(1s,4s)-4-{1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentaneamido}cyclohexane-1-carboxylic acid

• ChemBase ID: 163574
• Molecular Formular: C29H41NO7
• Molecular Mass: 515.63834
• Monoisotopic Mass: 515.28830266
• SMILES: C1CC(CC1)(C[C@H](C(=O)Oc1ccc2c(c1)CCC2)COCCOC)C(=O)N[C@H]1CC[C@H](CC1)C(=O)O
• Canonical SMILES: COCCOC[C@@H](C(=O)Oc1ccc2c(c1)CCC2)CC1(CCCC1)C(=O)N[C@@H]1CC[C@@H](CC1)C(=O)O
• InChI: InChI=1S/C29H41NO7/c1-35-15-16-36-19-23(27(33)37-25-12-9-20-5-4-6-22(20)17-25)18-29(13-2-3-14-29)28(34)30-24-10-7-21(8-11-24)26(31)32/h9,12,17,21,23-24H,2-8,10-11,13-16,18-19H2,1H3,(H,30,34)(H,31,32)/t21-,23-,24+/m0/s1
• InChIKey: ZTWZVMIYIIVABD-OEMFJLHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,4s)-4-{1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentaneamido}cyclohexane-1-carboxylic acid
• IUPAC Traditional name: candoxatril
• Synonyms: cis-4-[[[1-[(2S)-3-[(2,3-Dihydro-1H-inden-5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]cyclohexanecarboxylic Acid; UK 79300; Candoxatril

Database IDs

• CAS Number: 123122-55-4
• PubChem SID: 162257709
• PubChem CID: 5362417

CALCULATED PROPERTIES

• Acid pKa: 4.2854137
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.4405584
• LogD (pH = 7.4): 1.7053081
• Log P: 4.6791506
• Molar Refractivity: 138.1581 cm^3
• Polarizability: 54.23496 Å^3
• Polar Surface Area: 111.16 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C175200

Neutral endopeptidase inhibitor. Used in treatment of congestive heart failure.

REFERENCES

• Motwani, J.G., et al.: Clin. Pharmacol. Ther., 54, 661 (1993)
• Kimmelstiel, C.D., et al.: Cardiology, 87, 46 (1993)