(4R,5S,6S)-3-{[(3S,5S)-5-[(3S)-3-(2-carbamimidamidoacetamido)pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

• ChemBase ID: 178740
• Molecular Formular: C23H35N7O6S
• Molecular Mass: 537.6323
• Monoisotopic Mass: 537.23695288
• SMILES: [C@@H]12N(C(=C([C@@H]1C)S[C@@H]1CN([C@@H](C1)C(=O)N1CC[C@@H](C1)NC(=O)CNC(=N)N)C)C(=O)O)C(=O)[C@@H]2[C@H](O)C
• Canonical SMILES: NC(=N)NCC(=O)N[C@H]1CCN(C1)C(=O)[C@@H]1C[C@@H](CN1C)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@H](C2=O)[C@H](O)C
• InChI: InChI=1S/C23H35N7O6S/c1-10-17-16(11(2)31)21(34)30(17)18(22(35)36)19(10)37-13-6-14(28(3)9-13)20(33)29-5-4-12(8-29)27-15(32)7-26-23(24)25/h10-14,16-17,31H,4-9H2,1-3H3,(H,27,32)(H,35,36)(H4,24,25,26)/t10-,11-,12+,13+,14+,16-,17-/m1/s1
• InChIKey: KEDAXBWZURNCHS-GPODMPQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S)-3-{[(3S,5S)-5-[(3S)-3-(2-carbamimidamidoacetamido)pyrrolidine-1-carbonyl]-1-methylpyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• IUPAC Traditional name: tomopenem
• Synonyms: (4R,5S,6S)-3-[[(3S,5S)-5-[[(3S)-3-[[2-[(Aminoiminomethyl)amino]acetyl]amino]-1-pyrrolidinyl]carbonyl]-1-methyl-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid; Antibiotic CS 023; CS 023; R 115685; R 1558; Ro 4908463; Tomopenem

Database IDs

• CAS Number: 222400-20-6
• PubChem SID: 164234650
• PubChem CID: 9809656

CALCULATED PROPERTIES

• Acid pKa: 3.5232494
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -7.700236
• LogD (pH = 7.4): -5.968583
• Log P: -5.4597354
• Molar Refractivity: 147.2154 cm^3
• Polarizability: 52.491436 Å^3
• Polar Surface Area: 192.39 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T538550

Carbapenem Antibiotic.

REFERENCES

• Shahid, M., et al.: Crit. Rev. Microbiol., 35, 81 (2009)
• Varma, M., et al.: J. Med. Chem., 52, 4844 (2009)
• Mallalieu, N., et al.: Brit. J. Clin. Pharmacol., 67, 469 (2009)