Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 22:29:59 UTC |
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Updated at | 2022-09-09 22:29:59 UTC |
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NP-MRD ID | NP0291417 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2e)-n-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-{3',5-dibromo-5'-[(2e)-2-{[2-(3-bromo-4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-2-(hydroxyimino)ethyl]-2',6-dihydroxy-[1,1'-biphenyl]-3-yl}-2-(n-hydroxyimino)propanimidic acid |
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Description | Bastadin 3 belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom. (2e)-n-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-{3',5-dibromo-5'-[(2e)-2-{[2-(3-bromo-4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}-2-(hydroxyimino)ethyl]-2',6-dihydroxy-[1,1'-biphenyl]-3-yl}-2-(n-hydroxyimino)propanimidic acid is found in Ianthella basta. It was first documented in 2004 (PMID: 15562403). Based on a literature review a small amount of articles have been published on Bastadin 3 (PMID: 23249297) (PMID: 17713818) (PMID: 20102170) (PMID: 22828961). |
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Structure | O\N=C(/CC1=CC(Br)=C(O)C(=C1)C1=CC(C\C(=N/O)C(O)=NCCC2=CC=C(O)C(Br)=C2)=CC(Br)=C1O)C(O)=NCCC1=CC=C(O)C(Br)=C1 InChI=1S/C34H30Br4N4O8/c35-23-11-17(1-3-29(23)43)5-7-39-33(47)27(41-49)15-19-9-21(31(45)25(37)13-19)22-10-20(14-26(38)32(22)46)16-28(42-50)34(48)40-8-6-18-2-4-30(44)24(36)12-18/h1-4,9-14,43-46,49-50H,5-8,15-16H2,(H,39,47)(H,40,48)/b41-27+,42-28+ |
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Synonyms | Not Available |
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Chemical Formula | C34H30Br4N4O8 |
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Average Mass | 942.2500 Da |
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Monoisotopic Mass | 937.87972 Da |
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IUPAC Name | (2E)-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-{3',5-dibromo-5'-[(2E)-2-{[2-(3-bromo-4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}-2-(hydroxyimino)ethyl]-2',6-dihydroxy-[1,1'-biphenyl]-3-yl}-2-(N-hydroxyimino)propanimidic acid |
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Traditional Name | (2E)-N-[2-(3-bromo-4-hydroxyphenyl)ethyl]-3-{3',5-dibromo-5'-[(2E)-2-{[2-(3-bromo-4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}-2-(hydroxyimino)ethyl]-2',6-dihydroxy-[1,1'-biphenyl]-3-yl}-2-(N-hydroxyimino)propanimidic acid |
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CAS Registry Number | Not Available |
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SMILES | O\N=C(/CC1=CC(Br)=C(O)C(=C1)C1=CC(C\C(=N/O)C(O)=NCCC2=CC=C(O)C(Br)=C2)=CC(Br)=C1O)C(O)=NCCC1=CC=C(O)C(Br)=C1 |
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InChI Identifier | InChI=1S/C34H30Br4N4O8/c35-23-11-17(1-3-29(23)43)5-7-39-33(47)27(41-49)15-19-9-21(31(45)25(37)13-19)22-10-20(14-26(38)32(22)46)16-28(42-50)34(48)40-8-6-18-2-4-30(44)24(36)12-18/h1-4,9-14,43-46,49-50H,5-8,15-16H2,(H,39,47)(H,40,48)/b41-27+,42-28+ |
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InChI Key | XEGSWNKCRGYRFG-CTQPMARESA-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 polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Biphenyls and derivatives |
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Direct Parent | Polybrominated biphenyls |
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Alternative Parents | |
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Substituents | - Polybrominated biphenyl
- 2-halophenol
- 2-bromophenol
- 1-hydroxy-2-unsubstituted benzenoid
- Bromobenzene
- Phenol
- Halobenzene
- Aryl bromide
- Aryl halide
- Fatty acyl
- Fatty amide
- Ketoxime
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Oxime
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organobromide
- Organohalogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | - Niemann H, Lin W, Muller WE, Kubbutat M, Lai D, Proksch P: Trimeric hemibastadin congener from the marine sponge Ianthella basta. J Nat Prod. 2013 Jan 25;76(1):121-5. doi: 10.1021/np300764u. Epub 2012 Dec 18. [PubMed:23249297 ]
- Ortlepp S, Sjogren M, Dahlstrom M, Weber H, Ebel R, Edrada R, Thoms C, Schupp P, Bohlin L, Proksch P: Antifouling activity of bromotyrosine-derived sponge metabolites and synthetic analogues. Mar Biotechnol (NY). 2007 Nov-Dec;9(6):776-85. doi: 10.1007/s10126-007-9029-x. Epub 2007 Aug 23. [PubMed:17713818 ]
- Calcul L, Inman WD, Morris AA, Tenney K, Ratnam J, McKerrow JH, Valeriote FA, Crews P: Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations. J Nat Prod. 2010 Mar 26;73(3):365-72. doi: 10.1021/np9005986. [PubMed:20102170 ]
- Perez-Rodriguez S, Pereira-Cameselle R, de Lera AR: First total synthesis of dioxepine bastadin 3. Org Biomol Chem. 2012 Sep 14;10(34):6945-50. doi: 10.1039/c2ob25874a. Epub 2012 Jul 24. [PubMed:22828961 ]
- Couladouros EA, Pitsinos EN, Moutsos VI, Sarakinos G: A general method for the synthesis of bastaranes and isobastaranes: first total synthesis of bastadins 5, 10, 12, 16, 20, and 21. Chemistry. 2004 Dec 17;11(1):406-21. doi: 10.1002/chem.200400904. [PubMed:15562403 ]
- LOTUS database [Link]
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