| Record Information |
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| Version | 2.0 |
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| Created at | 2024-06-10 22:51:00 UTC |
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| Updated at | 2025-02-11 15:48:18 UTC |
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| NP-MRD ID | NP0333404 |
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| Natural Product DOI | https://doi.org/10.57994/2801 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Brevianamide-E2 |
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| Description | Brevianamide-E2 belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on Brevianamide-E2. |
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| Structure | CC(C)(C=C)[C@@]12NC3=CC=CC=C3[C@]1(O)C[C@@]1(NC(=O)[C@@H]3CCCN3C1=O)O2 InChI=1S/C21H25N3O4/c1-4-18(2,3)21-19(27,13-8-5-6-9-14(13)22-21)12-20(28-21)17(26)24-11-7-10-15(24)16(25)23-20/h4-6,8-9,15,22,27H,1,7,10-12H2,2-3H3,(H,23,25)/t15-,19+,20+,21-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C21H25N3O4 |
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| Average Mass | 383.4480 Da |
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| Monoisotopic Mass | 383.18451 Da |
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| IUPAC Name | (2R,3aR,8aS,8'aS)-3a-hydroxy-8a-(2-methylbut-3-en-2-yl)-2',3,3a,4',6',7',8,8',8a,8'a-decahydro-1'H-spiro[furo[2,3-b]indole-2,3'-pyrrolo[1,2-a]pyrazine]-1',4'-dione |
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| Traditional Name | (2R,3aR,8aS,8'aS)-3a-hydroxy-8a-(2-methylbut-3-en-2-yl)-3,6',7',8,8',8'a-hexahydro-2'H-spiro[furo[2,3-b]indole-2,3'-pyrrolo[1,2-a]pyrazine]-1',4'-dione |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)(C=C)[C@@]12NC3=CC=CC=C3[C@]1(O)C[C@@]1(NC(=O)[C@@H]3CCCN3C1=O)O2 |
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| InChI Identifier | InChI=1S/C21H25N3O4/c1-4-18(2,3)21-19(27,13-8-5-6-9-14(13)22-21)12-20(28-21)17(26)24-11-7-10-15(24)16(25)23-20/h4-6,8-9,15,22,27H,1,7,10-12H2,2-3H3,(H,23,25)/t15-,19+,20+,21-/m0/s1 |
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| InChI Key | QGGDYDAZASEHIB-NOOVBMIQSA-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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| COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C3D6O, experimental) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | 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, 600.314502325, C2D6OS, simulated) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600.314502325, C3D6O, simulated) | quan.khong@nih.gov | National Cancer Institute at Frederick | Quan T. Khong | 2024-06-10 | View Spectrum |
| | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Moorena sp. | | |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | N-acyl-alpha amino acids and derivatives |
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| Alternative Parents | |
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| Substituents | - N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Dihydroindole
- Indole or derivatives
- 2,5-dioxopiperazine
- Pyrrolidine-2-carboxamide
- Pyrrolidine carboxylic acid or derivatives
- N-acylpyrrolidine
- Dioxopiperazine
- N-alkylpiperazine
- Secondary aliphatic/aromatic amine
- Fatty acyl
- Benzenoid
- Piperazine
- N-acyl-amine
- Monosaccharide
- Fatty amide
- 1,4-diazinane
- Tetrahydrofuran
- Tertiary carboxylic acid amide
- Tertiary alcohol
- Pyrrolidine
- Lactam
- Carboxamide group
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- 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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