4-Butylcarbamoyl-benzenesulfonic acid 4-(2-nitro-vinyl)-phenyl ester

ID: ALA77100

Chembl Id: CHEMBL77100

PubChem CID: 14862537

Max Phase: Preclinical

Molecular Formula: C19H20N2O6S

Molecular Weight: 404.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H20N2O6S/c1-2-3-13-20-19(22)16-6-10-18(11-7-16)28(25,26)27-17-8-4-15(5-9-17)12-14-21(23)24/h4-12,14H,2-3,13H2,1H3,(H,20,22)/b14-12+

Standard InChI Key:  IYYHYDARBKIAKE-WYMLVPIESA-N

Alternative Forms

1. Parent:

   

   ALA77100

   4-(2-Nitrovinyl)phenyl 4-(butylcarbamoyl)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: 404.44

Molecular Weight (Monoisotopic): 404.1042

AlogP: 3.23

#Rotatable Bonds: 9

Polar Surface Area: 115.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.77

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.71

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