Compound ID | 1505

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Vancomycin

Class: Glycopeptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Broad Gram-positive activity including anaerobes
Description: Natural product from Amycolatopsis orientalis (formerly Streptomyces orientalis
Institute where first reported: FDA, USA; ANI Pharmaceuticals
Year first mentioned: 1956
Highest development stage: Approved by FDA in 1986
Development status: Approved
Reason dropped: Other formulations were discontinued
Chemical structure(s):
Click here for structure editor
Molecular weight: 1449.26
Iso. SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C%10=CC(=C(O4)C=C%10)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChI Key: MYPYJXKWCTUITO-LYRMYLQWSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@@H]1[C@@H](C2=CC=C(C(=C2)Cl)OC3=CC4=CC(=C3O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@H]6C[C@@](C)([C@@H]([C@H](C)O6)O)N)OC7=CC=C(C=C7Cl)[C@H]([C@H]8C(=O)N[C@@H](C9=CC(=CC(=C9C%10=CC(=CC=C%10O)[C@H](C(=O)N8)NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)O)O)C(=O)O)O)O)NC
InChI: InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/14969
Guide to Pharmacology: vancomycin
Citations:
  • https://www.europeanreview.org/article/8585
  • https://doi.org/10.1086/491709

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