Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 01:53:22 UTC |
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Updated at | 2022-09-10 01:53:22 UTC |
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NP-MRD ID | NP0293725 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3z,5r)-3-{[(1s,2r,4ar,8s,8ar)-2-[(2s,3s)-2,3-dimethyloxiran-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-isopropyl-1-methylpyrrolidine-2,4-dione |
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Description | Trichobotrysin B belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (3z,5r)-3-{[(1s,2r,4ar,8s,8ar)-2-[(2s,3s)-2,3-dimethyloxiran-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-isopropyl-1-methylpyrrolidine-2,4-dione is found in Trichobotrys effusa. It was first documented in 2022 (PMID: 36115679). Based on a literature review a significant number of articles have been published on Trichobotrysin B (PMID: 36115676) (PMID: 36115672) (PMID: 36115668) (PMID: 36115655). |
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Structure | CC(C)[C@H]1N(C)C(=O)\C(=C(/O)[C@H]2[C@@H]3[C@@H](C)CCC[C@H]3C=C(C)[C@@H]2[C@]2(C)O[C@H]2C)C1=O InChI=1S/C25H37NO4/c1-12(2)21-23(28)19(24(29)26(21)7)22(27)18-17-13(3)9-8-10-16(17)11-14(4)20(18)25(6)15(5)30-25/h11-13,15-18,20-21,27H,8-10H2,1-7H3/b22-19-/t13-,15-,16-,17+,18-,20-,21+,25+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C25H37NO4 |
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Average Mass | 415.5740 Da |
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Monoisotopic Mass | 415.27226 Da |
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IUPAC Name | (3Z,5R)-3-{[(1S,2R,4aR,8S,8aR)-2-[(2S,3S)-2,3-dimethyloxiran-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-1-methyl-5-(propan-2-yl)pyrrolidine-2,4-dione |
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Traditional Name | (3Z,5R)-3-{[(1S,2R,4aR,8S,8aR)-2-[(2S,3S)-2,3-dimethyloxiran-2-yl]-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-isopropyl-1-methylpyrrolidine-2,4-dione |
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CAS Registry Number | Not Available |
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SMILES | CC(C)[C@H]1N(C)C(=O)\C(=C(/O)[C@H]2[C@@H]3[C@@H](C)CCC[C@H]3C=C(C)[C@@H]2[C@]2(C)O[C@H]2C)C1=O |
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InChI Identifier | InChI=1S/C25H37NO4/c1-12(2)21-23(28)19(24(29)26(21)7)22(27)18-17-13(3)9-8-10-16(17)11-14(4)20(18)25(6)15(5)30-25/h11-13,15-18,20-21,27H,8-10H2,1-7H3/b22-19-/t13-,15-,16-,17+,18-,20-,21+,25+/m0/s1 |
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InChI Key | PEBQSWUQULBCGF-SFOAYJPGSA-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 n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolidines |
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Sub Class | N-alkylpyrrolidines |
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Direct Parent | N-alkylpyrrolidines |
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Alternative Parents | |
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Substituents | - N-alkylpyrrolidine
- 3-pyrrolidone
- 2-pyrrolidone
- Pyrrolidone
- Vinylogous acid
- Tertiary carboxylic acid amide
- Cyclic ketone
- Lactam
- Ketone
- Carboxamide group
- Oxacycle
- Azacycle
- Ether
- Oxirane
- Enol
- Dialkyl ether
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Sharma S, Zaher S, Rodrigues PRS, Davies LC, Edkins S, Strang A, Chakraborty M, Watkins WJ, Andrews R, Parkinson E, Angelopoulos N, Moet L, Shepherd F, Davies KMM, White D, Oram S, Siddall K, Keeping V, Simpson K, Faggian F, Bray M, Bertorelli C, Bell S, Collis RE, McLaren JE, Labeta M, O'Donnell VB, Ghazal P: mSep: investigating physiological and immune-metabolic biomarkers in septic and healthy pregnant women to predict feto-maternal immune health - a prospective observational cohort study protocol. BMJ Open. 2022 Sep 17;12(9):e066382. doi: 10.1136/bmjopen-2022-066382. [PubMed:36115679 ]
- Fulton S, Janssen H, Salih S, James A, Elphinston RA: Feasibility and acceptability of a mobile model of environmental enrichment for patients with mixed medical conditions receiving inpatient rehabilitation: a mixed methods study. BMJ Open. 2022 Sep 17;12(9):e061212. doi: 10.1136/bmjopen-2022-061212. [PubMed:36115676 ]
- Vallejo-Yague E, Burkard T, Micheroli R, Burden AM: Minimal disease activity and remission in patients with psoriatic arthritis with elevated body mass index: an observational cohort study in the Swiss Clinical Quality Management cohort. BMJ Open. 2022 Sep 17;12(9):e061474. doi: 10.1136/bmjopen-2022-061474. [PubMed:36115672 ]
- Barker KL, Room J, Knight R, Hannink E, Newman M: Physiotherapy exercise rehabilitation with tailored exercise adherence support for people with osteoporosis and vertebral fractures: protocol for a randomised controlled trial - the OsteoPorosis Tailored exercise adherence INtervention (OPTIN) study. BMJ Open. 2022 Sep 17;12(9):e064637. doi: 10.1136/bmjopen-2022-064637. [PubMed:36115668 ]
- Wu Y, Ding L, Zheng C, Li H, Wu M, Sun Y, Liu X, Zhang X, Zeng Y: Targeted co-delivery of a photosensitizer and an antisense oligonucleotide based on an activatable hyaluronic acid nanosystem with endogenous oxygen generation for enhanced photodynamic therapy of hypoxic tumors. Acta Biomater. 2022 Sep 14. pii: S1742-7061(22)00588-8. doi: 10.1016/j.actbio.2022.09.025. [PubMed:36115655 ]
- LOTUS database [Link]
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