Coumermycin A1 - Misplaced Pages

(Redirected from Coumermycin) Chemical compound Pharmaceutical compound

Coumermycin A1
Clinical data

Other names	Coumamycin
ATC code	none
Identifiers
IUPAC name 3-methyl-1H-pyrrole-2,4-diyl)bis bis(5-methyl-1H-pyrrole-2-carboxylate
CAS Number	4434-05-3
PubChem CID	54675768
ChemSpider	16736904
UNII	PCH9QZ1IIH
ChEBI	CHEBI:3907
ChEMBL	ChEMBL389471
CompTox Dashboard (EPA)	DTXSID901023379
ECHA InfoCard	100.164.703
Chemical and physical data
Formula	C₅₅H₅₉N₅O₂₀
Molar mass	1110.092 g·mol
3D model (JSmol)	Interactive image
SMILES CO1(OC(=O)c2ccc(C)2)(O)(Oc2ccc3c(O)c(NC(=O)c4cc(C(=O)Nc5c(=O)oc6c(C)c(ccc6c5O)O5OC(C)(C)(OC)(OC(=O)c6ccc(C)6)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 Key:WTIJXIZOODAMJT-DHFGXMAYSA-N
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Coumermycin A1 is an aminocoumarin. Its main target is the ATPase site of the DNA gyrase GyrB subunit.

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.

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine, Sulfadimerazine, Sulfadimezine) Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

2nd generation	Ciprofloxacin Ofloxacin Enoxacin Fleroxacin Lomefloxacin Nadifloxacin/Levonadifloxacin/Alalevonadifloxacin Norfloxacin Pefloxacin Rufloxacin
3rd generation	Levofloxacin Balofloxacin Grepafloxacin Pazufloxacin Sparfloxacin Temafloxacin Tosufloxacin
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin Garenoxacin Prulifloxacin Sitafloxacin Trovafloxacin/Alatrofloxacin
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Related (DG)

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

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