Compound ID | 2718

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Rifamazine

Class: Rifamycin

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: RNA synthesis inhibitor. Targets DNA-dependent RNA polymerase (RNA synthesis inhibitor)
Target Pathogen: Active against Staphylococcus aureus
Description: Semisynthetic compound; dimeric rifamycin
Institute where first reported: Department for Antibiotics and Natural Products of Lepetit; Laboratori di Microbiologia, Gruppo Lepetit S.p.A., Via Durando 38, 1-20158 Milano, Italy
Year first mentioned: 1975
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1447.57
Iso. SMILES: CO[C@H]1/C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C(C=NN=CC=5C=6NC(=O)/C(=C\C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)C)[C@H](C)[C@@H](OC)/C=C\O[C@@]7(C)OC8=C(C7=O)C(C5O)=C(C(O)=C8C)C6O)/C)=C(NC(=O)/C(=C\C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)C)[C@@H]1C)/C)C(O)=C4C(O)=C3C
InChI Key: OHRPJAALPNBKCL-BWHOGDMWSA-N
Can. SMILES: C[C@H]1/C=C\C=C(\C)/C(=O)NC2=C(C3=C(C(=C4C(=C3C(=C2C=NN=CC5=C(C6=C7C8=C(C)C(=C6C(=C5NC(=O)/C(=C\C=C/[C@H](C)[C@@H]([C@@H](C)[C@H]([C@@H](C)[C@@H]([C@H](C)[C@H](/C=C\O[C@](C)(C7=O)O8)OC)OC(=O)C)O)O)/C)O)O)O)O)C(=O)[C@@](C)(O/C=C\[C@@H]([C@@H](C)[C@H]([C@H](C)[C@@H]([C@H](C)[C@H]1O)O)OC(=O)C)OC)O4)C)O)O
InChI: InChI=1S/C76H94N4O24/c1-31-21-19-23-33(3)73(95)79-55-45(63(89)49-51(65(55)91)61(87)41(11)69-53(49)71(93)75(15,103-69)99-27-25-47(97-17)35(5)67(101-43(13)81)39(9)59(85)37(7)57(31)83)29-77-78-30-46-56-66(92)52-50(64(46)90)54-70(42(12)62(52)88)104-76(16,72(54)94)100-28-26-48(98-18)36(6)68(102-44(14)82)40(10)60(86)38(8)58(84)32(2)22-20-24-34(4)74(96)80-56/h19-32,35-40,47-48,57-60,67-68,83-92H,1-18H3,(H,79,95)(H,80,96)/b21-19-,22-20-,27-25-,28-26-,33-23-,34-24-,77-29?,78-30?/t31-,32-,35+,36+,37+,38+,39+,40+,47-,48-,57-,58-,59+,60+,67+,68+,75-,76-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/substance/275180757
Citation: https://febs.onlinelibrary.wiley.com/doi/10.1111/j.1432-1033.1975.tb04007.x

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