2-Acetylamino-3-{4-[4-(2-acetylamino-2-carboxy-ethylsulfanylcarbonylamino)-benzyl]-phenylcarbamoylsulfanyl}-propionic acid

ID: ALA190205

Chembl Id: CHEMBL190205

PubChem CID: 44398873

Max Phase: Preclinical

Molecular Formula: C25H28N4O8S2

Molecular Weight: 576.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC(CSC(=O)Nc1ccc(Cc2ccc(NC(=O)SCC(NC(C)=O)C(=O)O)cc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C25H28N4O8S2/c1-14(30)26-20(22(32)33)12-38-24(36)28-18-7-3-16(4-8-18)11-17-5-9-19(10-6-17)29-25(37)39-13-21(23(34)35)27-15(2)31/h3-10,20-21H,11-13H2,1-2H3,(H,26,30)(H,27,31)(H,28,36)(H,29,37)(H,32,33)(H,34,35)

Standard InChI Key:  WVYBIYOMZGTTMD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA190205

   2-Acetylamino-3-{4-[4-(2-acetylamino-2-carboxy-ethylsulfanylcarbonylamino)-benzyl]-phenylcarbamoylsulfanyl}-propionic acid

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: 576.65

Molecular Weight (Monoisotopic): 576.1349

AlogP: 2.99

#Rotatable Bonds: 12

Polar Surface Area: 191.00

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.19

CX Basic pKa: ┄

CX LogP: 2.19

CX LogD: -4.56

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.22

Np Likeness Score: -0.16

References

1. Seefeldt T, Dwivedi C, Peitz G, Herman J, Carlson L, Zhang Z, Guan X..  (2005)  2-Acetylamino-3-[4-(2-acetylamino-2-carboxyethylsulfanylcarbonylamino)- phenylcarbamoylsulfanyl]propionic acid and its derivatives as a novel class of glutathione reductase inhibitors.,  48  (16): [PMID:16078841] [10.1021/jm050030i]

Source

Source(1):

• Scientific Literature