Compound ID | 2371

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Mannopeptimycin

Synonym(s): Antibiotic ac-98

Class: Glycopeptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Sequesters lipid II preventing transglycosylation step in cell wall synthesis
Target Pathogen: Active against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci
Description: Natural product from Streptomyces hygroscopicus
Institute where first reported: Wyeth Holdings LLC, American Cyanamid Co
Year first mentioned: 1970
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1367.37
Iso. SMILES: C[C@H]([C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N1)CO)[C@H]([C@@H]2CNC(=[N+]2[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)O)O)O)O)N)O)[C@H]([C@@H]4C[NH+]=C(N4)N)O)CC5=CC=C(C=C5)O[C@@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)CO)O)OC(=O)CC(C)C)O)O)O)C8=CC=CC=C8
InChI Key: HBTVDBLISZYTGP-ONIHXMSRSA-P
Can. SMILES: CC(C)CC(=O)O[C@H]1[C@@H]([C@@H](CO)O[C@@H]([C@H]1O)O[C@@H]2[C@@H](CO)O[C@@H]([C@H]([C@H]2O)O)OC3=CC=C(C=C3)C[C@@H]4C(=O)N[C@@H]([C@H]([C@@H]5C[NH+]=C(N)N5)O)C(=O)N[C@H]([C@H]([C@@H]6CNC(=[N+]6[C@@H]7[C@H]([C@H]([C@@H]([C@@H](O)O7)O)O)O)N)O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)C8=CC=CC=C8)C(=O)N4)O
InChI: InChI=1S/C58H84N12O26/c1-21(2)13-33(75)94-47-39(78)30(19-72)92-56(45(47)84)95-46-31(20-73)93-55(44(83)41(46)80)91-25-11-9-23(10-12-25)14-26-49(86)68-35(37(76)27-15-62-57(59)66-27)52(89)69-36(38(77)29-16-63-58(60)70(29)53-42(81)40(79)43(82)54(90)96-53)51(88)65-28(18-71)48(85)61-17-32(74)67-34(50(87)64-26)22(3)24-7-5-4-6-8-24/h4-12,21-22,26-31,34-47,53-56,71-73,76-84,90H,13-20H2,1-3H3,(H11,59,60,61,62,63,64,65,66,67,68,69,74,85,86,87,88,89)/p+2/t22-,26+,27-,28-,29-,30+,31+,34-,35-,36+,37-,38-,39+,40+,41+,42-,43-,44-,45-,46+,47-,53-,54-,55-,56+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/90658418
Citations:
  • https://journals.asm.org/doi/10.1128/aac.48.3.728-738.2004
  • https://pubs.acs.org/doi/10.1021/jacs.1c05922
  • https://journals.asm.org/doi/10.1128/aac.47.1.62-69.2003
    • Patent: US3495004A

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