cyclopentyl 2-[(2R,3S)-3-hydroxy-3-(hydroxycarbamoyl)-2-(2-methylpropyl)propanamido]-2-(2H5)phenylacetate

• ChemBase ID: 178753
• Molecular Formular: C21H30N2O6
• Molecular Mass: 406.4727
• Monoisotopic Mass: 406.21038669
• SMILES: C1CC(CC1)OC(=O)C(NC(=O)[C@H](CC(C)C)[C@@H](C(=O)NO)O)c1ccccc1
• Canonical SMILES: ONC(=O)[C@H]([C@H](C(=O)NC(c1ccccc1)C(=O)OC1CCCC1)CC(C)C)O
• InChI: InChI=1S/C21H30N2O6/c1-13(2)12-16(18(24)20(26)23-28)19(25)22-17(14-8-4-3-5-9-14)21(27)29-15-10-6-7-11-15/h3-5,8-9,13,15-18,24,28H,6-7,10-12H2,1-2H3,(H,22,25)(H,23,26)/t16-,17?,18+/m1/s1
• InChIKey: FWFGIHPGRQZWIW-BLAYRMRBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclopentyl 2-[(2R,3S)-3-hydroxy-3-(hydroxycarbamoyl)-2-(2-methylpropyl)propanamido]-2-(^2H₅)phenylacetate
• IUPAC Traditional name: cyclopentyl 2-[(2R,3S)-3-hydroxy-3-(hydroxycarbamoyl)-2-(2-methylpropyl)propanamido]-2-(^2H₅)phenylacetate
• Synonyms: (αS)-α-[[(2R)-2-[(1S)-1-Hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]amino]benzeneacetic Acid-d5 Cyclopentyl Ester; CHR 2797-d5; Tosedostat-d5

Database IDs

• PubChem SID: 164234663
• PubChem CID: 57369427

CALCULATED PROPERTIES

• Acid pKa: 8.610967
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.1267843
• LogD (pH = 7.4): 2.1013188
• Log P: 2.127119
• Molar Refractivity: 105.1308 cm^3
• Polarizability: 41.724995 Å^3
• Polar Surface Area: 124.96 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T549002

Labelled Tosedostat. CHR-2797 is a novel metalloenzyme inhibitor that is converted into a pharmacological active acid product (CHR-79888) inside cells. CHR-2797 exerts antiproliferative effects against a range of tumor cell lines in vitro and in vivo and

REFERENCES

• Sato, Y., et al.: Biol. Pharm. Bull., 27, 772 (2004)
• Saveanu, L., et al.: Nat. Immunol., 6, 689 (2004)
• Proud, C., et al.: Biochem. J., 403, 217 (2004)
• Watatani, Y., et al.: Life Sci., 80, 879 (2004)