplash10-05i3-3000900000-2d2a516b49879d1663362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 10V, Negative-QTOFsplash10-0a4i-9000020000-f3b15eadb33448823e1e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 20V, Negative-QTOFsplash10-0a4i-9000040000-e377c5bb703d0def9d492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 40V, Negative-QTOFsplash10-0a4i-9000050000-0c34dd8f0390270221b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 10V, Positive-QTOFsplash10-03ka-0000930000-aee9a09e734930cdc2ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 20V, Positive-QTOFsplash10-106r-0001900000-ac630e78d09d716bdde92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 40V, Positive-QTOFsplash10-0a4r-2302900000-c09d590b534a16c5d2e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 10V, Positive-QTOFsplash10-03di-0000390000-1b9c1118e9cd9593984f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 20V, Positive-QTOFsplash10-08fr-0011950000-f4ab437a36afa218e1f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Acetoxy-11-keto-beta-boswellic acid 40V, Positive-QTOFsplash10-01ox-5971410000-5b078bbadfbaab5d92062021-09-24Wishart 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 IDFDB015602
KNApSAcK IDC00054337
Chemspider ID24022866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45359902
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1664541
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.