Record Information |
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Version | 2.0 |
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Created at | 2020-12-09 02:29:56 UTC |
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Updated at | 2021-07-15 16:51:15 UTC |
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NP-MRD ID | NP0005174 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | BE-14106 |
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Provided By | NPAtlas |
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Description | BE-14106 is also known as GT32-a. BE-14106 is found in Streptomyces and Streptomyces spheroides A14106 (FERM-P11378). BE-14106 was first documented in 1992 (PMID: 1500352). Based on a literature review a small amount of articles have been published on BE-14106 (PMID: 19854930) (PMID: 27331864) (PMID: 24407644) (PMID: 19875084). |
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Structure | [H]O[C@]1([H])\C([H])=C(\[H])/C(/[H])=C(/[H])\C(=C(\[H])/C(/[H])=C([H])\C([H])([H])[C@]([H])(N([H])C(=O)\C([H])=C(\[H])/C(/[H])=C(/[H])\C(=C([H])/[C@@]1([H])O[H])\C([H])([H])[H])C([H])([H])C(\[H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H] InChI=1S/C27H37NO3/c1-4-5-6-7-17-24-18-11-8-14-22(2)15-9-12-19-25(29)26(30)21-23(3)16-10-13-20-27(31)28-24/h6-16,19-21,24-26,29-30H,4-5,17-18H2,1-3H3,(H,28,31)/b7-6+,11-8-,15-9-,16-10-,19-12-,20-13-,22-14-,23-21-/t24-,25-,26-/m1/s1 |
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Synonyms | |
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Chemical Formula | C27H37NO3 |
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Average Mass | 423.5970 Da |
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Monoisotopic Mass | 423.27734 Da |
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IUPAC Name | (3Z,5Z,7Z,9R,10R,11Z,13Z,15Z,17Z,20R)-20-[(2E)-hex-2-en-1-yl]-9,10-dihydroxy-7,15-dimethyl-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one |
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Traditional Name | (3Z,5Z,7Z,9R,10R,11Z,13Z,15Z,17Z,20R)-20-[(2E)-hex-2-en-1-yl]-9,10-dihydroxy-7,15-dimethyl-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCC\C=C\CC1C\C=C/C=C(/C)\C=C/C=C\C(O)C(O)\C=C(\C)/C=C\C=C/C(=O)N1 |
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InChI Identifier | InChI=1S/C27H37NO3/c1-4-5-6-7-17-24-18-11-8-14-22(2)15-9-12-19-25(29)26(30)21-23(3)16-10-13-20-27(31)28-24/h6-16,19-21,24-26,29-30H,4-5,17-18H2,1-3H3,(H,28,31)/b7-6+,11-8-,15-9-,16-10-,19-12-,20-13-,22-14-,23-21- |
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InChI Key | ALYLZDHKQZUVDF-SFDMNNJASA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 | Species Name | Source | Reference |
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Streptomyces | NPAtlas | | Streptomyces spheroides A14106 (FERM-P11378) | Bacteria | |
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Chemical Taxonomy |
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Classification | Not classified |
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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 | - Kojiri K, Nakajima S, Suzuki H, Kondo H, Suda H: A new macrocyclic lactam antibiotic, BE-14106. I. Taxonomy, isolation, biological activity and structural elucidation. J Antibiot (Tokyo). 1992 Jun;45(6):868-74. doi: 10.7164/antibiotics.45.868. [PubMed:1500352 ]
- Jorgensen H, Degnes KF, Dikiy A, Fjaervik E, Klinkenberg G, Zotchev SB: Insights into the evolution of macrolactam biosynthesis through cloning and comparative analysis of the biosynthetic gene cluster for a novel macrocyclic lactam, ML-449. Appl Environ Microbiol. 2010 Jan;76(1):283-93. doi: 10.1128/AEM.00744-09. Epub 2009 Oct 23. [PubMed:19854930 ]
- Fujita K, Sugiyama R, Nishimura S, Ishikawa N, Arai MA, Ishibashi M, Kakeya H: Stereochemical Assignment and Biological Evaluation of BE-14106 Unveils the Importance of One Acetate Unit for the Antifungal Activity of Polyene Macrolactams. J Nat Prod. 2016 Jul 22;79(7):1877-80. doi: 10.1021/acs.jnatprod.6b00250. Epub 2016 Jun 22. [PubMed:27331864 ]
- Flinspach K, Ruckert C, Kalinowski J, Heide L, Apel AK: Draft Genome Sequence of Streptomyces niveus NCIMB 11891, Producer of the Aminocoumarin Antibiotic Novobiocin. Genome Announc. 2014 Jan 9;2(1). pii: 2/1/e01146-13. doi: 10.1128/genomeA.01146-13. [PubMed:24407644 ]
- Jorgensen H, Degnes KF, Sletta H, Fjaervik E, Dikiy A, Herfindal L, Bruheim P, Klinkenberg G, Bredholt H, Nygard G, Doskeland SO, Ellingsen TE, Zotchev SB: Biosynthesis of macrolactam BE-14106 involves two distinct PKS systems and amino acid processing enzymes for generation of the aminoacyl starter unit. Chem Biol. 2009 Oct 30;16(10):1109-21. doi: 10.1016/j.chembiol.2009.09.014. [PubMed:19875084 ]
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