Quinupristin - Moligand™, ≥97% , Bacterial 70S ribosome inhibitor, CAS No.120138-50-3, Bacterial 70S ribosome inhibitor

CAS: 120138-50-3 Cat. No.: Q344294 Molecular Weight: 1022.2 PubChem CID: 5388937

GRADE & PURITY Moligand™, ≥97%

Synonyms

QUINUPRISTIN [MI] | Quinupristina | HY-A0162 | QUINUPRISTIN [USAN] | HSDB 8067 | QUINUPRISTIN [INN] | N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Quinupristin is a semi-synthetic analogue of virginiamycin B (ostreogyrcin B, pristinamycin IA, Streptogramin B) formed by a Mannich condensation and elimination to generate an exocyclic methylene alpha to the ketone of the 4-piperidinone. Addition of quinucidinylthiol to the methylene group affords quinupristin. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Quinupristin is used commercially in synergistic combination with dalfopristin (30:70). There is little published data on the synthesis, biological or antibiotic activity of quinupristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.

Specifications

Synonyms

QUINUPRISTIN [MI] | Quinupristina | HY-A0162 | QUINUPRISTIN [USAN] | HSDB 8067 | QUINUPRISTIN [INN] | N-[(3S, 6S, 12R, 15S, 16R, 19S, 22S, 25R)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylsulfanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4, 16-dimethyl-2, 5

Specifications & Purity

Moligand™, ≥97%

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

≥97%

Product Properties

• ALogP: 4.2

Names and Identifiers

• Pubchem Sid: 504763815
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763815
• Canonical Smiles: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CC(C(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CSC6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
• IUPAC Name: N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]sulfanylmethyl]-3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
• InChIKey: WTHRRGMBUAHGNI-LCYNINFDSA-N
• INCHI: 1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1
• Isomeric SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
• PubChem CID: 5388937
• Molecular Weight: 1022.2

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Depsipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Depsipeptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic depsipeptides
• Alternative Parents: Macrolide lactams Alpha amino acid esters Macrolactams N-acyl-alpha amino acids and derivatives Pyridinecarboxamides Quinuclidines 2-heteroaryl carboxamides Aniline and substituted anilines Dialkylarylamines Piperidinones Hydroxypyridines Pyrrolidines Vinylogous acids Heteroaromatic compounds Tertiary carboxylic acid amides Secondary carboxylic acid amides Carboxylic acid esters Cyclic ketones Lactams Lactones Trialkylamines Dialkylthioethers Sulfenyl compounds Monocarboxylic acids and derivatives Azacyclic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cyclic depsipeptide - Macrolide lactam - N-acyl-alpha amino acid or derivatives - Alpha-amino acid ester - Macrolactam - Alpha-amino acid or derivatives - Pyridine carboxylic acid or derivatives - Pyridinecarboxamide - 2-heteroaryl carboxamide - Aniline or substituted anilines - Dialkylarylamine - Quinuclidine - Tertiary aliphatic/aromatic amine - Piperidinone - Hydroxypyridine - Monocyclic benzene moiety - Piperidine - Benzenoid - Pyridine - Vinylogous acid - Pyrrolidine - Tertiary carboxylic acid amide - Heteroaromatic compound - Amino acid or derivatives - Carboxamide group - Carboxylic acid ester - Ketone - Lactam - Lactone - Cyclic ketone - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxylic acid derivative - Azacycle - Monocarboxylic acid or derivatives - Oxacycle - Thioether - Sulfenyl compound - Dialkylthioether - Organoheterocyclic compound - Amine - Organic oxide - Organooxygen compound - Organosulfur compound - Organic nitrogen compound - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
• 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

Mycolicibacterium smegmatis (8003 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: Soluble in alcohol, water (slightly), and DMSO.
• Refractive Index: n20D1.66
• Molecular Weight: 1022.200 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 10
• Exact Mass: 1021.47 Da
• Monoisotopic Mass: 1021.47 Da
• Topological Polar Surface Area: 257.000 Ų
• Heavy Atom Count: 73
• Formal Charge: 0
• Complexity: 2010.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1