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

• ChemBase ID: 498
• Molecular Formular: C29H41NO7
• Molecular Mass: 515.63834
• Monoisotopic Mass: 515.28830266
• SMILES: O=C(NC1CCC(CC1)C(=O)O)C1(CCCC1)C[C@@H](COCCOC)C(=O)Oc1cc2c(CCC2)cc1
• Canonical SMILES: COCCOC[C@@H](C(=O)Oc1ccc2c(c1)CCC2)CC1(CCCC1)C(=O)NC1CCC(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-RZMWZJFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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: 4-{1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentaneamido}cyclohexane-1-carboxylic acid
• Brand Name: Candoxatrilat
• Synonyms: Candoxatril

Database IDs

• CAS Number: 118785-03-8
• PubChem SID: 160963961
• PubChem CID: 5362417

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.55
• LOG S: -5.36
• Solubility (Water): 2.25e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.7

DETAILS

DrugBank - DB00616

• Drug Groups: approved
• Description: Candoxatril is the orally-active prodrug of candoxatrilat (UK-73967), the active enantiomer of candoxatrilat (UK-69578), a potent neutral endopeptidase (NEP) inhibitor used in the treatment of chronic heart failure.
• Indication: For treatment of hypertension, improve exercise capacity in patients with CHF receiving angiotensin converting enzyme inhibition.
• Pharmacology: Candoxatril is the orally-active prodrug of candoxatrilat (UK-73967), the active enantiomer of candoxatrilat (UK-69578), a potent neutral endopeptidase (NEP) inhibitor used in the treatment of chronic heart failure in man.
• Affected Organisms: Humans and other mammals