Coumermycin A1
Chemical compound
- none
- 3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(4-hydroxy-8-methyl-2-oxo-2H-chromene-3,7-diyl)oxy(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate
- 4434-05-3
Y
- 54675768
- 16736904
N
- PCH9QZ1IIH
- CHEBI:3907
N
- ChEMBL389471
N
- DTXSID901023379
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- CO[C@@H]1[C@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4c[nH]c(C(=O)Nc5c(=O)oc6c(C)c(ccc6c5O)O[C@@H]5OC(C)(C)[C@H](OC)[C@H](OC(=O)c6ccc(C)[nH]6)[C@H]5O)c4C)c(=O)oc3c2C)OC1(C)C
InChI
- InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
N
- Key:WTIJXIZOODAMJT-DHFGXMAYSA-N
N
![☒](http://upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png)
![check](http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)
Coumermycin A1 is an aminocoumarin.[1][2] Its main target is the ATPase site of the DNA gyrase GyrB subunit.[3]
See also
- Chemically induced dimerization
References
- ^ Heide L (2009). "Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins". Biotechnology Advances. 27 (6): 1006–1014. doi:10.1016/j.biotechadv.2009.05.017. PMID 19463934.
- ^ Heide L, Gust B, Anderle C, Li SM (2008). "Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics". Current Topics in Medicinal Chemistry. 8 (8): 667–79. doi:10.2174/156802608784221505. PMID 18473891.
- ^ Vanden Broeck A, McEwen AG, Chebaro Y, Potier N, Lamour V (April 2019). "Structural Basis for DNA Gyrase Interaction with Coumermycin A1". Journal of Medicinal Chemistry. 62 (8): 4225–4231. doi:10.1021/acs.jmedchem.8b01928. PMID 30920824.
- v
- t
- e
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor | |||||||||
---|---|---|---|---|---|---|---|---|---|
Sulfonamides (DHPS inhibitor) |
| ||||||||
Combinations |
| ||||||||
Other DHPS inhibitors |
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
1st generation | |||||||||
---|---|---|---|---|---|---|---|---|---|
Fluoroquinolones |
| ||||||||
Newer non-fluorinated | |||||||||
Related (DG) |
inhibitors
Nitroimidazole derivatives |
---|
Rifamycins/ RNA polymerase | |
---|---|
Lipiarmycins |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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- v
- t
- e