oritavancin

CHEBI:82699 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A semisynthetic glycopeptide used (as its bisphosphate salt) for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA. — ChEBI

Classification

glycopeptide antibioticARO:3000081

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:24396
Label unavailable CHEBI:63353
Label unavailable CHEBI:72588
glycopeptide antibiotic ARO:3000081

Chemical structure

Computed structure properties
Molecular formula	C86H97Cl3N10O26
Charge	0
Average mass	1793.125 Da
Monoisotopic mass	1790.56411 Da
Source	ChEBI
InChIKey	VHFGEBVPHAGQPI-LXKZPTCJSA-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[C@H]3C[C@](C)(N)[C@@H](O)[C@H](C)O3)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)(NCc3ccc(-c4ccc(Cl)cc4)cc3)[C@@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O

InChI

InChI=1S/C86H97Cl3N10O26/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-/m0/s1

Also called

(4''R)-22-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabinohexopyranosyl)-N3''-(p-(p-chlorophenyl)benzyl)vancomycin (EXACT_SYNONYM)— chebi
(4''R)-22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabino-hexopyranosyl)-N3''-((4'-chloro(1,1'-biphenyl)-4-yl)methyl)vancomycin (EXACT_SYNONYM)— chebi
Chlorobiphenyl-chloroeremomycin (EXACT_SYNONYM)— chebi
LY333328 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

drugcentral:4678

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Oritavancin

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial drug 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:3000189`	oritavancin	`antibioticmech:aro-8dca94eafb`	2026-08-30
CHEBI	`CHEBI:82699`	oritavancin	`antibioticmech:chebi-76816de773`	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:3000189 (oritavancin); database assertion, not a primary citation.)

pentaglycyl bridge CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3000726

CARD/ARO database assertion; target organism, strain, and assay are not specified. The pentaglycyl bridge is a peptidoglycan component rather than a protein. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000726 (CARD/ARO asserts targeted_by_antibiotic ARO:3000189 (oritavancin); database assertion, not a primary citation.)

peptidoglycan D-Ala-D-Ala termini and pentaglycyl bridges CELL_WALL_COMPONENT DIRECT_BINDING_TARGET

Solid-state NMR on selectively labeled intact cells established cell-wall binding and compared transglycosylation and transpeptidation inhibition. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2008-01 (retrieved 2026-09-02).

Staphylococcus aureus NCBITaxon:1280

PMID:18258256 (Primary intact-cell solid-state NMR mechanism study (DOI:10.1016/j.jmb.2008.01.031).)

Mechanism summary

Mode of action: CELL_WALL_SYNTHESIS_INHIBITION microbial target — CURATOR: whole-cell solid-state NMR in PMID:18258256 showed that oritavancin binds Staphylococcus aureus peptidoglycan through the D-Ala-D-Ala stem terminus and pentaglycyl bridge. The same study measured inhibition of both transglycosylation and transpeptidation, supporting a dual cell-wall-biosynthesis mechanism.

Record-level evidence

PMID:18258256 (Primary compound-specific dual cell-wall mechanism study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, antibacterial class, and roles; added the dual cell-wall-synthesis mechanism and primary NMR support beside the two preserved CARD cell-wall assertions.
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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