| Record Information |
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| Version | 2.0 |
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| Created at | 2022-06-29 21:24:27 UTC |
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| Updated at | 2026-02-20 16:01:15 UTC |
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| NP-MRD ID | NP0140322 |
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| Natural Product DOI | https://doi.org/10.57994/7809 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Antirhine |
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| Description | Antirhine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Antirhine is found in Alstonia angustifolia, Aspidosperma marcgravianum, Rhazya stricta, Strychnos angolensis, Strychnos camptoneura, Strychnos potatorum and Tabernaemontana corymbosa. Antirhine was first documented in 2020 (PMID: 32141756). Based on a literature review a small amount of articles have been published on Antirhine (PMID: 33610704) (PMID: 35209210) (PMID: 33647204) (PMID: 32083463) (PMID: 41705407). |
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| Structure | OC[C@H](C=C)[C@H]1CCN2CCC3=C(NC4=CC=CC=C34)[C@@H]2C1 InChI=1S/C19H24N2O/c1-2-13(12-22)14-7-9-21-10-8-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14/h2-6,13-14,18,20,22H,1,7-12H2/t13-,14-,18-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C19H24N2O |
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| Average Mass | 296.4140 Da |
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| Monoisotopic Mass | 296.18886 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 | OC[C@H](C=C)[C@H]1CCN2CCC3=C(NC4=CC=CC=C34)[C@@H]2C1 |
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| InChI Identifier | InChI=1S/C19H24N2O/c1-2-13(12-22)14-7-9-21-10-8-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14/h2-6,13-14,18,20,22H,1,7-12H2/t13-,14-,18-/m0/s1 |
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| InChI Key | RYMNVEAAYOFGCI-DEYYWGMASA-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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| | 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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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 300.0, , simulated) | [email protected] | Not Available | Not Available | 2026-02-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75.4, Acetone-d6, simulated) | [email protected] | Not Available | Not Available | 2026-02-20 | View Spectrum |
| | 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 beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Pyridoindoles |
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| Direct Parent | Beta carbolines |
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| Alternative Parents | |
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| Substituents | - Beta-carboline
- Quinolizine
- 3-alkylindole
- Indole
- Aralkylamine
- Piperidine
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Hydrocarbon derivative
- Primary alcohol
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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 | - Fokoua AR, Ndjenda MK 2nd, Kaptue Wuyt A, Tatsinkou Bomba FD, Dongmo AK, Chouna R, Nkeng-Efouet PA, Nguelefack TB: Anticonvulsant effects of the aqueous and methanol extracts from the stem bark of Psychotria camptopus Verdc. (Rubiacaea) in rats. J Ethnopharmacol. 2021 May 23;272:113955. doi: 10.1016/j.jep.2021.113955. Epub 2021 Feb 19. [PubMed:33610704 ]
- Abdul-Hameed ZH, Bawakid NO, Alorfi HS, Sobahi TR, Alburae NA, Abdel-Lateff A, Elbehairi SEI, Alfaifi MY, Alhakamy NA, Alarif WM: Monoterpene Indole Alkaloids from the Aerial Parts of Rhazya stricta Induce Cytotoxicity and Apoptosis in Human Adenocarcinoma Cells. Molecules. 2022 Feb 19;27(4):1422. doi: 10.3390/molecules27041422. [PubMed:35209210 ]
- Park E, Bae C, Cho CG, Cheon CH: A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids. J Org Chem. 2021 Mar 19;86(6):4497-4511. doi: 10.1021/acs.joc.0c02936. Epub 2021 Mar 1. [PubMed:33647204 ]
- Bae C, Park E, Cho CG, Cheon CH: General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers. Org Lett. 2020 Mar 20;22(6):2354-2358. doi: 10.1021/acs.orglett.0c00544. Epub 2020 Mar 6. [PubMed:32141756 ]
- Nakabayashi R, Mori T, Takeda N, Toyooka K, Sudo H, Tsugawa H, Saito K: Metabolomics with (15)N Labeling for Characterizing Missing Monoterpene Indole Alkaloids in Plants. Anal Chem. 2020 Apr 21;92(8):5670-5675. doi: 10.1021/acs.analchem.9b03860. Epub 2020 Feb 21. [PubMed:32083463 ]
- Kasbekar DP: The fun we had doing crosses with Neurospora wild and Dp strains. J Genet. 2026;105:01. [PubMed:41705407 ]
- DOI: 10.1016/s0040-4020(01)85357-6
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