Record Information |
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Version | 2.0 |
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Created at | 2022-09-07 21:46:49 UTC |
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Updated at | 2022-09-07 21:46:50 UTC |
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NP-MRD ID | NP0256826 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2e)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4e,6e,12e,14z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-6-isopropyl-5-methyloxan-4-yl)oxy]-4-oxobut-2-enoic acid |
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Description | Bafilomycin C1 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. (2e)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4e,6e,12e,14z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-6-isopropyl-5-methyloxan-4-yl)oxy]-4-oxobut-2-enoic acid is found in Streptomyces griseus. It was first documented in 2016 (PMID: 27608853). Based on a literature review a significant number of articles have been published on Bafilomycin C1 (PMID: 29134406) (PMID: 33636028) (PMID: 29752478) (PMID: 29391532). |
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Structure | COC1\C=C\C=C(C)\CC(C)C(O)C(C)\C=C(/C)\C=C(OC)\C(=O)OC1C(C)C(O)C(C)C1(O)CC(OC(=O)\C=C\C(O)=O)C(C)C(O1)C(C)C InChI=1S/C39H60O12/c1-21(2)36-26(7)31(49-33(42)16-15-32(40)41)20-39(46,51-36)28(9)35(44)27(8)37-29(47-10)14-12-13-22(3)17-24(5)34(43)25(6)18-23(4)19-30(48-11)38(45)50-37/h12-16,18-19,21,24-29,31,34-37,43-44,46H,17,20H2,1-11H3,(H,40,41)/b14-12+,16-15+,22-13+,23-18+,30-19- |
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Synonyms | Value | Source |
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Bafilomycin-C1 | MeSH |
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Chemical Formula | C39H60O12 |
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Average Mass | 720.8970 Da |
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Monoisotopic Mass | 720.40848 Da |
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IUPAC Name | (2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-5-methyl-6-(propan-2-yl)oxan-4-yl)oxy]-4-oxobut-2-enoic acid |
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Traditional Name | (2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-6-isopropyl-5-methyloxan-4-yl)oxy]-4-oxobut-2-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1\C=C\C=C(C)\CC(C)C(O)C(C)\C=C(/C)\C=C(OC)\C(=O)OC1C(C)C(O)C(C)C1(O)CC(OC(=O)\C=C\C(O)=O)C(C)C(O1)C(C)C |
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InChI Identifier | InChI=1S/C39H60O12/c1-21(2)36-26(7)31(49-33(42)16-15-32(40)41)20-39(46,51-36)28(9)35(44)27(8)37-29(47-10)14-12-13-22(3)17-24(5)34(43)25(6)18-23(4)19-30(48-11)38(45)50-37/h12-16,18-19,21,24-29,31,34-37,43-44,46H,17,20H2,1-11H3,(H,40,41)/b14-12+,16-15+,22-13+,23-18+,30-19- |
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InChI Key | WUDBXVQNMOTFEE-FUGNQFJWSA-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
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Oxane
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Hemiacetal
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Dialkyl ether
- Ether
- Oxacycle
- Organoheterocyclic compound
- Carbonyl group
- Alcohol
- Organic oxide
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen 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 | - Mevers E, Sauri J, Liu Y, Moser A, Ramadhar TR, Varlan M, Williamson RT, Martin GE, Clardy J: Homodimericin A: A Complex Hexacyclic Fungal Metabolite. J Am Chem Soc. 2016 Sep 28;138(38):12324-7. doi: 10.1021/jacs.6b07588. Epub 2016 Sep 16. [PubMed:27608853 ]
- Mevers E, Chouvenc T, Su NY, Clardy J: Chemical Interaction among Termite-Associated Microbes. J Chem Ecol. 2017 Dec;43(11-12):1078-1085. doi: 10.1007/s10886-017-0900-6. Epub 2017 Nov 13. [PubMed:29134406 ]
- Zhu C, Lew CI, Neuhaus GF, Adpressa DA, Zakharov LN, Kaweesa EN, Plitzko B, Loesgen S: Biodiversity, Bioactivity, and Metabolites of High Desert Derived Oregonian Soil Bacteria. Chem Biodivers. 2021 Apr;18(4):e2100046. doi: 10.1002/cbdv.202100046. Epub 2021 Mar 24. [PubMed:33636028 ]
- Gao X, Han L, Ding N, Mu Y, Guan P, Hu C, Huang X: Bafilomycin C1 induces G0/G1 cell-cycle arrest and mitochondrial-mediated apoptosis in human hepatocellular cancer SMMC7721 cells. J Antibiot (Tokyo). 2018 Sep;71(9):808-817. doi: 10.1038/s41429-018-0066-7. Epub 2018 May 11. [PubMed:29752478 ]
- Su H, Han L, Ding N, Guan P, Hu C, Huang X: Bafilomycin C1 exert antifungal effect through disturbing sterol biosynthesis in Candida albicans. J Antibiot (Tokyo). 2018 Mar;71(4):467-476. doi: 10.1038/s41429-017-0009-8. Epub 2018 Feb 1. [PubMed:29391532 ]
- LOTUS database [Link]
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