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dalfopristin   Click here for help

GtoPdb Ligand ID: 10797

Synonyms: RP-54476 | RP54476 | Synercid® (dalfopristin + quinupristin)
Approved drug PDB Ligand
dalfopristin is an approved drug (FDA (1999))
Compound class: Synthetic organic
Comment: Dalfopristin is a semi-synthetic derivative of pristinamycin IIA (streptogramin A). It inhibits the early phase of protein synthesis in the bacterial ribosome by binding to the 70S subunit. It is administered intravenously.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 184.8
Molecular weight 690.33
XLogP 1.7
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCN(CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc1nc(C2=O)co1)O)/C)CC
Isomeric SMILES CCN(CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc1nc(C2=O)co1)O)/C)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
InChI Key SUYRLXYYZQTJHF-VMBLUXKRSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1999)
IUPAC Name Click here for help
(6R,7S,10R,11R,12E,17E,19E,21S)-6-[2-(diethylamino)ethylsulfonyl]-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetrone
International Nonproprietary Names Click here for help
INN number INN
6581 dalfopristin
Synonyms Click here for help
RP-54476 | RP54476 | Synercid® (dalfopristin + quinupristin)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Dalfopristin | Quinupristin/dalfopristin (Synercid)
Other databases
CAS Registry No. 112362-50-2 (source: WHO INN record)
GtoPdb PubChem SID 405560238
PubChem CID 6323289
RCSB PDB Ligand DOL
Search Google for chemical match using the InChIKey SUYRLXYYZQTJHF-VMBLUXKRSA-N
Search Google for chemicals with the same backbone SUYRLXYYZQTJHF
Search PubMed clinical trials dalfopristin
Search PubMed titles dalfopristin
Search PubMed titles/abstracts dalfopristin
UniChem Compound Search for chemical match using the InChIKey SUYRLXYYZQTJHF-VMBLUXKRSA-N
UniChem Connectivity Search for chemical match using the InChIKey SUYRLXYYZQTJHF-VMBLUXKRSA-N