| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-20 23:57:18 UTC |
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| Updated at | 2025-02-11 15:45:51 UTC |
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| NP-MRD ID | NP0042246 |
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| Natural Product DOI | https://doi.org/10.57994/0595 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (+)-versicolamide B |
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| Provided By | JEOL Database |
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| Description | (+)-Versicolamide B belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. (+)-versicolamide B is found in Aspergillus taichungensis. (+)-versicolamide B was first documented in 2015 (PMID: 25615822). Based on a literature review a small amount of articles have been published on (+)-Versicolamide B (PMID: 32672903) (PMID: 37097072). |
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| Structure | [H]N1C(=O)[C@@]2(C3=C1C1=C(OC(C([H])=C1[H])(C([H])([H])[H])C([H])([H])[H])C([H])=C3[H])C([H])([H])[C@@]13N([H])C(=O)[C@@]4(N(C1=O)C([H])([H])C([H])([H])C4([H])[H])C([H])([H])[C@]3([H])C2(C([H])([H])[H])C([H])([H])[H] InChI=1S/C26H29N3O4/c1-22(2)10-8-14-16(33-22)7-6-15-18(14)27-20(31)25(15)13-26-17(23(25,3)4)12-24(19(30)28-26)9-5-11-29(24)21(26)32/h6-8,10,17H,5,9,11-13H2,1-4H3,(H,27,31)(H,28,30)/t17-,24+,25+,26+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C26H29N3O4 |
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| Average Mass | 447.5350 Da |
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| Monoisotopic Mass | 447.21581 Da |
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| IUPAC Name | (1'S,3S,3'R,7'S)-4',4',7,7-tetramethyl-2,7-dihydro-1H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,8',13'-trione |
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| Traditional Name | (1'S,3S,3'R,7'S)-4',4',7,7-tetramethyl-1H-9',14'-diazaspiro[chromeno[5,6-b]pyrrole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,8',13'-trione |
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| CAS Registry Number | Not Available |
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| SMILES | [H]N1C(=O)[C@@]2(C3=C1C1=C(OC(C([H])=C1[H])(C([H])([H])[H])C([H])([H])[H])C([H])=C3[H])C([H])([H])[C@@]13N([H])C(=O)[C@@]4(N(C1=O)C([H])([H])C([H])([H])C4([H])[H])C([H])([H])[C@]3([H])C2(C([H])([H])[H])C([H])([H])[H] |
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| InChI Identifier | InChI=1S/C26H29N3O4/c1-22(2)10-8-14-16(33-22)7-6-15-18(14)27-20(31)25(15)13-26-17(23(25,3)4)12-24(19(30)28-26)9-5-11-29(24)21(26)32/h6-8,10,17H,5,9,11-13H2,1-4H3,(H,27,31)(H,28,30)/t17-,24+,25+,26+/m1/s1 |
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| InChI Key | RNWRZMCJFWSZOX-XRNKBYASSA-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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| 1D NMR | 13C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | 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, 400, C3D6O, simulated) | zhangcuixian@gzucm.edu.cn | guangzhou university of Chinese medicine | zhangcuixian | 2024-05-11 | View Spectrum |
| | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Aspergillus taichungensis | JEOL database | - Cai, S., et al, Org. Lett. 15, 2168 (2013)
| | Aspergillus versicolor CGF 9-1-2 | | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Benzopyrans |
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| Sub Class | 1-benzopyrans |
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| Direct Parent | 2,2-dimethyl-1-benzopyrans |
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| Alternative Parents | |
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| Substituents | - 2,2-dimethyl-1-benzopyran
- Alpha-amino acid or derivatives
- Azaspirodecane
- Indole or derivatives
- Dihydroindole
- Indolizidine
- Dioxopiperazine
- 2,5-dioxopiperazine
- Alkyl aryl ether
- Delta-lactam
- N-alkylpiperazine
- Piperidinone
- 1,4-diazinane
- Benzenoid
- Piperazine
- Piperidine
- Pyrrolidine
- Tertiary carboxylic acid amide
- Secondary carboxylic acid amide
- Lactam
- Carboxamide group
- Azacycle
- Ether
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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 | - Gao S, Tian WJ, Liao ZJ, Wang GH, Zeng DQ, Liu XZ, Wang XY, Zhou H, Chen HF, Lin T: Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii. Chem Biodivers. 2020 Sep;17(9):e2000424. doi: 10.1002/cbdv.202000424. Epub 2020 Aug 31. [PubMed:32672903 ]
- Kato H, Nakahara T, Sugimoto K, Matsuo K, Kagiyama I, Frisvad JC, Sherman DH, Williams RM, Tsukamoto S: Isolation of notoamide S and enantiomeric 6-epi-stephacidin A from the fungus Aspergillus amoenus: biogenetic implications. Org Lett. 2015 Feb 6;17(3):700-3. doi: 10.1021/ol5037198. Epub 2015 Jan 23. [PubMed:25615822 ]
- Hu JS, He YP, Zhou FG, Wu PP, Chen LY, Ni C, Zhang ZK, Xiao XJ, An LK, He XX, Zhang CX: New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2. Chem Biodivers. 2023 Jun;20(6):e202300301. doi: 10.1002/cbdv.202300301. Epub 2023 May 17. [PubMed:37097072 ]
- Cai, S., et al. (2013). Cai, S., et al, Org. Lett. 15, 2168 (2013). Org. Lett..
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