(2E)-2-[(3-butanamido-2,4,6-triiodophenyl)methylidene]butanoic acid

• ChemBase ID: 4358
• Molecular Formular: C15H16I3NO3
• Molecular Mass: 639.00585
• Monoisotopic Mass: 638.82643738
• SMILES: Ic1c(NC(=O)CCC)c(I)cc(I)c1/C=C(\CC)/C(=O)O
• Canonical SMILES: CCCC(=O)Nc1c(I)cc(c(c1I)/C=C(/C(=O)O)\CC)I
• InChI: InChI=1S/C15H16I3NO3/c1-3-5-12(20)19-14-11(17)7-10(16)9(13(14)18)6-8(4-2)15(21)22/h6-7H,3-5H2,1-2H3,(H,19,20)(H,21,22)/b8-6+
• InChIKey: CWRBDUIQDIHWJZ-SOFGYWHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-[(3-butanamido-2,4,6-triiodophenyl)methylidene]butanoic acid
• IUPAC Traditional name: bunamiodyl
• Brand Name: Bunamijodylum; Buniodyl
• Synonyms: 2-(3-Butyramido-3,4,6-triiodophenylmethylene)butyric acid; 3-(3-Butylamido-2,4,6-triiodphenyl)-2-ethylacrylsaeure; Bunamiodilo [inn-spanish]; Bunamiodylum [inn-latin]; Bunamiodyl

Database IDs

• CAS Number: 1233-53-0
• PubChem SID: 160967790; 46504825
• PubChem CID: 6436657

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.3722718
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.1628475
• LogD (pH = 7.4): 2.6299486
• Log P: 6.1458535
• Molar Refractivity: 116.1964 cm^3
• Polarizability: 44.46173 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.1
• LOG S: -5.44
• Solubility (Water): 2.30e-03 g/l

DETAILS

DrugBank - DB04814

• Drug Groups: withdrawn
• Description: Withdrawn from the Canadian, US, and UK markets in 1963 due to nephropathy.