(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编号: 132480
• 分子式: C55H59N5O20
• 平均质量: 1110.07846
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: (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
• 别名: Coumermycin A1

登记号

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

理论计算性质

• Acid pKa: 6.685806
• 质子受体: 16
• 质子供体: 9
• LogD (pH = 5.5): 4.364195
• LogD (pH = 7.4): 3.28575
• Log P: 4.392013
• 摩尔折射率: 281.2201 cm^3
• 极化性: 107.22563 Å^3
• 极化表面积: 347.07 Å^2
• 可自由旋转的化学键: 16
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: UX9375000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

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

详细说明

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