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CHEBI:4309 - dalfopristin

ChEBI IDCHEBI:4309
ChEBI Namedalfopristin
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:42127
Last Modified2 October 2020
DownloadsMolfile
FormulaC34H50N4O9S
Net Charge0
Average Mass690.860
Monoisotopic Mass690.32985
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
InChIInChI=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
InChIKeySUYRLXYYZQTJHF-VMBLUXKRSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
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  Source
dalfopristinWHO MedNet
dalfopristinaWHO MedNet
dalfopristinumWHO MedNet
dalfopristineWHO MedNet
Synonyms  Source
RP-54476DrugCentral
RP54476ChEBI
RP 54476ChemIDplus
Manual XrefsDatabases
C08033KEGG COMPOUND
D00853KEGG DRUG
DOLPDBeChem
778DrugCentral
DB01764DrugBank
HMDB0015566HMDB
DalfopristinWikipedia
Registry NumbersSources
CAS:112362-50-2ChemIDplus
Citations