ванкомицин

Also known as (2.2Sp,3.5sa,2.6sp)-O(4.2),C(3.4), Vancocin, c(5.4),O(4.6), Vancomycinum, Vancomicina, Vancomycine

антибиотик из группы трициклических гликопептидов

OverviewAI-generated

Vancomycin is a chemical compound with the formula C₆₆H₇₅Cl₂N₉O₂₄. It has a mass of 1447.43 and a defined daily dose of 2. The substance carries a charge of 0 and features an xlogp value of -2.6. Its topological polar surface area is 530, with 19 hydrogen bond donors and 26 hydrogen bond acceptors.

The compound is associated with the NCI Thesaurus ID C925 and MCN codes 3003.20.71 and 3004.20.71. A search for vancomycin on PubMed yields 43478 results. The subject is referenced by 431 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C66H75Cl2N9O24
Molecular weight: 1449.2 g/mol
IUPAC name: (1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
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](C1=CC(=C(O4)C=C1)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
InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N
XLogP: -2.6
Polar surface area: 530 Å²
H-bond donors: 19
H-bond acceptors: 26
Formal charge: 0

via PubChem

Research

43,478 papers

Vancomycin.Mayo Clinic proceedings · 1991
Renaissance of vancomycin: approaches for breaking antibiotic resistance in multidrug-resistant bacteria.Canadian journal of microbiology · 2020
The pharmacokinetic and pharmacodynamic properties of vancomycin.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2006
Vancomycin mimicry: towards new supramolecular antibiotics.Organic & biomolecular chemistry · 2022
Vancomycin.The Medical clinics of North America · 1995

via PubMed

Wikidata facts

Subclass of: glycopeptide
Mass: 1447.43
Has use: medication

Show 13 more facts

chemical formula: C₆₆H₇₅Cl₂N₉O₂₄
found in taxon: Nostoc
medical condition treated: septic arthritis
defined daily dose: 2
Commons category: Vancomycin
canonical SMILES: CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
isomeric SMILES: CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]5C[C@](C)(N)[C@H](O)[C@H](C)O5)C6=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]7C8=CC=C(O)C(=C8)C9=C(O)C=C(O)C=C9[C@H](NC(=O)[C@@H](NC7=O)[C@H](O)C%10=CC=C(O6)C(Cl)=C%10)C(O)=O)C(Cl)=C2
NCI Thesaurus ID: C925
subject has role: bactericide
MCN code: 3004.20.71
has characteristic: bitterness
significant drug interaction: tobramycin
legal status (medicine): boxed warning