Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:42:10 UTC |
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Updated at | 2021-08-12 19:52:21 UTC |
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NP-MRD ID | NP0002858 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (S)-(-)-Perillic acid |
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Provided By | BMRB |
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Description | (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. (S)-(-)-Perillic acid is found in Perilla frutescens and Spodoptera litura. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid (PMID: 32090266) (PMID: 31945804) (PMID: 31099756) (PMID: 30287506). |
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Structure | CC(=C)[C@H]1CCC(=CC1)C(O)=O InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/t8-/m1/s1 |
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Synonyms | Value | Source |
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(4S)-4-(Prop-1-en-2-yl)cyclohex-1-ene-1-carboxylate | Generator | (S)-(-)-Perillate | Generator |
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Chemical Formula | C10H14O2 |
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Average Mass | 166.2200 Da |
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Monoisotopic Mass | 166.09938 Da |
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IUPAC Name | (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid |
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Traditional Name | (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(=C)[C@H]1CCC(=CC1)C(O)=O |
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InChI Identifier | InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/t8-/m1/s1 |
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InChI Key | CDSMSBUVCWHORP-MRVPVSSYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, ethanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, ethanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, ethanol, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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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 | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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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 | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Jongedijk E, Muller S, van Dijk ADJ, Schijlen E, Champagne A, Boutry M, Levisson M, van der Krol S, Bouwmeester H, Beekwilder J: Novel routes towards bioplastics from plants: elucidation of the methylperillate biosynthesis pathway from Salvia dorisiana trichomes. J Exp Bot. 2020 May 30;71(10):3052-3065. doi: 10.1093/jxb/eraa086. [PubMed:32090266 ]
- Chen C, Luo F, Wu P, Huang Y, Das A, Chen S, Chen J, Hu X, Li F, Fang Z, Zhou S: Metabolomics reveals metabolite changes of patients with pulmonary arterial hypertension in China. J Cell Mol Med. 2020 Feb;24(4):2484-2496. doi: 10.1111/jcmm.14937. Epub 2020 Jan 16. [PubMed:31945804 ]
- Mello CP, Quirico-Santos T, Amorim LF, Silva VG, Fragel LM, Bloom DC, Paixao IP: Perillyl alcohol and perillic acid exert efficient action upon HSV-1 maturation and release of infective virus. Antivir Ther. 2020;25(1):1-11. doi: 10.3851/IMP3315. [PubMed:31099756 ]
- Mukhtar YM, Adu-Frimpong M, Xu X, Yu J: Biochemical significance of limonene and its metabolites: future prospects for designing and developing highly potent anticancer drugs. Biosci Rep. 2018 Nov 13;38(6). pii: BSR20181253. doi: 10.1042/BSR20181253. Print 2018 Dec 21. [PubMed:30287506 ]
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