Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002388
Secondary Accession Numbers
  • HMDB02388
Metabolite Identification
Common NameBoswellic acid
DescriptionBoswellic acid (BA) is an active component of Boswellia serrata (also known as Salai guggul). Extensive research in the past 30 years identified the active component of this resin as BA (a pentacyclic triterpenic acid) and its derivatives (acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and acetyl-11-keto-beta-boswellic acid). In animal models of inflammation, BA has been shown to be an effective adjuvant mitigating bovine serum albumin-induced arthritis and osteoarthritis. The anti-arthritic potential of BA is a result of its anti-inflammatory activity, mediated through inhibition of NF-kB, COX-2 and 5-LOX. ((PMID: 17475558 , 3429205 ).
Structure
Data?1582752247
Synonyms
ValueSource
BoswellateGenerator
Beta-Boswellic acidHMDB
b-BoswellateHMDB
b-Boswellic acidHMDB
beta-BoswellateHMDB
Β-boswellateHMDB
Β-boswellic acidHMDB
(3alpha,4beta)-3-Hydroxy-urs-12-en-23-OateHMDB
(3alpha,4beta)-3-Hydroxy-urs-12-en-23-Oic acidHMDB
Boswellic acidMeSH
Chemical FormulaC30H48O3
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
IUPAC Name(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-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 Nameboswellic acid
CAS Registry Number631-69-6
SMILES
[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C
InChI Identifier
InChI=1S/C30H48O3/c1-18-10-13-26(3)16-17-28(5)20(24(26)19(18)2)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21-,22-,23-,24+,26-,27-,28-,29-,30-/m1/s1
InChI KeyNBGQZFQREPIKMG-PONOSELZSA-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
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point556.02 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0019 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.105 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00049 g/LALOGPS
logP6.46ALOGPS
logP6.58ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.7 m³·mol⁻¹ChemAxon
Polarizability54.61 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
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]-241.11730932474
DeepCCS[M+Na]+215.23230932474
AllCCS[M+H]+214.632859911
AllCCS[M+H-H2O]+212.932859911
AllCCS[M+NH4]+216.232859911
AllCCS[M+Na]+216.632859911
AllCCS[M-H]-210.532859911
AllCCS[M+Na-2H]-212.532859911
AllCCS[M+HCOO]-214.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Boswellic acid[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C3348.9Standard polar33892256
Boswellic acid[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C3578.7Standard non polar33892256
Boswellic acid[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)[C@](C)(C(O)=O)[C@]3([H])CC[C@@]12C3714.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Boswellic acid,1TMS,isomer #1C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(C(=O)O)[C@@H]5CC[C@]43C)[C@H]123736.7Semi standard non polar33892256
Boswellic acid,1TMS,isomer #2C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O)[C@](C)(C(=O)O[Si](C)(C)C)[C@@H]5CC[C@]43C)[C@H]123635.8Semi standard non polar33892256
Boswellic acid,2TMS,isomer #1C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C)[C@](C)(C(=O)O[Si](C)(C)C)[C@@H]5CC[C@]43C)[C@H]123627.9Semi standard non polar33892256
Boswellic acid,1TBDMS,isomer #1C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(C(=O)O)[C@@H]5CC[C@]43C)[C@H]123947.8Semi standard non polar33892256
Boswellic acid,1TBDMS,isomer #2C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O)[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]5CC[C@]43C)[C@H]123878.0Semi standard non polar33892256
Boswellic acid,2TBDMS,isomer #1C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@@H]5CC[C@]43C)[C@H]124093.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Boswellic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-0016900000-cb1fff7abe55a1dd8af12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Boswellic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0079-0001090000-29382f1137bc882ff7de2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Boswellic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 10V, Positive-QTOFsplash10-052r-0001900000-5f56da065bc22b969e5c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 20V, Positive-QTOFsplash10-007c-0113900000-5a83e20505c6e30ef7a22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 40V, Positive-QTOFsplash10-0fbc-1359400000-9b9b04c9978166488cc42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 10V, Negative-QTOFsplash10-0a4i-0001900000-3722e3ab3a029dc8239f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 20V, Negative-QTOFsplash10-08fu-0003900000-b0303acdec9d0e2b61f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 40V, Negative-QTOFsplash10-0002-2009700000-c61e5c0e2bc4509cc9b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 10V, Positive-QTOFsplash10-0a4i-0001900000-eb5257b1221d22ff985d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 20V, Positive-QTOFsplash10-0a4r-0592700000-abb827ae249d60f701d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 40V, Positive-QTOFsplash10-053i-0941000000-3faa6c5273902337153b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 20V, Negative-QTOFsplash10-0a4i-0001900000-26cad7be7653ea39ced62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Boswellic acid 40V, Negative-QTOFsplash10-0ab9-9001700000-0e9c08294cc3ee118eb72021-09-22Wishart 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 IDFDB112207
KNApSAcK IDC00036795
Chemspider ID147762
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBoswellic acid
METLIN IDNot Available
PubChem Compound168928
PDB IDNot Available
ChEBI ID499685
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1663791
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Khanna D, Sethi G, Ahn KS, Pandey MK, Kunnumakkara AB, Sung B, Aggarwal A, Aggarwal BB: Natural products as a gold mine for arthritis treatment. Curr Opin Pharmacol. 2007 Jun;7(3):344-51. Epub 2007 May 1. [PubMed:17475558 ]
  2. Reddy GK, Dhar SC: Effect of a new non-steroidal anti-inflammatory agent on lysosomal stability in adjuvant induced arthritis. Ital J Biochem. 1987 Jul-Aug;36(4):205-17. [PubMed:3429205 ]