Coumermycin A1

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 387419821

| IUPAC_name = 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

| image = Coumermycin A1.svg

| tradename =

| pregnancy_AU =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 4434-05-3

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = PCH9QZ1IIH

| ATC_prefix = none

| ATC_suffix =

| PubChem = 54675768

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 389471

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 3907

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 16736904

| C=55 | H=59 | N=5 | O=20

| smiles = 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = WTIJXIZOODAMJT-DHFGXMAYSA-N

| synonyms = Coumamycin

}}

Coumermycin A1 is an aminocoumarin.{{cite journal | vauthors = Heide L | title = Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins | journal = Biotechnology Advances | volume = 27 | issue = 6 | pages = 1006–1014 | year = 2009 | pmid = 19463934 | doi = 10.1016/j.biotechadv.2009.05.017 }}{{cite journal | vauthors = Heide L, Gust B, Anderle C, Li SM | title = Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics | journal = Current Topics in Medicinal Chemistry | volume = 8 | issue = 8 | pages = 667–79 | year = 2008 | pmid = 18473891 | doi = 10.2174/156802608784221505 }} Its main target is the ATPase site of the DNA gyrase GyrB subunit.{{cite journal | vauthors = Vanden Broeck A, McEwen AG, Chebaro Y, Potier N, Lamour V | title = Structural Basis for DNA Gyrase Interaction with Coumermycin A1 | journal = Journal of Medicinal Chemistry | volume = 62 | issue = 8 | pages = 4225–4231 | date = April 2019 | pmid = 30920824 | doi = 10.1021/acs.jmedchem.8b01928 | doi-access = free }}