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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| IUPAC_name = oxy-8-methyl-4-oxochromen-3-yl]carbamoyl]-3-methyl-1''H''-pyrrole-2-carbonyl]amino]-8-methyl-4-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1''H''-pyrrole-2-carboxylate |
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| Watchedfields = changed |
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| image = Coumermycin A1.png |
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| verifiedrevid = 387419821 |
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| synonyms = Coumamycin |
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| IUPAC_name = 3-methyl-1''H''-pyrrole-2,4-diyl)bis bis(5-methyl-1''H''-pyrrole-2-carboxylate |
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| CAS_number = 4434-05-3 |
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| image = Coumermycin A1.svg |
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| ATC_prefix = none |
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| ATC_suffix = |
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<!--Clinical data--> |
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| PubChem = 451651 |
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| tradename = |
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| DrugBank = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| chemical_formula = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 4434-05-3 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = PCH9QZ1IIH |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 54675768 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 389471 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 3907 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 16736904 |
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<!--Chemical data--> |
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| C=55 | H=59 | N=5 | O=20 |
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| C=55 | H=59 | N=5 | O=20 |
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| 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 |
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| molecular_weight = 1110.08 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| smiles = CC1=CC=C(N1)C(=O)O2(C(OC(2OC)(C)C)OC3=C(C4=C(C=C3)C(=O)C(=C(O4)O)NC(=O)C5=CNC(=C5C)C(=O)NC6=C(OC7=C(C6=O)C=CC(=C7C)OC8(((C(O8)(C)C)OC)OC(=O)C9=CC=C(N9)C)O)O)C)O |
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| 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 |
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| bioavailability = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| protein_bound = |
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| StdInChIKey = WTIJXIZOODAMJT-DHFGXMAYSA-N |
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| metabolism = |
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| synonyms = Coumamycin |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Coumermycin A1''' is an ].<ref>{{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 }}</ref><ref>{{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 }}</ref> Its main target is the ] site of the ] GyrB subunit.<ref>{{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 }}</ref> |
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'''Coumermycin A1''' is an ].<ref>{{cite pmid|19463934}}</ref><ref>{{cite pmid|18473891}}</ref> |
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==References== |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{antibiotic-stub}} |
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{{Nucleic acid inhibitors}} |
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{{Nucleic acid inhibitors}} |
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] |
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{{antibiotic-stub}} |