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Record Information
Version2.0
Created at2022-04-28 17:23:15 UTC
Updated at2022-04-28 17:23:15 UTC
NP-MRD IDNP0071999
Secondary Accession NumbersNone
Natural Product Identification
Common NameCamaric acid
DescriptionCamaric acid, also known as camarate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Camaric acid is found in Lantana camara , Lantana montevidensis, Lippia turbinata and Tilesia baccata. Camaric acid was first documented in 2003 (PMID: 12576645). Based on a literature review a significant number of articles have been published on Camaric acid (PMID: 33848915) (PMID: 30675937) (PMID: 24827681) (PMID: 18816515) (PMID: 18807381) (PMID: 16010828).
Structure
Thumb
Synonyms
ValueSource
CamarateGenerator
Chemical FormulaC35H52O6
Average Mass568.7950 Da
Monoisotopic Mass568.37639 Da
IUPAC Name(1S,2S,6S,10R,11S,14S,15R,18R,20S)-20-hydroxy-8,8,14,15,19,19-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid
Traditional Name(1S,2S,6S,10R,11S,14S,15R,18R,20S)-20-hydroxy-8,8,14,15,19,19-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-21-oxahexacyclo[18.2.2.0^{1,18}.0^{2,15}.0^{5,14}.0^{6,11}]tetracos-4-ene-11-carboxylic acid
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)O[C@@H]1CC(C)(C)C[C@H]2C3=CC[C@H]4[C@@](C)(CC[C@H]5C(C)(C)[C@]6(O)CC[C@]45CO6)[C@]3(C)CC[C@@]12C(O)=O
InChI Identifier
InChI=1S/C35H52O6/c1-9-21(2)27(36)41-26-19-29(3,4)18-23-22-10-11-25-32(8,31(22,7)14-16-34(23,26)28(37)38)13-12-24-30(5,6)35(39)17-15-33(24,25)20-40-35/h9-10,23-26,39H,11-20H2,1-8H3,(H,37,38)/b21-9-/t23-,24-,25-,26+,31+,32+,33+,34-,35-/m0/s1
InChI KeyRSKOPEQHBSFOLQ-OTHZFUNLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lantana camaraPlant
Lantana montevidensisLOTUS Database
Lippia turbinataPlant
Tilesia baccataLOTUS Database
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
  • Naphthopyran
  • Naphthalene
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Oxane
  • Pyran
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.08ALOGPS
logP7.04ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity158.81 m³·mol⁻¹ChemAxon
Polarizability65.98 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00031646
Chemspider ID28425586
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCamarate
METLIN IDNot Available
PubChem Compound91895465
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Delgado-Altamirano R, Garcia-Aguilera ME, Delgado-Dominguez J, Becker I, Rodriguez de San Miguel E, Rojas-Molina A, Esturau-Escofet N: (1)H NMR profiling and chemometric analysis as an approach to predict the leishmanicidal activity of dichloromethane extracts from Lantana camara (L.). J Pharm Biomed Anal. 2021 May 30;199:114060. doi: 10.1016/j.jpba.2021.114060. Epub 2021 Apr 3. [PubMed:33848915 ]
  2. Delgado-Altamirano R, Rojas A, Esturau-Escofet N: (1) H and (13) C NMR reassignment of some chemical shifts of lantanilic acid and camaric acid. Magn Reson Chem. 2019 Jun;57(6):320-325. doi: 10.1002/mrc.4839. Epub 2019 Feb 19. [PubMed:30675937 ]
  3. Begum S, Ayub A, Qamar Zehra S, Shaheen Siddiqui B, Iqbal Choudhary M, Samreen: Leishmanicidal Triterpenes from Lantana camara. Chem Biodivers. 2014 May;11(5):709-18. doi: 10.1002/cbdv.201300151. [PubMed:24827681 ]
  4. Begum S, Zehra SQ, Siddiqui BS, Fayyaz S, Ramzan M: Pentacyclic triterpenoids from the aerial parts of Lantana camara and their nematicidal activity. Chem Biodivers. 2008 Sep;5(9):1856-66. doi: 10.1002/cbdv.200890173. [PubMed:18816515 ]
  5. Begum S, Wahab A, Siddiqui BS: Pentacyclic triterpenoids from the aerial parts of Lantana camara. Chem Pharm Bull (Tokyo). 2003 Feb;51(2):134-7. doi: 10.1248/cpb.51.134. [PubMed:12576645 ]
  6. Innocent E, Joseph CC, Gikonyo NK, Moshi MJ, Nkunya MH, Hassanali A: Mosquito larvicidal constituents from Lantana viburnoides sp viburnoides var kisi (A. rich) Verdc (Verbenaceae). J Vector Borne Dis. 2008 Sep;45(3):240-4. [PubMed:18807381 ]
  7. Qamar F, Begum S, Raza SM, Wahab A, Siddiqui BS: Nematicidal natural products from the aerial parts of Lantana camara Linn. Nat Prod Res. 2005 Sep;19(6):609-13. doi: 10.1080/14786410512331330594. [PubMed:16010828 ]
  8. Okunade AL, Lewis WH: Oleanene constituents of Lantana cujabensis. Fitoterapia. 2004 Jun;75(3-4):327-31. doi: 10.1016/j.fitote.2004.02.005. [PubMed:15158990 ]