Compound ID | 2721

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Rubradirin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: RNA synthesis inhibitor. Binds to RNA polymerase
Target Pathogen: Active against multidrug-resistant and -susceptible Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, and Streptococcus viridans
Description: Natural product from Streptomyces achromogenes var. rubradiris; ansamycin-type
Institute where first reported: The Upjohn Company, MI USA
Year first mentioned: 1965
Development status: Experimental
Chemical structure(s):
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Molecular weight: 998.9
Iso. SMILES: CC1/C=C(/C(=O)C2=C(C(=CC3=C2C(=O)C4=C(C3=O)NCC(O4)(C(=O)C(C1OC(=O)C5=C(C(=CC(=N5)C(=O)NC6=C(C7=C(C=C(C=C7)OC)OC6=O)O)OC8CC(C(C(O8)C)OC)(C)[N+](=O)[O-])O)O)C)C)O)\C
InChI Key: GBZJIWQNTNUYGZ-GZTJUZNOSA-N
Can. SMILES: C/C/1=C\C(C)C(C(C(=O)C2(C)CNC3=C(C(=O)C4=C(C1=O)C(=C(C)C=C4C3=O)O)O2)O)OC(=O)C5=C(C(=CC(=N5)C(=O)NC6=C(C7=C(C=C(C=C7)OC)OC6=O)O)OC8CC(C)(C(C(C)O8)OC)[N+](=O)[O-])O
InChI: InChI=1S/C48H46N4O20/c1-17-11-19(3)40(39(59)42(60)48(6)16-49-30-36(56)23-12-18(2)34(54)29(33(17)53)28(23)38(58)41(30)72-48)71-46(63)32-37(57)26(69-27-15-47(5,52(64)65)43(67-8)20(4)68-27)14-24(50-32)44(61)51-31-35(55)22-10-9-21(66-7)13-25(22)70-45(31)62/h9-14,19-20,27,39-40,43,49,54-55,57,59H,15-16H2,1-8H3,(H,51,61)/b17-11+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54711001
Citations:
  • https://www.jstage.jst.go.jp/article/antibiotics1968/32/11/32_11_1186/_pdf
  • https://www.jstage.jst.go.jp/article/antibiotics1968/45/8/45_8_1313/_pdf
  • https://www.sciencedirect.com/science/article/pii/S1016847823133577
  • https://link.springer.com/article/10.1007/s00203-007-0337-3#Bib1

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