Record Information |
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Version | 1.0 |
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Created at | 2022-09-03 00:20:43 UTC |
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Updated at | 2022-09-03 00:20:43 UTC |
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NP-MRD ID | NP0165268 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (z)-2-[(2e,3r,4r,5s)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-{[(2s)-1-hydroxy-2-[(z,z)-3-methoxy-5-methylnaphthalene-1-carbonyloxy]-2-[(2s)-2-methyloxiran-2-yl]ethylidene]amino}-n-[(1z)-1-hydroxy-3-oxobut-1-en-2-yl]ethanimidic acid |
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Description | Azinomycin B belongs to the class of organic compounds known as naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. (z)-2-[(2e,3r,4r,5s)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-{[(2s)-1-hydroxy-2-[(z,z)-3-methoxy-5-methylnaphthalene-1-carbonyloxy]-2-[(2s)-2-methyloxiran-2-yl]ethylidene]amino}-n-[(1z)-1-hydroxy-3-oxobut-1-en-2-yl]ethanimidic acid is found in Streptomyces griseofuscus and Streptomyces sahachiroi. It was first documented in 2017 (PMID: 28513737). Based on a literature review a significant number of articles have been published on Azinomycin B (PMID: 35998388) (PMID: 35311535) (PMID: 32409837) (PMID: 31713613). |
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Structure | COC1=CC(C(=O)O[C@H](C(O)=N\C(\C(\O)=N\C(=C/O)\C(C)=O)=C2/[C@@H](OC(C)=O)[C@H](O)[C@@H]3CN23)[C@]2(C)CO2)=C2C=CC=C(C)C2=C1 InChI=1S/C31H33N3O11/c1-14-7-6-8-18-19(14)9-17(42-5)10-20(18)30(41)45-27(31(4)13-43-31)29(40)33-23(28(39)32-21(12-35)15(2)36)24-26(44-16(3)37)25(38)22-11-34(22)24/h6-10,12,22,25-27,35,38H,11,13H2,1-5H3,(H,32,39)(H,33,40)/b21-12-,24-23+/t22-,25+,26+,27+,31-,34?/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C31H33N3O11 |
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Average Mass | 623.6150 Da |
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Monoisotopic Mass | 623.21151 Da |
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IUPAC Name | (Z)-2-[(2E,3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-{[(2S)-1-hydroxy-2-[(Z,Z)-3-methoxy-5-methylnaphthalene-1-carbonyloxy]-2-[(2S)-2-methyloxiran-2-yl]ethylidene]amino}-N-[(1Z)-1-hydroxy-3-oxobut-1-en-2-yl]ethanimidic acid |
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Traditional Name | (Z)-2-[(2E,3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-{[(2S)-1-hydroxy-2-[(Z,Z)-3-methoxy-5-methylnaphthalene-1-carbonyloxy]-2-[(2S)-2-methyloxiran-2-yl]ethylidene]amino}-N-[(1Z)-1-hydroxy-3-oxobut-1-en-2-yl]ethanimidic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(C(=O)O[C@H](C(O)=N\C(\C(\O)=N\C(=C/O)\C(C)=O)=C2/[C@@H](OC(C)=O)[C@H](O)[C@@H]3CN23)[C@]2(C)CO2)=C2C=CC=C(C)C2=C1 |
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InChI Identifier | InChI=1S/C31H33N3O11/c1-14-7-6-8-18-19(14)9-17(42-5)10-20(18)30(41)45-27(31(4)13-43-31)29(40)33-23(28(39)32-21(12-35)15(2)36)24-26(44-16(3)37)25(38)22-11-34(22)24/h6-10,12,22,25-27,35,38H,11,13H2,1-5H3,(H,32,39)(H,33,40)/b21-12-,24-23+/t22-,25+,26+,27+,31-,34?/m0/s1 |
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InChI Key | QIKVYJOCQXXRSJ-PKDLRSQSSA-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 naphthalenecarboxylic acids and derivatives. Naphthalenecarboxylic acids and derivatives are compounds containing a naphthalene moiety, which bears a carboxylic acid group or a derivative at one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthalenecarboxylic acids and derivatives |
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Direct Parent | Naphthalenecarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - N-acyl-alpha amino acid or derivatives
- 1-naphthalenecarboxylic acid or derivatives
- Alpha-amino acid amide
- M-methoxybenzoic acid or derivatives
- Alpha-amino acid or derivatives
- Anisole
- Alkyl aryl ether
- Dicarboxylic acid or derivatives
- Fatty amide
- Fatty acyl
- Piperidine
- N-alkylpyrrolidine
- Alpha-branched alpha,beta-unsaturated-ketone
- Acryloyl-group
- Enone
- N-vinylaziridine
- Vinylaziridine
- Pyrrolidine
- Vinylogous amide
- Alpha,beta-unsaturated ketone
- Vinylogous acid
- Amino acid or derivatives
- Tertiary aliphatic amine
- Tertiary amine
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Ketone
- Carboxylic acid ester
- 1,2-aminoalcohol
- Organoheterocyclic compound
- Aziridine
- Azacycle
- Carboxylic acid derivative
- Oxacycle
- Dialkyl ether
- Enamine
- Ether
- Oxirane
- Amine
- Carbonyl group
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic oxide
- 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 | - Kurosawa S, Hasebe F, Okamura H, Yoshida A, Matsuda K, Sone Y, Tomita T, Shinada T, Takikawa H, Kuzuyama T, Kosono S, Nishiyama M: Molecular Basis for Enzymatic Aziridine Formation via Sulfate Elimination. J Am Chem Soc. 2022 Sep 7;144(35):16164-16170. doi: 10.1021/jacs.2c07243. Epub 2022 Aug 23. [PubMed:35998388 ]
- Bradley NP, Wahl KL, Steenwyk JL, Rokas A, Eichman BF: Resistance-Guided Mining of Bacterial Genotoxins Defines a Family of DNA Glycosylases. mBio. 2022 Apr 26;13(2):e0329721. doi: 10.1128/mbio.03297-21. Epub 2022 Mar 21. [PubMed:35311535 ]
- Bradley NP, Washburn LA, Christov PP, Watanabe CMH, Eichman BF: Escherichia coli YcaQ is a DNA glycosylase that unhooks DNA interstrand crosslinks. Nucleic Acids Res. 2020 Jul 27;48(13):7005-7017. doi: 10.1093/nar/gkaa346. [PubMed:32409837 ]
- Chen X, Sun Y, Wang S, Ying K, Xiao L, Liu K, Zuo X, He J: Identification of a novel structure-specific endonuclease AziN that contributes to the repair of azinomycin B-mediated DNA interstrand crosslinks. Nucleic Acids Res. 2020 Jan 24;48(2):709-718. doi: 10.1093/nar/gkz1067. [PubMed:31713613 ]
- Balazy M, Fausto A, Voskanian C, Chavez B, Panesar H, Minehan TG: Dimeric and trimeric derivatives of the azinomycin B chromophore show enhanced DNA binding. Org Biomol Chem. 2017 May 31;15(21):4522-4526. doi: 10.1039/c7ob00944e. [PubMed:28513737 ]
- LOTUS database [Link]
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