(3R,4S,5R,6R)-5-hydroxy-6-[(4-hydroxy-3-{5-[(4-hydroxy-7-{[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyloxy)oxan-2-yl]oxy}-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl]-4-methyl-1H-pyrrole-3-amido}-8-methyl-2-oxo-2H-chromen-7-yl)oxy]-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate

• ChemBase ID: 132480
• Molecular Formular: C55H59N5O20
• Molecular Mass: 1110.07846
• Monoisotopic Mass: 1109.37533931
• SMILES: Cc1ccc([nH]1)C(=O)O[C@H]1[C@H]([C@@H](OC([C@@H]1OC)(C)C)Oc1ccc2c(c(c(=O)oc2c1C)NC(=O)c1c[nH]c(c1C)C(=O)Nc1c(c2ccc(c(c2oc1=O)C)O[C@H]1[C@@H]([C@@H]([C@H](C(O1)(C)C)OC)OC(=O)c1ccc([nH]1)C)O)O)O)O
• Canonical SMILES: CO[C@@H]1[C@@H](OC(=O)c2ccc([nH]2)C)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1C)oc(=O)c(c2O)NC(=O)c1c[nH]c(c1C)C(=O)Nc1c(=O)oc2c(c1O)ccc(c2C)O[C@@H]1OC(C)(C)[C@@H]([C@H]([C@H]1O)OC(=O)c1ccc([nH]1)C)OC
• 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
• InChIKey: WTIJXIZOODAMJT-DHFGXMAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-5-hydroxy-6-[(4-hydroxy-3-{5-[(4-hydroxy-7-{[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyloxy)oxan-2-yl]oxy}-8-methyl-2-oxo-2H-chromen-3-yl)carbamoyl]-4-methyl-1H-pyrrole-3-amido}-8-methyl-2-oxo-2H-chromen-7-yl)oxy]-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate
• IUPAC Traditional name: (3R,4S,5R,6R)-5-hydroxy-6-[(4-hydroxy-3-{5-[(4-hydroxy-7-{[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyloxy)oxan-2-yl]oxy}-8-methyl-2-oxochromen-3-yl)carbamoyl]-4-methyl-1H-pyrrole-3-amido}-8-methyl-2-oxochromen-7-yl)oxy]-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate
• Synonyms: Coumermycin A1

Database IDs

• CAS Number: 4434-05-3
• MDL Number: MFCD00057312
• Beilstein Number: 470805
• PubChem SID: 162226757
• PubChem CID: 54675768

CALCULATED PROPERTIES

• Acid pKa: 6.685806
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): 4.364195
• LogD (pH = 7.4): 3.28575
• Log P: 4.392013
• Molar Refractivity: 281.2201 cm^3
• Polarizability: 107.22563 Å^3
• Polar Surface Area: 347.07 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: UX9375000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C55H59N5O20

DETAILS

Sigma Aldrich - C9270

Biochem/physiol Actions
Coumermycin A1 inhibits DNA Gyrase which thereby inhibits cell division in bacteria1.
Application
Coumermycin A1 is an aminocoumarin antibiotic used to study processes such as DNA replication, transcription, and recombination that involve DNA topoisomerase II activity. It has been used to treat Staphylococcus aureus endocarditis in the rat model1 and to study the effect of coumermycin A1 on the expression of 67 fusions in Salmonella typhimurium. 2.
Coumermycin A1 is used to study processes such as DNA replication, transcription, and recombination that involve DNA topoisomerase II activity.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9270.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 27715

Other Notes
Preferential inhibitor of replicative DNA synthesis in E. coli1