Record Information |
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Version | 1.0 |
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Created at | 2021-01-05 23:47:59 UTC |
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Updated at | 2021-07-15 17:17:58 UTC |
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NP-MRD ID | NP0014696 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tetrangomycin |
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Provided By | NPAtlas![NPAtlas Logo](/attributions/npatlas_logo_square_small.png) |
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Description | Tetrangomycin is found in Apis cerana, Streptomyces cyanogenus, Streptomyces globisporus, Streptomyces globosus, Streptomyces sp. CB01913 and Streptomyces ederensis. It was first documented in 1965 (PMID: 5883506). Based on a literature review a small amount of articles have been published on Tetrangomycin (PMID: 26335269) (PMID: 5919937) (PMID: 11671566) (PMID: 8990300). |
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Structure | [H]OC1=C2C(=O)C3=C(C(=O)C2=C([H])C([H])=C1[H])C1=C(C([H])=C3[H])C([H])([H])[C@](O[H])(C([H])([H])[H])C([H])([H])C1=O InChI=1S/C19H14O5/c1-19(24)7-9-5-6-11-16(14(9)13(21)8-19)18(23)10-3-2-4-12(20)15(10)17(11)22/h2-6,20,24H,7-8H2,1H3/t19-/m1/s1 |
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Synonyms | Value | Source |
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(-)-Tetrangomycin | ChEBI | (+)-3,4-Dihydro-3,8-dihydroxy-3-methylbenz(a)anthracene- 1,7,12(2H)-trione | ChEBI |
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Chemical Formula | C19H14O5 |
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Average Mass | 322.3160 Da |
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Monoisotopic Mass | 322.08412 Da |
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IUPAC Name | (3R)-3,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione |
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Traditional Name | (3R)-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione |
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CAS Registry Number | Not Available |
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SMILES | C[C@]1(O)CC(=O)C2=C(C1)C=CC1=C2C(=O)C2=C(C(O)=CC=C2)C1=O |
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InChI Identifier | InChI=1S/C19H14O5/c1-19(24)7-9-5-6-11-16(14(9)13(21)8-19)18(23)10-3-2-4-12(20)15(10)17(11)22/h2-6,20,24H,7-8H2,1H3/t19-/m1/s1 |
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InChI Key | UGEKKXLEYACFTD-LJQANCHMSA-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 | |
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Species Where Detected | |
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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 | - Ma M, Rateb ME, Teng Q, Yang D, Rudolf JD, Zhu X, Huang Y, Zhao LX, Jiang Y, Li X, Rader C, Duan Y, Shen B: Angucyclines and Angucyclinones from Streptomyces sp. CB01913 Featuring C-Ring Cleavage and Expansion. J Nat Prod. 2015 Oct 23;78(10):2471-80. doi: 10.1021/acs.jnatprod.5b00601. Epub 2015 Sep 3. [PubMed:26335269 ]
- Kuntsmann MP, Mitscher LA: The structural characterization of tetrangomycin and tetrangulol. J Org Chem. 1966 Sep;31(9):2920-5. doi: 10.1021/jo01347a043. [PubMed:5919937 ]
- Krohn K, Boker N, Florke U, Freund C: Synthesis of Angucyclines. 8. Biomimetic-Type Synthesis of Rabelomycin, Tetrangomycin, and Related Ring B Aromatic Angucyclinones. J Org Chem. 1997 Apr 18;62(8):2350-2356. doi: 10.1021/jo9622587. [PubMed:11671566 ]
- Dann M, Lefemine DV, Barbatschi F, Shu P, Kunstmann MP, Mitscher LA, Bohonos N: Tetrangomycin, a new quinone antibiotic. Antimicrob Agents Chemother (Bethesda). 1965;5:832-5. [PubMed:5883506 ]
- Hong ST, Carney JR, Gould SJ: Cloning and heterologous expression of the entire gene clusters for PD 116740 from Streptomyces strain WP 4669 and tetrangulol and tetrangomycin from Streptomyces rimosus NRRL 3016. J Bacteriol. 1997 Jan;179(2):470-6. doi: 10.1128/jb.179.2.470-476.1997. [PubMed:8990300 ]
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