| Record Information |
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| Version | 2.0 |
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| Created at | 2023-12-01 20:01:23 UTC |
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| Updated at | 2024-09-03 04:18:19 UTC |
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| NP-MRD ID | NP0332185 |
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| Natural Product DOI | https://doi.org/10.57994/1354 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Caulamidine B |
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| Description | Caulamidine B belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. Caulamidine B was first documented in 2018 (PMID: 29619201). Based on a literature review very few articles have been published on Caulamidine B (PMID: 37368408). |
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| Structure | CN1CC[C@@]23CC4=C(C=C(Br)C=C4)N=C2N(C)C[C@@H](Cl)[C@]32C1=NC1=C2C=CC(Br)=C1 InChI=1S/C23H21Br2ClN4/c1-29-8-7-22-11-13-3-4-14(24)9-17(13)27-20(22)30(2)12-19(26)23(22)16-6-5-15(25)10-18(16)28-21(23)29/h3-6,9-10,19H,7-8,11-12H2,1-2H3/t19-,22-,23-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C23H21Br2ClN4 |
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| Average Mass | 548.7100 Da |
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| Monoisotopic Mass | 545.98215 Da |
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| IUPAC Name | (1R,13S,14S)-6,18-dibromo-13-chloro-11,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,9,15(20),16,18,21-octaene |
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| Traditional Name | (1R,13S,14S)-6,18-dibromo-13-chloro-11,23-dimethyl-9,11,21,23-tetraazahexacyclo[12.11.0.0^{1,10}.0^{3,8}.0^{14,22}.0^{15,20}]pentacosa-3(8),4,6,9,15(20),16,18,21-octaene |
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| CAS Registry Number | Not Available |
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| SMILES | CN1CC[C@@]23CC4=C(C=C(Br)C=C4)N=C2N(C)C[C@@H](Cl)[C@]32C1=NC1=C2C=CC(Br)=C1 |
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| InChI Identifier | InChI=1S/C23H21Br2ClN4/c1-29-8-7-22-11-13-3-4-14(24)9-17(13)27-20(22)30(2)12-19(26)23(22)16-6-5-15(25)10-18(16)28-21(23)29/h3-6,9-10,19H,7-8,11-12H2,1-2H3/t19-,22-,23-/m1/s1 |
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| InChI Key | FKYDRUSZQJYVQJ-UEVCKROQSA-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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| NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HMBC NMR | [1H, 15N] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HMBC NMR | [1H, 15N] NMR Spectrum (2D, 600 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3CN, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | dongdong.wang@nih.gov | NCI-Frederick | Dong Wang | 2024-05-09 | 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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| Not Available | | 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 aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Quinolines and derivatives |
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| Sub Class | Aminoquinolines and derivatives |
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| Direct Parent | Aminoquinolines and derivatives |
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| Alternative Parents | |
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| Substituents | - Aminoquinoline
- Diazanaphthalene
- 3-alkylindole
- Naphthyridine
- Azaspirodecane
- Indole or derivatives
- Imidolactam
- Benzenoid
- Piperidine
- Azacycle
- Bromoalkene
- Haloalkene
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Vinyl halide
- Vinyl bromide
- Amidine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Organochloride
- Organobromide
- Organohalogen compound
- Alkyl halide
- Alkyl chloride
- 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 | - Tian X, Wang D, Jiang W, Bokesch HR, Wilson BAP, O'Keefe BR, Gustafson KR: Rare Caulamidine Hexacyclic Alkaloids from the Marine Ascidian Polyandrocarpa sp. J Nat Prod. 2023 Jul 28;86(7):1855-1861. doi: 10.1021/acs.jnatprod.3c00393. Epub 2023 Jun 27. [PubMed:37368408 ]
- Milanowski DJ, Oku N, Cartner LK, Bokesch HR, Williamson RT, Sauri J, Liu Y, Blinov KA, Ding Y, Li XC, Ferreira D, Walker LA, Khan S, Davies-Coleman MT, Kelley JA, McMahon JB, Martin GE, Gustafson KR: Unequivocal determination of caulamidines A and B: application and validation of new tools in the structure elucidation tool box. Chem Sci. 2017 Nov 6;9(2):307-314. doi: 10.1039/c7sc01996c. eCollection 2018 Jan 14. [PubMed:29619201 ]
- DOI: 10.1021/acs.jnatprod.3c00393
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