| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 17:23:15 UTC |
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| Updated at | 2022-04-28 17:23:15 UTC |
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| NP-MRD ID | NP0071999 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Camaric acid |
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| Description | Camaric 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). |
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| Structure | 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=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 |
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| Synonyms | | Value | Source |
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| Camarate | Generator |
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| Chemical Formula | C35H52O6 |
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| Average Mass | 568.7950 Da |
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| Monoisotopic Mass | 568.37639 Da |
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| 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 |
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| 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 |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | RSKOPEQHBSFOLQ-OTHZFUNLSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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