Retapamulin - Moligand™, ≥99% , 70S ribosome inhibitor, CAS No.224452-66-8, 70S ribosome inhibitor

CAS: 224452-66-8 Cat. No.: R125875 Molecular Weight: 517.76 EC Number: 639-491-7 PubChem CID: 6918462

GRADE & PURITY Moligand™, ≥99%

Synonyms

DTXSID30181492 | HY-17010 | Altargo | RETAPAMULIN [MI] | RETAPAMULIN [INN] | (3aS,4R,5S,6S,8R,9R,9aR,10R)-2-(exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ylsulfanyl)acetic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinylperhydro-3a,9-propanocyclopentacyclooct

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Retapamulin is a topical antibiotic, which binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM.
A broad spectrum antibiotic with no cross resistance to existing classes

Specifications

Synonyms

DTXSID30181492 | HY-17010 | Altargo | RETAPAMULIN [MI] | RETAPAMULIN [INN] | (3aS, 4R, 5S, 6S, 8R, 9R, 9aR, 10R)-2-(exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ylsulfanyl)acetic acid 5-hydroxy-4, 6, 9, 10-tetramethyl-1-oxo-6-vinylperhydro-3a, 9-propanocyclopentacyclooct

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Retapamulin(SB-275833) is a topical antibiotic developed by GlaxoSmithKline. Retapamulin(SB-275833) is the first drug in the new class of pleuromutilin antibiotics to be approved for human use.Retapamulin(SB-275833) is marketed as an ointment under the br

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

70S ribosome inhibitor

Purity

≥99%

Product Properties

• ALogP: 6.1

Names and Identifiers

• Pubchem Sid: 504764371
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764371
• Canonical Smiles: CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
• IUPAC Name: [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
• InChIKey: STZYTFJPGGDRJD-FJJJPKKESA-N
• INCHI: 1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22?,24-,26+,27+,28-,29+,30+/m1/s1
• Isomeric SMILES: C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CSC4C[C@H]5CC[C@@H](C4)N5C)C
• PubChem CID: 6918462
• Molecular Weight: 517.76

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids
        • Level5 Mutilane diterpenoids
          • Level6 Mutilin derivatives
            • Level7 Pleuromutilin and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Mutilane diterpenoids - Mutilin derivatives
• Direct Parent: Pleuromutilin and derivatives
• Alternative Parents: Tropane alkaloids Piperidines N-alkylpyrrolidines Trialkylamines Secondary alcohols Ketones Carboxylic acid esters Amino acids and derivatives Sulfenyl compounds Monocarboxylic acids and derivatives Dialkylthioethers Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Pleuromutilin - Tropane alkaloid - Piperidine - N-alkylpyrrolidine - Pyrrolidine - Amino acid or derivatives - Carboxylic acid ester - Ketone - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid derivative - Thioether - Azacycle - Organoheterocyclic compound - Dialkylthioether - Sulfenyl compound - Monocarboxylic acid or derivatives - Carbonyl group - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.
• 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(Human)

Caco-2 (12174 Activities)

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HEK293 (82097 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Streptococcus pneumoniae (31063 Activities)

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Enterococcus (1748 Activities)

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Streptococcus viridans (303 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Staphylococcus (1598 Activities)

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Streptococcus agalactiae (1777 Activities)

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Streptococcus pyogenes (16140 Activities)

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Enterococcus faecium (13803 Activities)

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Bacillus subtilis (32866 Activities)

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Enterococcus faecalis (29875 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 104 mg/mL ;Water <1 mg/mL;Ethanol 104 mg/mL
• Molecular Weight: 517.799 g/mol
• XLogP3: 6.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 517.323 Da
• Monoisotopic Mass: 517.323 Da
• Topological Polar Surface Area: 92.100 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 895.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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