Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 07:33:09 UTC |
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Updated at | 2022-09-12 07:33:10 UTC |
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NP-MRD ID | NP0326200 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2,3,6-trihydroxy-2,6-dimethyloct-7-enoate |
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Description | Rhinacanthin L belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl 2,3,6-trihydroxy-2,6-dimethyloct-7-enoate is found in Rhinacanthus nasutus. It was first documented in 2018 (PMID: 30583689). Based on a literature review a significant number of articles have been published on Rhinacanthin L (PMID: 33612794) (PMID: 31399508) (PMID: 35631453) (PMID: 29561167). |
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Structure | CC(C)(COC(=O)C(C)(O)C(O)CCC(C)(O)C=C)CC1=C(O)C2=CC=CC=C2C(=O)C1=O InChI=1S/C25H32O8/c1-6-24(4,31)12-11-18(26)25(5,32)22(30)33-14-23(2,3)13-17-19(27)15-9-7-8-10-16(15)20(28)21(17)29/h6-10,18,26-27,31-32H,1,11-14H2,2-5H3 |
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Synonyms | Not Available |
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Chemical Formula | C25H32O8 |
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Average Mass | 460.5230 Da |
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Monoisotopic Mass | 460.20972 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | CC(C)(COC(=O)C(C)(O)C(O)CCC(C)(O)C=C)CC1=C(O)C2=CC=CC=C2C(=O)C1=O |
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InChI Identifier | InChI=1S/C25H32O8/c1-6-24(4,31)12-11-18(26)25(5,32)22(30)33-14-23(2,3)13-17-19(27)15-9-7-8-10-16(15)20(28)21(17)29/h6-10,18,26-27,31-32H,1,11-14H2,2-5H3 |
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InChI Key | WSELFFSWCDFWSR-UHFFFAOYSA-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 naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthoquinones |
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Direct Parent | Naphthoquinones |
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Alternative Parents | |
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Substituents | - Naphthoquinone
- 1-naphthol
- Fatty alcohol
- Aryl ketone
- Quinone
- Beta-hydroxy acid
- Fatty acid ester
- Fatty acyl
- Hydroxy acid
- Monosaccharide
- Vinylogous acid
- Tertiary alcohol
- 1,2-diol
- Carboxylic acid ester
- Cyclic ketone
- Ketone
- Secondary alcohol
- Enol
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic 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 | - Sheikh HM, Reshi NA: Characterisation of secondary metabolites from Rhinacanthus nasutus L (Kurz) for the identification of novel antibacterial leads. Trop Biomed. 2020 Sep 1;37(3):812-821. doi: 10.47665/tb.37.3.812. [PubMed:33612794 ]
- Dunkoksung W, Vardhanabhuti N, Siripong P, Jianmongkol S: Rhinacanthin-C Mediated Herb-Drug Interactions with Drug Transporters and Phase I Drug-Metabolizing Enzymes. Drug Metab Dispos. 2019 Oct;47(10):1040-1049. doi: 10.1124/dmd.118.085647. Epub 2019 Aug 9. [PubMed:31399508 ]
- Rakkhittawattana V, Panichayupakaranant P, Prasanth MI, Brimson JM, Tencomnao T: Rhinacanthin-C but Not -D Extracted from Rhinacanthus nasutus (L.) Kurz Offers Neuroprotection via ERK, CHOP, and LC3B Pathways. Pharmaceuticals (Basel). 2022 May 20;15(5):627. doi: 10.3390/ph15050627. [PubMed:35631453 ]
- Boueroy P, Saensa‑Ard S, Siripong P, Kanthawong S, Hahnvajanawong C: Rhinacanthin-C Extracted from Rhinacanthus nasutus (L.) Inhibits Cholangiocarcinoma Cell Migration and Invasion by Decreasing MMP-2, uPA, FAK and MAPK Pathways. Asian Pac J Cancer Prev. 2018 Dec 25;19(12):3605-3613. doi: 10.31557/APJCP.2018.19.12.3605. [PubMed:30583689 ]
- Ngoc TM, Phuong NTT, Khoi NM, Park S, Kwak HJ, Nhiem NX, Trang BTT, Tai BH, Song JH, Ko HJ, Kim SH: A new naphthoquinone analogue and antiviral constituents from the root of Rhinacanthus nasutus. Nat Prod Res. 2019 Feb;33(3):360-366. doi: 10.1080/14786419.2018.1452004. Epub 2018 Mar 21. [PubMed:29561167 ]
- LOTUS database [Link]
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