Record Information |
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Version | 1.0 |
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Created at | 2022-09-04 13:12:02 UTC |
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Updated at | 2022-09-04 13:12:02 UTC |
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NP-MRD ID | NP0195351 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,12b,13,14b-decahydro-2h-picene-4a-carboxylic acid |
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Description | Fupenzic acid, also known as fupenzate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,12b,13,14b-decahydro-2h-picene-4a-carboxylic acid is found in Rosa rugosa, Rubus chingii and Rubus irenaeus. It was first documented in 2013 (PMID: 23772756). Based on a literature review a significant number of articles have been published on Fupenzic acid (PMID: 30717534) (PMID: 29318764) (PMID: 27478101) (PMID: 25911815) (PMID: 34923054). |
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Structure | C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C=C(O)C(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O InChI=1S/C30H44O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,16-17,20-22,31,35H,9-15H2,1-7H3,(H,33,34)/t17-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1 |
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Synonyms | Value | Source |
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Fupenzate | Generator |
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Chemical Formula | C30H44O5 |
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Average Mass | 484.6770 Da |
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Monoisotopic Mass | 484.31887 Da |
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IUPAC Name | (1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,12b,13,14b-octadecahydropicene-4a-carboxylic acid |
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Traditional Name | (1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,12b,13,14b-decahydro-2H-picene-4a-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C=C(O)C(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O |
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InChI Identifier | InChI=1S/C30H44O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,16-17,20-22,31,35H,9-15H2,1-7H3,(H,33,34)/t17-,20+,21-,22-,26+,27-,28-,29-,30+/m1/s1 |
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InChI Key | FMTPULGTIHBJRT-BBRBLNSOSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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
- Cyclohexenone
- Cyclic alcohol
- Tertiary alcohol
- Ketone
- Cyclic ketone
- Carboxylic acid derivative
- Carboxylic acid
- Enol
- Monocarboxylic acid or derivatives
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | - Zhou BD, Zhang XL, Niu HY, Guan CY, Liu YP, Fu YH: [Chemical constituents from stems and leaves of Psychotria serpens]. Zhongguo Zhong Yao Za Zhi. 2018 Dec;43(24):4878-4883. doi: 10.19540/j.cnki.cjcmm.20180912.003. [PubMed:30717534 ]
- Zhang X, Zhou Y, Wei Z, Shen J, Wang L, Ma Z, Zhang X: Antiphytoviral toxins of Actinidia chinensis root bark (ACRB) extract: laboratory and semi-field trials. Pest Manag Sci. 2018 Jul;74(7):1630-1636. doi: 10.1002/ps.4854. Epub 2018 Feb 23. [PubMed:29318764 ]
- Zhang X, Zhu ZX, Wang J, Yang WQ, Su C, Li J, Zhang Y, Zheng J, Shi SP, Tu PF: Triterpenoids from the roots of Rubus parvifolius. Chin J Nat Med. 2016 May;14(5):377-81. doi: 10.3724/SP.J.1009.2016.00377. [PubMed:27478101 ]
- Huang XY, Ma GX, Zhong XQ, Zhou YL, Dai HN, Wu HF, Zhu YD, Yang JS, Yuan JQ, Xu XD: [Triterpene constituents from Rosa cymosa Tratt]. Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(23):4637-41. [PubMed:25911815 ]
- Zhang J, Yang YN, Feng ZM, Yuan X, Zhang X, Jiang JS, Zhang PC: The triterpenoids and sesquiterpenoids from the plant of Agrimonia pilosa. Fitoterapia. 2022 Mar;157:105104. doi: 10.1016/j.fitote.2021.105104. Epub 2021 Dec 16. [PubMed:34923054 ]
- Song NY, Cho JG, Im D, Lee DY, Wu Q, Seo WD, Kang HC, Lee YH, Baek NI: Triterpenoids from Fragaria ananassa calyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells. Nat Prod Res. 2013;27(23):2219-23. doi: 10.1080/14786419.2013.805330. Epub 2013 Jun 18. [PubMed:23772756 ]
- LOTUS database [Link]
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