Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 16:51:26 UTC |
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Updated at | 2022-09-12 16:51:26 UTC |
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NP-MRD ID | NP0330980 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate |
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Description | methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate is found in Mitragyna speciosa. It was first documented in 2020 (PMID: 33408731). Based on a literature review a significant number of articles have been published on Speciogynine (PMID: 33620222) (PMID: 32597657) (PMID: 35468648) (PMID: 35335999) (PMID: 34803709) (PMID: 34467758). |
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Structure | CC[C@H]1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16-,19-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C23H30N2O4 |
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Average Mass | 398.5030 Da |
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Monoisotopic Mass | 398.22056 Da |
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IUPAC Name | methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate |
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Traditional Name | methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | CC[C@H]1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC |
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InChI Identifier | InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16-,19-/m0/s1 |
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InChI Key | LELBFTMXCIIKKX-CYSPOEIOSA-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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Classification | Not classified |
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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 | - Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, Leon F, Sharma A, McMahon LR, Avery BA, McCurdy CR: Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. J Nat Prod. 2021 Apr 23;84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. Epub 2021 Feb 23. [PubMed:33620222 ]
- Flores-Bocanegra L, Raja HA, Graf TN, Augustinovic M, Wallace ED, Hematian S, Kellogg JJ, Todd DA, Cech NB, Oberlies NH: The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids. J Nat Prod. 2020 Jul 24;83(7):2165-2177. doi: 10.1021/acs.jnatprod.0c00257. Epub 2020 Jun 29. [PubMed:32597657 ]
- Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA: Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Apr 25. doi: 10.1055/a-1795-5876. [PubMed:35468648 ]
- Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Effects of Nutrient Fertility on Growth and Alkaloidal Content in Mitragyna speciosa (Kratom). Front Plant Sci. 2020 Dec 21;11:597696. doi: 10.3389/fpls.2020.597696. eCollection 2020. [PubMed:33408731 ]
- Tanna RS, Nguyen JT, Hadi DL, Manwill PK, Flores-Bocanegra L, Layton ME, White JR, Cech NB, Oberlies NH, Rettie AE, Thummel KE, Paine MF: Clinical Pharmacokinetic Assessment of Kratom (Mitragyna speciosa), a Botanical Product with Opioid-like Effects, in Healthy Adult Participants. Pharmaceutics. 2022 Mar 11;14(3). pii: pharmaceutics14030620. doi: 10.3390/pharmaceutics14030620. [PubMed:35335999 ]
- Gutridge AM, Chakraborty S, Varga BR, Rhoda ES, French AR, Blaine AT, Royer QH, Cui H, Yuan J, Cassell RJ, Szabo M, Majumdar S, van Rijn RM: Evaluation of Kratom Opioid Derivatives as Potential Treatment Option for Alcohol Use Disorder. Front Pharmacol. 2021 Nov 3;12:764885. doi: 10.3389/fphar.2021.764885. eCollection 2021. [PubMed:34803709 ]
- Leon F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londono C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR: Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors. J Med Chem. 2021 Sep 23;64(18):13510-13523. doi: 10.1021/acs.jmedchem.1c00726. Epub 2021 Sep 1. [PubMed:34467758 ]
- Hughs M, Kish-Trier E, O'Brien A, McMillin GA: Analysis of Mitragynine and Speciociliatine in Umbilical Cord by LC-MS/MS for Detecting Prenatal Exposure to Kratom. J Anal Toxicol. 2022 Sep 1. pii: 6680066. doi: 10.1093/jat/bkac064. [PubMed:36047661 ]
- Sakamoto J, Kitajima M, Ishikawa H: Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine. Chem Pharm Bull (Tokyo). 2022;70(9):662-668. doi: 10.1248/cpb.c22-00441. [PubMed:36047237 ]
- Karunakaran T, Ngew KZ, Zailan AAD, Mian Jong VY, Abu Bakar MH: The Chemical and Pharmacological Properties of Mitragynine and Its Diastereomers: An Insight Review. Front Pharmacol. 2022 Feb 24;13:805986. doi: 10.3389/fphar.2022.805986. eCollection 2022. [PubMed:35281925 ]
- LOTUS database [Link]
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