iPPI-DB

Inhibitors of Protein-Protein Interaction Database

Compound 973

Identifiers

  • Canonical SMILES: 
    C[C@@H](N1[C@@H](c2ccc(Cl)cc2)C(=O)N(CCCCC(O)=O)c2ccc(I)cc2C1=O)c1ccc(Cl)cc1
  • IUPAC name: 
    5-[(3S)-3-(4-chlorophenyl)-4-[(1R)-1-(4-chlorophenyl)ethyl]-7-iodo-2,5-dioxo-3H-1,4-benzodiazepin-1-yl]pentanoic acid
  • InChi: 
    InChI=1S/C28H25Cl2IN2O4/c1-17(18-5-9-20(29)10-6-18)33-26(19-7-11-21(30)12-8-19)28(37)32(15-3-2-4-25(34)35)24-14-13-22(31)16-23(24)27(33)36/h5-14,16-17,26H,2-4,15H2,1H3,(H,34,35)/t17-,26+/m1/s1
  • InChiKey: 
    VLOPNYYNACVDTC-QUGAMOGWSA-N

External links


11952815
CHEMBL210151
23271977

External search

Bibliography (3)

Publication Name
Parks DJ, LaFrance LV, Calvo RR, Milkiewicz KL, Marugán JJ, Raboisson P, Schubert C, Koblish HK, Zhao S, Franks CF, Lattanze J, Carver TE, Cummings MD, Maguire D, Grasberger BL, Maroney AC, Lu T. . Enhanced pharmacokinetic properties of 1,4-benzodiazepine-2,5-dione antagonists of the HDM2-p53 protein-protein interaction through structure-based drug design. Bioorganic & medicinal chemistry letters. 19
Marugan JJ, Leonard K, Raboisson P, Gushue JM, Calvo R, Koblish HK, Lattanze J, Zhao S, Cummings MD, Player MR, Schubert C, Maroney AC, Lu T. . Enantiomerically pure 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists. Bioorganic & medicinal chemistry letters. 12b
Leonard K, Marugan JJ, Raboisson P, Calvo R, Gushue JM, Koblish HK, Lattanze J, Zhao S, Cummings MD, Player MR, Maroney AC, Lu T. . Novel 1,4-benzodiazepine-2,5-diones as Hdm2 antagonists with improved cellular activity. Bioorganic & medicinal chemistry letters. 1

Pharmacological data

Biochemical tests Cellular tests PK tests Cytotoxicity tests
3 2 0 0

Targets

PPI family Best activity Diseases MMoA
MDM2-Like / P53 6.15 cancer Inhibition
Physicochemical filters
Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 650.02 g/mol
HBA 6
HBD 1
HBA + HBD 7
AlogP 6.74
TPSA 77.92
RB 8
Radar chart
PCA : iPPI-DB chemical space
PCA : Correlation circle
Efficiencies: iPPI-DB biplot LE versus LLE
Summary
Bibliographic ressources Biochemical tests Cellular tests PK tests Cytotoxicity tests
3 3 2 0 0
Pharmacological data
Bibliography Name Target Competition Assay type Assay name Cell line Activity type Activity
16647257 1 MDM2
Q00987
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.07
16630722 12b MDM2
Q00987
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.07
16600594 19 MDM2
Q00987
Biochemical assay Fluorescence Polarization pIC50 (half maximal inhibitory concentration, -log10) 6.15
16600594 19 MDM2
Q00987
Cellular assay Proliferation assay MCF7 mammary carcinoma cells pIC50 (half maximal inhibitory concentration, -log10) 5.15
16600594 19 MDM2
Q00987
Cellular assay Proliferation assay MDA MB321 mammary carcinoma cells pIC50 (half maximal inhibitory concentration, -log10) 4.17
Ta Structure Name Drugbank ID
0.5454 4-[(4-bromo-2-{[(3R,5S)-3,5-dimethylpiperidin-1-yl]carbonyl}phenyl)amino]-4-oxobutanoic acid DB08581
0.5417 Bentiromide DB00522
0.5247 [(2S)-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-yl]acetic acid DB08717
0.5230 Delparantag DB12955
0.5226 4-chloro-N-(3-methoxypropyl)-N-[(3S)-1-(2-phenylethyl)piperidin-3-yl]benzamide DB08344
0.5198 Ombitasvir DB09296
0.5157 OPC-28326 DB05461
0.5153 Dexloxiglumide DB04856
0.5125 Balicatib DB12239
0.5026 Repaglinide DB00912
0.4974 CP-320626 DB03383
0.4972 N-(4-bromo-2-{[(3R,5S)-3,5-dimethylpiperidin-1-yl]carbonyl}phenyl)-4-morpholin-4-yl-4-oxobutanamide DB08582
0.4942 AGG-523 DB15460
0.4934 Proglumide DB13431
0.4917 2-{[4-(2-Acetylamino-2-pentylcarbamoyl-ethyl)-naphthalen-1-YL]-oxalyl-amino}-benzoic acid DB01820