dalfopristin

CHEBI:4309 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A macrolide that is pristinamycin IIA in which the double bond between positions 26 and 26a of the pyrroline ring has been reduced and position 26R carries a [2-(diethylamino)ethyl]sulfonyl group. It is a semi-synthetic streptogramin antibiotic and often used as a mixture with quinupristin for the treatment of vancomycin-resistant Enterococcus faecium. — 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

streptogramin antibioticARO:0000026

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140325 CHEBI:140325
CHEBI:140326 CHEBI:140326
CHEBI:25105 CHEBI:25105
CHEBI:25106 CHEBI:25106
CHEBI:33308 CHEBI:33308
CHEBI:35681 CHEBI:35681
CHEBI:35850 CHEBI:35850
CHEBI:3992 CHEBI:3992
CHEBI:46812 CHEBI:46812
CHEBI:50996 CHEBI:50996
CHEBI:51751 CHEBI:51751
ARO:0000026 ARO:0000026

Chemical structure

Computed structure properties
Molecular formula	C34H50N4O9S
Charge	0
Average mass	690.86 Da
Monoisotopic mass	690.32985 Da
Source	ChEBI
InChIKey	SUYRLXYYZQTJHF-VMBLUXKRSA-N

SMILES

[H][C@@]12C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(C)=C/[C@@H](O)CC(=O)Cc3nc(co3)C(=O)N1CC[C@H]2S(=O)(=O)CCN(CC)CC

InChI

InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1

Also called

dalfopristina (INN)— chebi
dalfopristine (INN)— chebi
dalfopristinum (INN)— chebi
(3R,4R,5E,10E,12E,14S,26R,26aS)-26-{[2-(diethylamino)ethyl]sulfonyl}-14-hydroxy-4,12-dimethyl-3-(propan-2-yl)-8,9,14,15,24,25,26,26a-octahydro-1H,3H,22H-21,18-(azeno)pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone (EXACT_SYNONYM)— chebi
RP 54476 (EXACT_SYNONYM)— chebi
RP-54476 (EXACT_SYNONYM)— chebi
RP54476 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000674
cas:112362-50-2
drugbank:DB01764
drugcentral:778
hmdb:HMDB0015566
kegg.compound:C08033
kegg.drug:D00853
pdb-ccd:DOL
wikipedia.en:Dalfopristin
chembl:CHEMBL1200937
pubchem.compound:6323289

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:3000674`	dalfopristin	`antibioticmech:aro-204bbf1b11`	2026-08-30
CHEBI	`CHEBI:4309`	dalfopristin	`antibioticmech:chebi-73c4cfe8cd`	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.

antibiotic sensitive peptidyl transferase (23S rRNA) NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000754

CARD/ARO database assertion; target organism, strain, and assay are not specified. 23S rRNA peptidyl-transferase center is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000754 (CARD/ARO asserts targeted_by_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Resistance mechanisms

30 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 25

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Erm(33)	ARO:3000599	not organism-specific	—	ARO:3000599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(34)	ARO:3000600	not organism-specific	—	ARO:3000600 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(35)	ARO:3000604	not organism-specific	—	ARO:3000604 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(36)	ARO:3000605	not organism-specific	—	ARO:3000605 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(37)	ARO:3000392	not organism-specific	—	ARO:3000392 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(38)	ARO:3000601	not organism-specific	—	ARO:3000601 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(39)	ARO:3000602	not organism-specific	—	ARO:3000602 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
Erm(41)	ARO:3000603	not organism-specific	—	ARO:3000603 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmA	ARO:3000347	not organism-specific	—	ARO:3000347 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmB	ARO:3000375	not organism-specific	—	ARO:3000375 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmC	ARO:3000250	not organism-specific	—	ARO:3000250 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmD	ARO:3000495	not organism-specific	—	ARO:3000495 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmE	ARO:3000326	not organism-specific	—	ARO:3000326 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmF	ARO:3000498	not organism-specific	—	ARO:3000498 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmG	ARO:3000522	not organism-specific	—	ARO:3000522 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmN	ARO:3000592	not organism-specific	—	ARO:3000592 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmQ	ARO:3000593	not organism-specific	—	ARO:3000593 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmR	ARO:3000594	not organism-specific	—	ARO:3000594 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmT	ARO:3000595	not organism-specific	—	ARO:3000595 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
ErmX	ARO:3000596	not organism-specific	—	ARO:3000596 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
cfrA	ARO:3003441	not organism-specific	—	ARO:3003441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
cipA	ARO:3003907	not organism-specific	—	ARO:3003907 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
clbA	ARO:3002814	not organism-specific	—	ARO:3002814 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
clbB	ARO:3002815	not organism-specific	—	ARO:3002815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
clbC	ARO:3002816	not organism-specific	—	ARO:3002816 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 3

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
lsaA	ARO:3000300	not organism-specific	—	ARO:3000300 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
vgaB	ARO:3000118	not organism-specific	—	ARO:3000118 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)
vgaD	ARO:3002832	not organism-specific	—	ARO:3002832 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
lmrP	ARO:3003969	not organism-specific	—	ARO:3003969 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

ANTIBIOTIC_INACTIVATION 1

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
streptogramin vat acetyltransferase	ARO:3000453	not organism-specific	—	ARO:3000453 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

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

Provenance

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