Record Information |
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Version | 1.0 |
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Created at | 2020-09-23 01:57:34 UTC |
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Updated at | 2021-08-10 02:55:27 UTC |
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NP-MRD ID | NP0001586 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tumonic acid B |
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Provided By | NPAtlas |
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Description | (2S)-2-{[(2R,3S)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoyl]oxy}propanoic acid belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating. Tumonic acid B is found in Lyngbya majuscula. It was first documented in 1999 (PMID: 10096859). Based on a literature review very few articles have been published on (2S)-2-{[(2R,3S)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoyl]oxy}propanoic acid (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189). |
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Structure | [H]OC(=O)[C@@]([H])(OC(=O)[C@]([H])(OC(=O)[C@@]1([H])N(C(=O)[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H] InChI=1S/C28H47NO8/c1-7-9-10-11-12-13-15-19(4)23(30)20(5)25(31)29-17-14-16-22(29)27(34)37-24(18(3)8-2)28(35)36-21(6)26(32)33/h15,18,20-24,30H,7-14,16-17H2,1-6H3,(H,32,33)/b19-15+/t18-,20+,21-,22-,23-,24+/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-{[(2R,3S)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoyl]oxy}propanoate | Generator | Tumonate b | Generator |
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Chemical Formula | C28H47NO8 |
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Average Mass | 525.6830 Da |
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Monoisotopic Mass | 525.33017 Da |
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IUPAC Name | (2S)-2-{[(2R,3S)-2-[(2S)-1-[(2R,3R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoyl]oxy}propanoic acid |
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Traditional Name | (2S)-2-{[(2R,3S)-2-[(2S)-1-[(2R,3R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoyl]oxy}propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)[C@@]([H])(OC(=O)[C@]([H])(OC(=O)[C@@]1([H])N(C(=O)[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C28H47NO8/c1-7-9-10-11-12-13-15-19(4)23(30)20(5)25(31)29-17-14-16-22(29)27(34)37-24(18(3)8-2)28(35)36-21(6)26(32)33/h15,18,20-24,30H,7-14,16-17H2,1-6H3,(H,32,33)/b19-15+/t18-,20+,21-,22-,23-,24+/m0/s1 |
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InChI Key | HYPDCGGBAFGHKA-WRZMLGOZSA-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 | Belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Peptidomimetics |
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Sub Class | Depsipeptides |
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Direct Parent | Depsipeptides |
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Alternative Parents | |
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Substituents | - Depsipeptide
- Alpha-amino acid ester
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Proline or derivatives
- Alpha-amino acid or derivatives
- Tricarboxylic acid or derivatives
- N-acylpyrrolidine
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Fatty acid ester
- Monosaccharide
- Fatty acyl
- Tertiary carboxylic acid amide
- Pyrrolidine
- Secondary alcohol
- Carboxylic acid ester
- Carboxamide group
- Carboxylic acid derivative
- Carboxylic acid
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organopnictogen compound
- Carbonyl group
- Organic nitrogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | - Harrigan GG, Luesch H, Yoshida WY, Moore RE, Nagle DG, Biggs J, Park PU, Paul VJ: Tumonoic acids, novel metabolites from a cyanobacterial assemblage of Lyngbya majuscula and Schizothrix calcicola. J Nat Prod. 1999 Mar;62(3):464-7. doi: 10.1021/np980460u. [PubMed:10096859 ]
- Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
- Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
- Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
- Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]
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