| Record Information |
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| Version | 2.0 |
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| Created at | 2020-12-09 00:53:24 UTC |
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| Updated at | 2021-07-15 16:47:11 UTC |
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| NP-MRD ID | NP0003717 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Mumbaistatin |
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| Provided By | NPAtlas |
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| Description | Mumbaistatin is found in Streptomyces. Mumbaistatin was first documented in 2001 (PMID: 11426660). Based on a literature review very few articles have been published on 1-[2-(5-carboxy-4-hydroxypentanoyl)-6-hydroxybenzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (PMID: 21274958) (PMID: 20486934) (PMID: 19074414) (PMID: 17524653). |
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| Structure | [H]OC(=O)C1=C(C(=O)C2=C(O[H])C([H])=C([H])C([H])=C2C(=O)C([H])([H])C([H])([H])[C@@]([H])(O[H])C([H])([H])C(=O)O[H])C2=C(C([H])=C1O[H])C(=O)C1=C([H])C([H])=C([H])C(O[H])=C1C2=O InChI=1S/C28H20O12/c29-11(9-19(34)35)7-8-15(30)12-3-1-5-16(31)20(12)27(38)24-22-14(10-18(33)23(24)28(39)40)25(36)13-4-2-6-17(32)21(13)26(22)37/h1-6,10-11,29,31-33H,7-9H2,(H,34,35)(H,39,40)/t11-/m1/s1 |
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| Synonyms | | Value | Source |
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| 1-[2-(5-Carboxy-4-hydroxypentanoyl)-6-hydroxybenzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate | Generator |
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| Chemical Formula | C28H20O12 |
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| Average Mass | 548.4560 Da |
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| Monoisotopic Mass | 548.09548 Da |
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| IUPAC Name | 1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid |
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| Traditional Name | 1-{2-[(4R)-5-carboxy-4-hydroxypentanoyl]-6-hydroxybenzoyl}-3,8-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid |
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| CAS Registry Number | Not Available |
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| SMILES | OC(CCC(=O)C1=C(C(=O)C2=C3C(=O)C4=C(C=CC=C4O)C(=O)C3=CC(O)=C2C(O)=O)C(O)=CC=C1)CC(O)=O |
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| InChI Identifier | InChI=1S/C28H20O12/c29-11(9-19(34)35)7-8-15(30)12-3-1-5-16(31)20(12)27(38)24-22-14(10-18(33)23(24)28(39)40)25(36)13-4-2-6-17(32)21(13)26(22)37/h1-6,10-11,29,31-33H,7-9H2,(H,34,35)(H,39,40) |
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| InChI Key | XFESZXMDORIFAO-UHFFFAOYSA-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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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Anthracenes |
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| Sub Class | Anthracenecarboxylic acids and derivatives |
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| Direct Parent | Anthracenecarboxylic acids |
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| Alternative Parents | |
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| Substituents | - Anthracene carboxylic acid
- 9,10-anthraquinone
- Anthraquinone
- Hydroxyanthraquinone
- Benzophenone
- Alkyl-phenylketone
- Aryl-phenylketone
- 2-naphthalenecarboxylic acid
- 1-naphthalenecarboxylic acid or derivatives
- 2-naphthalenecarboxylic acid or derivatives
- Butyrophenone
- Hydroxybenzoic acid
- Salicylic acid or derivatives
- Phenylketone
- Medium-chain keto acid
- Aryl ketone
- Aryl alkyl ketone
- Benzoyl
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Beta-hydroxy acid
- Monocyclic benzene moiety
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Vinylogous acid
- Secondary alcohol
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic 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 | - Vertesy L, Kurz M, Paulus EF, Schummer D, Hammann P: The chemical structure of mumbaistatin, a novel glucose-6-phosphate translocase inhibitor produced by Streptomyces sp. DSM 11641. J Antibiot (Tokyo). 2001 Apr;54(4):354-63. doi: 10.7164/antibiotics.54.354. [PubMed:11426660 ]
- Neufeind S, Hulsken N, Neudorfl JM, Schlorer N, Schmalz HG: Total synthesis of cyclo-mumbaistatin analogues through anionic homo-Fries rearrangement. Chemistry. 2011 Feb 25;17(9):2633-41. doi: 10.1002/chem.201003166. Epub 2011 Jan 27. [PubMed:21274958 ]
- Tahanian E, Lord-Dufour S, Das A, Khosla C, Roy R, Annabi B: Inhibition of tubulogenesis and of carcinogen-mediated signaling in brain endothelial cells highlight the antiangiogenic properties of a mumbaistatin analog. Chem Biol Drug Des. 2010 May;75(5):481-8. doi: 10.1111/j.1747-0285.2010.00961.x. [PubMed:20486934 ]
- Lord-Dufour S, Copland IB, Levros LC Jr, Post M, Das A, Khosla C, Galipeau J, Rassart E, Annabi B: Evidence for transcriptional regulation of the glucose-6-phosphate transporter by HIF-1alpha: Targeting G6PT with mumbaistatin analogs in hypoxic mesenchymal stromal cells. Stem Cells. 2009 Mar;27(3):489-97. doi: 10.1634/stemcells.2008-0855. [PubMed:19074414 ]
- Lee TS, Das A, Khosla C: Structure-activity relationships of semisynthetic mumbaistatin analogs. Bioorg Med Chem. 2007 Aug 1;15(15):5207-18. doi: 10.1016/j.bmc.2007.05.019. Epub 2007 May 23. [PubMed:17524653 ]
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