Compound ID | 460

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Coumamidine Gamma 1

Synonym(s): Coumamidine γ1

Class: Aminoglycoside

Agent Type: Natural product; Small molecule;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Unknown
Propensity to select resistant mutants: Low frequency of resistance
Description: Natural product from Saccharopolyspora sp. AB1167L-65; not absorbed orally in mouse infection model
Institute where first reported: Abbott Laboratories
Year first mentioned: 1988
Development status: Experimental
Reason dropped: Needs to be administered subcutaneously as not absorbed through oral administration as observed in mouse model
Chemical structure(s):
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Molecular weight: 835.82
Iso. SMILES: CC1C(C(C(C(O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCC(=N)N)N=C(N)N)O)NC(=O)NC3C(C(C(CO3)OC4COC5C(C4O)N(C(=O)N5)C(=O)N)O)NC(=O)N
InChI Key: RALPRAPANVNIPH-QPJJXVBHSA-N
Can. SMILES: CC1C(C(C(C(O1)OC2=CC=C(C=C2)/C=C/C(=O)NCCC(=N)N)N=C(N)N)O)NC(=O)NC3C(C(C(CO3)OC4COC5C(C4O)N(C(=O)N)C(=O)N5)O)NC(=O)N
InChI: InChI=1S/C33H49N13O13/c1-12-19(25(50)21(41-29(36)37)28(57-12)58-14-5-2-13(3-6-14)4-7-18(47)40-9-8-17(34)35)43-32(53)44-26-20(42-30(38)51)23(48)15(10-55-26)59-16-11-56-27-22(24(16)49)46(31(39)52)33(54)45-27/h2-7,12,15-16,19-28,48-50H,8-11H2,1H3,(H3,34,35)(H2,39,52)(H,40,47)(H,45,54)(H4,36,37,41)(H3,38,42,51)(H2,43,44,53)/b7-4+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6443955
Citations:
  • https://doi.org/10.7164/antibiotics.42.533
  • https://doi.org/10.7164/antibiotics.42.538
  • https://doi.org/10.7164/antibiotics.42.527

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