Dalfopristin - Moligand™, ≥98%, mixture of isomers , Bacterial 70S ribosome inhibitor, CAS No.112362-50-2, Bacterial 70S ribosome inhibitor

CAS: 112362-50-2 Cat. No.: D329279 Molecular Weight: 690.85

GRADE & PURITY Moligand™, ≥98%, mixture of isomers

Synonyms

(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 | DALFOPRISTIN [INN] | DALFOPRISTIN [WHO-DD]

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Dalfopristin is a semi-synthetic analogue of ostreogyrcin A (virginiamycin M, pristinamycin IIA, streptogramin A) formed by addition of diethylaminoethylthiol to the 2-pyrroline group of ostreogyrcin, followed by oxidation to the sulphone. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Dalfopristin is used commercially in synergistic combination with quinupristin (70:30). There is little published data on the synthesis, biological or antibiotic activity of dalfopristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.

Specifications

Synonyms

(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 | DALFOPRISTIN [INN] | DALFOPRISTIN [WHO-DD]

Specifications & Purity

Moligand™, ≥98%, mixture of isomers

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Bacterial 70S ribosome inhibitor

Purity

≥98%

Product Properties

• pKa: pKₐ: 13.18 (Predicted), pKₐ: 8.97 (Predicted)
• ALogP: 2.2

Names and Identifiers

• Pubchem Sid: 504764033
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764033
• Canonical Smiles: CCN(CC)CCS(=O)(=O)C1CCN2C1C(=O)OC(C(C=CC(=O)NCC=CC(=CC(CC(=O)CC3=NC(=CO3)C2=O)O)C)C)C(C)C
• IUPAC Name: (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
• InChIKey: SUYRLXYYZQTJHF-VMBLUXKRSA-N
• 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
• Isomeric SMILES: CCN(CC)CCS(=O)(=O)[C@@H]1CCN2[C@H]1C(=O)O[C@@H]([C@@H](/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)CC3=NC(=CO3)C2=O)O)/C)C)C(C)C
• WGK Germany: 3
• Molecular Weight: 690.85
• Reaxy-Rn: 37816240
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37816240&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolide lactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolide lactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolide lactams
• Alternative Parents: Alpha amino acid esters Macrolactams 2-heteroaryl carboxamides Tertiary carboxylic acid amides Heteroaromatic compounds Sulfones Oxazoles Pyrrolidines Lactones Lactams Trialkylamines Carboxylic acid esters Cyclic ketones Secondary alcohols Secondary carboxylic acid amides Monocarboxylic acids and derivatives Azacyclic compounds Oxacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Macrolide lactam - Alpha-amino acid ester - Macrolactam - Alpha-amino acid or derivatives - 2-heteroaryl carboxamide - Azole - Heteroaromatic compound - Oxazole - Pyrrolidine - Sulfone - Sulfonyl - Tertiary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Carboxylic acid ester - Ketone - Lactam - Lactone - Secondary alcohol - Secondary carboxylic acid amide - Cyclic ketone - Tertiary amine - Tertiary aliphatic amine - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxygen compound - Amine - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Alcohol - Organopnictogen compound - Carbonyl group - Organic oxide - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (144.75）；Ethanol：100 mg/mL (144.75）；not soluble in water
• Refractive Index: n20D1.58
• Boil Point(°C): 940.5° C at 760 mmHg
• Molecular Weight: 690.800 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 690.33 Da
• Monoisotopic Mass: 690.33 Da
• Topological Polar Surface Area: 185.000 Ų
• Heavy Atom Count: 48
• Formal Charge: 0
• Complexity: 1340.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 3
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 3
• Covalently-Bonded Unit Count: 1