Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 17:03:18 UTC |
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Updated at | 2022-09-11 17:03:18 UTC |
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NP-MRD ID | NP0317271 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,2s)-2-[(2r,4z,6e,8s,9r,13r,15r,16r)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid |
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Description | Borrelidin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1s,2s)-2-[(2r,4z,6e,8s,9r,13r,15r,16r)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid is found in Streptomyces albovinaceus. It was first documented in 2020 (PMID: 32253314). Based on a literature review a significant number of articles have been published on Borrelidin (PMID: 35063731) (PMID: 34804423) (PMID: 33681712) (PMID: 32250597). |
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Structure | C[C@@H]1CC(C)C[C@@H](C)[C@H](O)\C(=C\C=C/C[C@@H](OC(=O)C[C@@H](O)[C@H](C)C1)[C@H]1CCC[C@@H]1C(O)=O)C#N InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5-,21-8+/t17-,18?,19-,20-,22+,23+,24-,25-,27+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C28H43NO6 |
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Average Mass | 489.6530 Da |
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Monoisotopic Mass | 489.30904 Da |
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IUPAC Name | (1S,2S)-2-[(2R,4Z,6E,8S,9R,13R,15R,16R)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid |
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Traditional Name | (1S,2S)-2-[(2R,4Z,6E,8S,9R,13R,15R,16R)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC(C)C[C@@H](C)[C@H](O)\C(=C\C=C/C[C@@H](OC(=O)C[C@@H](O)[C@H](C)C1)[C@H]1CCC[C@@H]1C(O)=O)C#N |
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InChI Identifier | InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5-,21-8+/t17-,18?,19-,20-,22+,23+,24-,25-,27+/m1/s1 |
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InChI Key | OJCKRNPLOZHAOU-MJQQLCDASA-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 macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolides and analogues |
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Sub Class | Not Available |
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Direct Parent | Macrolides and analogues |
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Alternative Parents | |
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Substituents | - Macrolide
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Nitrile
- Carbonitrile
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- 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 | - Li K, Chen S, Pang X, Cai J, Zhang X, Liu Y, Zhu Y, Zhou X: Natural products from mangrove sediments-derived microbes: Structural diversity, bioactivities, biosynthesis, and total synthesis. Eur J Med Chem. 2022 Feb 15;230:114117. doi: 10.1016/j.ejmech.2022.114117. Epub 2022 Jan 12. [PubMed:35063731 ]
- Rakhmawatie MD, Wibawa T, Lisdiyanti P, Pratiwi WR, Damayanti E, Mustofa: Potential secondary metabolite from Indonesian Actinobacteria (InaCC A758) against Mycobacterium tuberculosis. Iran J Basic Med Sci. 2021 Aug;24(8):1058-1068. doi: 10.22038/ijbms.2021.56468.12601. [PubMed:34804423 ]
- Shin J, Yang SH, Du YE, Park K, Kim D, Shin D, Kim J, Kim SH, Kim YK, Shin J, Oh DC, Kim Y: Borrelidin from Saltern-Derived Halophilic Nocardiopsis sp. Dissociates Amyloid-beta and Tau Fibrils. J Alzheimers Dis Rep. 2021 Jan 11;5(1):7-13. doi: 10.3233/ADR-200247. [PubMed:33681712 ]
- Kim Y, Sundrud MS, Zhou C, Edenius M, Zocco D, Powers K, Zhang M, Mazitschek R, Rao A, Yeo CY, Noss EH, Brenner MB, Whitman M, Keller TL: Aminoacyl-tRNA synthetase inhibition activates a pathway that branches from the canonical amino acid response in mammalian cells. Proc Natl Acad Sci U S A. 2020 Apr 21;117(16):8900-8911. doi: 10.1073/pnas.1913788117. Epub 2020 Apr 6. [PubMed:32253314 ]
- Curran SC, Pereira JH, Baluyot MJ, Lake J, Puetz H, Rosenburg DJ, Adams P, Keasling JD: Structure and Function of BorB, the Type II Thioesterase from the Borrelidin Biosynthetic Gene Cluster. Biochemistry. 2020 Apr 28;59(16):1630-1639. doi: 10.1021/acs.biochem.0c00126. Epub 2020 Apr 13. [PubMed:32250597 ]
- LOTUS database [Link]
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