CHEBI:28001 - vancomycin

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ChEBI Name vancomycin
ChEBI ID CHEBI:28001
Definition A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:49941, CHEBI:9931, CHEBI:27276
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Formula C66H75Cl2N9O24
Net Charge 0
Average Mass 1449.25336
Monoisotopic Mass 1447.43020
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
InChIKey MYPYJXKWCTUITO-LYRMYLQWSA-N
SMILES CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]5NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c1ccc(O)c(c1)-c1c(O)cc(O)cc1[C@H](NC5=O)C(O)=O)c3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1)c(Cl)c2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vancomycin (CHEBI:28001) has functional parent vancomycin aglycone (CHEBI:47724)
vancomycin (CHEBI:28001) has role antibacterial drug (CHEBI:36047)
vancomycin (CHEBI:28001) has role antimicrobial agent (CHEBI:33281)
vancomycin (CHEBI:28001) has role bacterial metabolite (CHEBI:76969)
vancomycin (CHEBI:28001) is a glycopeptide (CHEBI:24396)
vancomycin (CHEBI:28001) is conjugate base of vancomycin(1+) (CHEBI:76842)
Incoming telavancin (CHEBI:71229) has functional parent vancomycin (CHEBI:28001)
vancomycin(1+) (CHEBI:76842) is conjugate acid of vancomycin (CHEBI:28001)
IUPAC Name
(3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyloxy]-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid
INNs Sources
vancomicina ChemIDplus
vancomycin ChemIDplus
vancomycine ChemIDplus
vancomycinum ChemIDplus
Synonyms Sources
(1S,2R,18R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-48-[2-O-(3-amino-2,3,6-trideoxy-3-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyloxy]-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[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),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid ChEBI
(2.2Sp,3.5Sa,2.6Sp)-O4.2,C3.4:C5.4,O4.6:C3.5,C2.7-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-β-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-β-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine] JCBN
vancomicin
Note: (2015-03-23) An uncommon spelling variant.
 ChEBI
Vancomycin KEGG COMPOUND
VANCOMYCIN PDBeChem
Brand Name Source
Vancocin KEGG DRUG
Manual Xrefs Databases
2807 DrugCentral
C00016052 KNApSAcK
C06689 KEGG COMPOUND
CPD-12245 MetaCyc
D00212 KEGG DRUG
DB00512 DrugBank
US3067099 Patent
VAN PDBeChem
Vancomycin Wikipedia
View more database links
Registry Numbers Types Sources
1404-90-6 CAS Registry Number KEGG COMPOUND
1404-90-6 CAS Registry Number ChemIDplus
3132 Beilstein Registry Number Beilstein
3132 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017
General Comment
2015-04-23 Vancomycin is a member of the class of glycopeptide antibiotics.