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

• ChemBase ID: 176791
• Molecular Formular: C17H32Cl2N2O5S
• Molecular Mass: 447.41738
• Monoisotopic Mass: 446.14089849
• SMILES: [C@@H]([C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)SC)O)O)O)([C@@H](C)Cl)NC(=O)[C@H]1NCC[C@H](C1)CC.Cl
• Canonical SMILES: CC[C@@H]1CCN[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](Cl)C.Cl
• InChI: InChI=1S/C17H31ClN2O5S.ClH/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3;/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24);1H/t8?,9-,10+,11?,12+,13-,14-,15-,17-;/m1./s1
• InChIKey: DPVJWUUBZWFDPG-DBZVBQDQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-4-ethylpiperidine-2-carboxamide hydrochloride
• IUPAC Traditional name: pirlimycin hydrochloride
• Synonyms: (2S-cis)-Methyl 7-Chloro-6,7,8-trideoxy-6-[[(4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-L-threo-α-D-galactoοctopyranoside Hydrochloride; Pirsue; U 57930E; Pirlimycin Hydrochloride

Database IDs

• CAS Number: 78822-40-9
• PubChem SID: 164232701
• PubChem CID: 71751697

CALCULATED PROPERTIES

• Acid pKa: 12.142037
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.4278677
• LogD (pH = 7.4): -0.9097703
• Log P: 0.576736
• Molar Refractivity: 100.4996 cm^3
• Polarizability: 40.877544 Å^3
• Polar Surface Area: 111.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: >198°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P509300

Semi-synthetic lincosaminide antibiotic; structural analog of Clindamycin. Antibacterial.

REFERENCES

• Ahonkhai, V.I., et al.: Antimicrob. Agents Chemother., 21, 902 (1982)
• Qadri, S.M.H., et al.: J. Antibiot., 36, 42 (1982)
• Birkenmeyer, R.D., et al.: J. Med. Chem., 27, 216 (1982)