CHEBI:4309 - dalfopristin

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ChEBI Name dalfopristin
ChEBI ID CHEBI:4309
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42127
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Formula C34H50N4O9S
Net Charge 0
Average Mass 690.850
Monoisotopic Mass 690.32985
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
InChIKey SUYRLXYYZQTJHF-VMBLUXKRSA-N
SMILES [H][C@]12[C@@H](CCN1C(=O)C1=COC(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@H](OC2=O)C(C)C)=N1)S(=O)(=O)CCN(CC)CC
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.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dalfopristin (CHEBI:4309) has functional parent pristinamycin IIA (CHEBI:9997)
dalfopristin (CHEBI:4309) has role antibacterial drug (CHEBI:36047)
dalfopristin (CHEBI:4309) has role protein synthesis inhibitor (CHEBI:48001)
dalfopristin (CHEBI:4309) is a 1,3-oxazoles (CHEBI:46812)
dalfopristin (CHEBI:4309) is a carboxylic ester (CHEBI:33308)
dalfopristin (CHEBI:4309) is a cyclic ketone (CHEBI:3992)
dalfopristin (CHEBI:4309) is a enamide (CHEBI:51751)
dalfopristin (CHEBI:4309) is a macrolide (CHEBI:25106)
dalfopristin (CHEBI:4309) is a macrolide antibiotic (CHEBI:25105)
dalfopristin (CHEBI:4309) is a secondary alcohol (CHEBI:35681)
dalfopristin (CHEBI:4309) is a secondary carboxamide (CHEBI:140325)
dalfopristin (CHEBI:4309) is a sulfone (CHEBI:35850)
dalfopristin (CHEBI:4309) is a tertiary amino compound (CHEBI:50996)
dalfopristin (CHEBI:4309) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name
(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
INNs Sources
dalfopristin WHO MedNet
dalfopristina WHO MedNet
dalfopristine WHO MedNet
dalfopristinum WHO MedNet
Synonyms Sources
RP 54476 ChemIDplus
RP-54476 DrugCentral
RP54476 ChEBI
Manual Xrefs Databases
778 DrugCentral
C08033 KEGG COMPOUND
D00853 KEGG DRUG
Dalfopristin Wikipedia
DB01764 DrugBank
DOL PDBeChem
HMDB0015566 HMDB
View more database links
Registry Number Type Source
112362-50-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
02 October 2020