(2Z)-7-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1R)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid

• ChemBase ID: 164756
• Molecular Formular: C16H26N2O5S
• Molecular Mass: 358.45304
• Monoisotopic Mass: 358.15624294
• SMILES: [C@@H]1(C(C1)(C)C)C(=O)N/C(=C\CCCCSC[C@H](C(=O)O)N)/C(=O)O
• Canonical SMILES: OC(=O)[C@@H](CSCCCC/C=C(/C(=O)O)\NC(=O)[C@@H]1CC1(C)C)N
• InChI: InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m0/s1
• InChIKey: DHSUYTOATWAVLW-RXOUDOFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-7-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1R)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid
• IUPAC Traditional name: (2Z)-7-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1R)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid
• Synonyms: (2Z)-7-[[(2R)-2-amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic Acid; MK-791; Cilastatin

Database IDs

• CAS Number: 82009-34-5
• PubChem SID: 162258891
• PubChem CID: 5311046

CALCULATED PROPERTIES

• Acid pKa: 2.5319705
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.295944
• LogD (pH = 7.4): -4.05599
• Log P: -1.259092
• Molar Refractivity: 92.8507 cm^3
• Polarizability: 36.12875 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Light-Yellow Solid
• Melting Point: 156-158°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C441100

Prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct.

REFERENCES

• Finlay, K.R., et al.: Invest. Ophthalmol. Visual Sci., 24, 1147 (1983)
• Norrby, S.R., et al.: Antimicrob. Agents Chemother., 23, 300 (1983)
• Washburn, D.E., et al.: J. Antimicrob. Chemother., 12, 39 (1983)