4-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-benzenesulfonic acid 4-(2-nitro-vinyl)-phenyl ester

ID: ALA418906

Chembl Id: CHEMBL418906

PubChem CID: 14862539

Max Phase: Preclinical

Molecular Formula: C22H25N3O8S

Molecular Weight: 491.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NCCNC(=O)c1ccc(S(=O)(=O)Oc2ccc(/C=C/[N+](=O)[O-])cc2)cc1

Standard InChI:  InChI=1S/C22H25N3O8S/c1-22(2,3)32-21(27)24-14-13-23-20(26)17-6-10-19(11-7-17)34(30,31)33-18-8-4-16(5-9-18)12-15-25(28)29/h4-12,15H,13-14H2,1-3H3,(H,23,26)(H,24,27)/b15-12+

Standard InChI Key:  BHQGHWWROTWESK-NTCAYCPXSA-N

Alternative Forms

1. Parent:

   

   ALA418906

   4-(2-Nitrovinyl)phenyl 4-(2-(tert-butoxycarbonylamino)ethylcarbamoyl)benzenesulfonate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.52

Molecular Weight (Monoisotopic): 491.1362

AlogP: 2.96

#Rotatable Bonds: 9

Polar Surface Area: 153.94

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.55

CX Basic pKa: ┄

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.23

Np Likeness Score: -0.73

References

1. Traxler PM, Wacker O, Bach HL, Geissler JF, Kump W, Meyer T, Regenass U, Roesel JL, Lydon N..  (1991)  Sulfonylbenzoyl-nitrostyrenes: potential bisubstrate type inhibitors of the EGF-receptor tyrosine protein kinase.,  34  (8): [PMID:1652014] [10.1021/jm00112a003]

2. Chang CJ, Geahlen RL..  (1992)  Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.,  55  (11): [PMID:1479375] [10.1021/np50089a001]

Source

Source(1):

• Scientific Literature