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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:41:02 UTC
Update Date2022-07-12 15:36:37 UTC
HMDB IDHMDB0041043
Secondary Accession Numbers
  • HMDB41043
Metabolite Identification
Common Name3alpha-Corosolic acid
Description3-alpha-Corosolic acid, also known as 3-a-corosolate or simply corosolic acid, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Corosolic acid (CA), is a natural pentacyclic triterpenoid acid isolated from Lagerstroemia sp. (Banaba). Banaba, or Lagerstroemia speciosa, is a tree native to tropical Southeast Asia. It is also known as Crape Myrtle. The tree is widely distributed in India, Malaysia, and the Philippines, where it’s known as Jarul, Pride of India, or Giant Crape Myrtle. Almost every part of the tree offers medicinal properties. For example, the bark is often used to treat diarrhea, while its root and fruit extracts are believed to have an analgesic, or pain-relieving, effect. The most important compound, 3-alpha-Corosolic acid, is found in the leaves and possesses antiatherosclerotic, antihyperlipidemic, antioxidant, anti-inflammatory, antidiabetic, antifungal, antiviral, and antineoplastic activities (PMID: 26615974 ). The effects of CA are thought to be mediated by peroxisome proliferator activator receptor (PPAR), mitogen-activated protein kinase (MAPK), NF-κB, and other signal transduction factors. Banaba extracts that include Corosolic acid have been used for many years in folk medicine to treat diabetes, with the first published research study being reported in 1940. The beneficial effects of corosolic acid with regard to glucose and lipid metabolism appear to involve multiple mechanisms, including enhanced cellular uptake of glucose, impaired hydrolysis of sucrose and starches, decreased gluconeogenesis and improved regulation of lipid metabolism (PMID: 22095937 ). 3-alpha-Corosolic acid is only found in those individuals who consume this folk medicine or eat the plant. Technically 3-alpha-Corosolic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults or impacts from environmental, dietary and occupational sources.
Structure
Data?1563863617
Synonyms
ValueSource
3a-CorosolateGenerator
3a-Corosolic acidGenerator
3alpha-CorosolateGenerator
3Α-corosolateGenerator
3Α-corosolic acidGenerator
2,3-Dihydroxy-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-carboxylateHMDB
(2a,3a)-Dihydroxy-12-ursen-24-OateHMDB
Chemical FormulaC30H48O4
Average Molecular Weight472.6997
Monoisotopic Molecular Weight472.355260024
IUPAC Name2,3-dihydroxy-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 Name2,3-dihydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid
CAS Registry Number164920-64-3
SMILES
CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1C
InChI Identifier
InChI=1S/C30H48O4/c1-17-10-12-26(3)14-15-28(5)19(23(26)18(17)2)8-9-21-27(4)16-20(31)24(32)30(7,25(33)34)22(27)11-13-29(21,28)6/h8,17-18,20-24,31-32H,9-16H2,1-7H3,(H,33,34)
InChI KeyCAQINDLNYJDVHH-UHFFFAOYSA-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
  • 12-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP6.05ALOGPS
logP5.51ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity135.06 m³·mol⁻¹ChemAxon
Polarizability56.3 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
DarkChem[M+H]+209.62631661259
DarkChem[M-H]-203.96531661259
DeepCCS[M-2H]-249.33630932474
DeepCCS[M+Na]+224.79230932474
AllCCS[M+H]+216.932859911
AllCCS[M+H-H2O]+215.232859911
AllCCS[M+NH4]+218.432859911
AllCCS[M+Na]+218.832859911
AllCCS[M-H]-212.232859911
AllCCS[M+Na-2H]-214.432859911
AllCCS[M+HCOO]-216.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3alpha-Corosolic acidCC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1C3220.1Standard polar33892256
3alpha-Corosolic acidCC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1C3492.5Standard non polar33892256
3alpha-Corosolic acidCC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(O)=O)C2C1C3916.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3alpha-Corosolic acid,1TMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C1C3986.4Semi standard non polar33892256
