vancomycin

CHEBI:28001 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

glycopeptide antibioticARO:3000081

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24396 CHEBI:24396
ARO:3000081 ARO:3000081

Chemical structure

Computed structure properties
Molecular formula	C66H75Cl2N9O24
Charge	0
Average mass	1449.271 Da
Monoisotopic mass	1447.4302 Da
Source	ChEBI
InChIKey	MYPYJXKWCTUITO-LYRMYLQWSA-N

SMILES

CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O

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

Also called

Vancocin (BRAND_NAME)— chebi
vancomicina (INN)— chebi
vancomycine (INN)— chebi
vancomycinum (INN)— chebi
(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 (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— 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] (EXACT_SYNONYM)— chebi
VANCOMYCIN (EXACT_SYNONYM)— chebi
Vancomycin (EXACT_SYNONYM)— chebi
vancomicin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000028
cas:1404-90-6
drugbank:DB00512
drugcentral:2807
kegg.compound:C06689
kegg.drug:D00212
knapsack:C00016052
metacyc.compound:CPD-12245
patent:US3067099
pdb-ccd:VAN
reaxys:3132
wikipedia.en:Vancomycin
chembl:CHEMBL262777
pubchem.compound:14969

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:0000028`	vancomycin	`antibioticmech:aro-aab2a8f06b`	2026-08-30
CHEBI	`CHEBI:28001`	vancomycin	`antibioticmech:chebi-b6a7496b60`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

acyl-D-alanyl-D-alanine CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3000720

CARD/ARO database assertion; target organism, strain, and assay are not specified. The D-Ala-D-Ala chemical group is bound as a cell-wall precursor component. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000720 (CARD/ARO asserts targeted_by_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

20 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 18

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Clostridioides difficile murG with mutation conferring resistance to vancomycin	ARO:3004561	not organism-specific	—	ARO:3004561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
Clostridioides difficile rpoC with mutation conferring resistance to vancomycin	ARO:3004681	not organism-specific	—	ARO:3004681 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
D-Ala-D-Ala ligase	ARO:3003970	not organism-specific	—	ARO:3003970 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
cfr(D)	ARO:3005021	not organism-specific	—	ARO:3005021 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanA	ARO:3000236	not organism-specific	—	ARO:3000236 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanB	ARO:3000238	not organism-specific	—	ARO:3000238 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanC	ARO:3000246	not organism-specific	—	ARO:3000246 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanD	ARO:3000253	not organism-specific	—	ARO:3000253 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanE	ARO:3000259	not organism-specific	—	ARO:3000259 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanF	ARO:3000255	not organism-specific	—	ARO:3000255 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanG	ARO:3000257	not organism-specific	—	ARO:3000257 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanI	ARO:3003722	not organism-specific	—	ARO:3003722 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanL	ARO:3000260	not organism-specific	—	ARO:3000260 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanM	ARO:3000256	not organism-specific	—	ARO:3000256 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanN	ARO:3002917	not organism-specific	—	ARO:3002917 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanO	ARO:3002918	not organism-specific	—	ARO:3002918 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster vanP	ARO:3007187	not organism-specific	—	ARO:3007187 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
murG transferase	ARO:3004560	not organism-specific	—	ARO:3004560 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
VRA-F	ARO:3007843	not organism-specific	—	ARO:3007843 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)
mlaFEDB	ARO:3005058	not organism-specific	—	ARO:3005058 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000028 (vancomycin); database assertion, not a primary citation.)

Producer organisms

Organisms that biosynthesize this compound.

Producer organisms
Organism	BGC	Source	Quality	Note	Evidence
Amycolatopsis orientalis `NCBITaxon:1156913` strain HCCB10007 (ATCC43491)	BGC0000455	MIBIG 4.0.1 (entry 6); reviewed	questionable	MIBiG active entry with a non-placeholder expert reviewer; compound 'vancomycin' joined by exact Standard InChIKey.	DOI:10.1021/ja00361a029 (MIBiG attaches this reference to the compound itself, so it supports the producer/compound link this item asserts.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.