(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

• ChemBase ID: 132521
• Molecular Formular: C18H35ClN2O6S
• Molecular Mass: 442.9983
• Monoisotopic Mass: 442.19043553
• SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)SC)O)O)O)[C@@H](C)O.Cl
• Canonical SMILES: CCC[C@H]1CN([C@@H](C1)C(=O)N[C@@H]([C@H]1O[C@H](SC)[C@@H]([C@H]([C@H]1O)O)O)[C@H](O)C)C.Cl
• InChI: InChI=1S/C18H34N2O6S.ClH/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1
• InChIKey: POUMFISTNHIPTI-BOMBIWCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• IUPAC Traditional name: lincomycin hydrochloride
• Synonyms: Lincomycin hydrochloride; Lincocin hydrochloride; Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galactooctopyranoside hydrochloride; Lincocin 盐酸盐; Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galactooctopyranoside 盐酸盐; Lincomycin hydrochloride 盐酸盐

Database IDs

• CAS Number: 859-18-7
• EC Number: 212-726-7
• MDL Number: MFCD00083647
• Beilstein Number: 4171650
• PubChem SID: 162226798
• PubChem CID: 64710

CALCULATED PROPERTIES

• Acid pKa: 12.365502
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.7498562
• LogD (pH = 7.4): -0.99001026
• Log P: -0.3168542
• Molar Refractivity: 102.6663 cm^3
• Polarizability: 41.491238 Å^3
• Polar Surface Area: 122.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• RTECS: RH6315000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (TLC); ≥95.0% (TLC)
• Potency: 800-900 units per mg
• Suitability: suitable for cell culture
• Impurities: ≤5% water
• Empirical Formula (Hill Notation): C18H34N2O6S · HCl

DETAILS

Sigma Aldrich - L2774

Biochem/physiol Actions
Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA.1Mode of action: inhibits bacterial protein synthesis Antimicrobial spectrum: Gram-positive bacteria
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - L6004

Biochem/physiol Actions
Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA.3Mode of action: inhibits bacterial protein synthesis Antimicrobial spectrum: Gram-positive bacteria
Application
Lincomycin hydrochloride is an antibiotic used to study the inhibition of protein synthesis, bacterial antibiotic resistance, and protein and surfactant binding 1,2 Product L6004 is ≥90% (TLC). It is produced by Streptomyces lincolnensis var. lincolnensis and has been used in the treatment of Staphylococcal, Streptococcal, and Bacteroides fragilis infections.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 62143

Biochem/physiol Actions
Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA.3Mode of action: inhibits bacterial protein synthesis Antimicrobial spectrum: Gram-positive bacteria
Other Notes
Review4
Application
Lincomycin hydrochloride is used to study the inhibition of protein synthesis, bacterial antibiotic resistance, and protein and surfactant binding 1,2