3alpha-Corosolic acid,1TMS,isomer #2CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C1C3979.0Semi standard non polar33892256
3alpha-Corosolic acid,1TMS,isomer #3CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C1C3892.9Semi standard non polar33892256
3alpha-Corosolic acid,2TMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C1C4017.2Semi standard non polar33892256
3alpha-Corosolic acid,2TMS,isomer #2CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C1C3893.5Semi standard non polar33892256
3alpha-Corosolic acid,2TMS,isomer #3CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C1C3871.2Semi standard non polar33892256
3alpha-Corosolic acid,3TMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)(C(=O)O[Si](C)(C)C)C5CCC43C)C2C1C3879.1Semi standard non polar33892256
3alpha-Corosolic acid,1TBDMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O)C5CCC43C)C2C1C4208.8Semi standard non polar33892256
3alpha-Corosolic acid,1TBDMS,isomer #2CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C1C4204.7Semi standard non polar33892256
3alpha-Corosolic acid,1TBDMS,isomer #3CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C1C4134.8Semi standard non polar33892256
3alpha-Corosolic acid,2TBDMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O)C5CCC43C)C2C1C4454.6Semi standard non polar33892256
3alpha-Corosolic acid,2TBDMS,isomer #2CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C1C4357.0Semi standard non polar33892256
3alpha-Corosolic acid,2TBDMS,isomer #3CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C1C4346.6Semi standard non polar33892256
3alpha-Corosolic acid,3TBDMS,isomer #1CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)(C(=O)O[Si](C)(C)C(C)(C)C)C5CCC43C)C2C1C4555.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha-Corosolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-0007900000-fe685c23d9ac8f941bdf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha-Corosolic 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 - 3alpha-Corosolic acid 10V, Negative-QTOFsplash10-00di-0000900000-e5e324608a7867f769c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 20V, Negative-QTOFsplash10-05di-0000900000-bb7fb1917515c8853d662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 40V, Negative-QTOFsplash10-08fr-2002900000-700491bb2932b616ac782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 10V, Negative-QTOFsplash10-00di-0000900000-ce83f241675374237da42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 20V, Negative-QTOFsplash10-00fr-0000900000-8b0be4290c548ecb72bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 40V, Negative-QTOFsplash10-00xr-4000900000-0aac381418b213dec2112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 10V, Positive-QTOFsplash10-0ab9-0000900000-2a22135a436a594fac5f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 20V, Positive-QTOFsplash10-0a4r-0010900000-75042ab299a86de7ed542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 40V, Positive-QTOFsplash10-0a4r-2466900000-d66d98bf3a0e855dc8ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 10V, Positive-QTOFsplash10-00di-0000900000-fe355ccc18f5205fbd352021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 20V, Positive-QTOFsplash10-0ab9-4193800000-84474b45a79baf9a48802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha-Corosolic acid 40V, Positive-QTOFsplash10-0ab9-3893100000-bd3d2e372d03970ff4ec2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB020916
KNApSAcK IDNot Available
Chemspider ID16161158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23132198
PDB IDNot Available
ChEBI ID175734
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. Kim SJ, Cha JY, Kang HS, Lee JH, Lee JY, Park JH, Bae JH, Song DK, Im SS: Corosolic acid ameliorates acute inflammation through inhibition of IRAK-1 phosphorylation in macrophages. BMB Rep. 2016 May;49(5):276-81. doi: 10.5483/bmbrep.2016.49.5.241. [PubMed:26615974 ]
  6. Stohs SJ, Miller H, Kaats GR: A review of the efficacy and safety of banaba (Lagerstroemia speciosa L.) and corosolic acid. Phytother Res. 2012 Mar;26(3):317-24. doi: 10.1002/ptr.3664. Epub 2011 Nov 17. [PubMed:22095937 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.