2-mercapto-3-(2,3,6-trichlorophenyl)acrylic acid

ID: ALA3792857

Chembl Id: CHEMBL3792857

PubChem CID: 85470635

Max Phase: Preclinical

Molecular Formula: C9H5Cl3O2S

Molecular Weight: 283.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C(S)=C/c1c(Cl)ccc(Cl)c1Cl

Standard InChI:  InChI=1S/C9H5Cl3O2S/c10-5-1-2-6(11)8(12)4(5)3-7(15)9(13)14/h1-3,15H,(H,13,14)/b7-3-

Standard InChI Key:  ZCOCHUAGSBNGCP-CLTKARDFSA-N

Alternative Forms

1. Parent:

   

   ALA3792857

   (2z)-2-Sulfanyl-3-(2,3,6-Trichlorophenyl)prop-2-Enoic 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: 283.56

Molecular Weight (Monoisotopic): 281.9076

AlogP: 4.00

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.73

CX Basic pKa:

CX LogP: 3.94

CX LogD: 0.47

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.49

Np Likeness Score: -0.46

References

1. Betts JW, Phee LM, Abdul Momin MHF, Umland K, Brem J, Schofield CJ, Wareham DW.  (2016)  In vitro and in vivo activity of ML302F: a thioenolate inhibitor of VIM-subfamily metallo -lactamases,  7  (1): [10.1039/C5MD00380F]

2. Zhang D, Markoulides MS, Stepanovs D, Rydzik AM, El-Hussein A, Bon C, Kamps JJAG, Umland KD, Collins PM, Cahill ST, Wang DY, von Delft F, Brem J, McDonough MA, Schofield CJ..  (2018)  Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases.,  26  (11): [PMID:29655609] [10.1016/j.bmc.2018.02.043]

3. Yahiaoui S, Voos K, Haupenthal J, Wichelhaus TA, Frank D, Weizel L, Rotter M, Brunst S, Kramer JS, Proschak E, Ducho C, Hirsch AKH..  (2021)  N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB from Pseudomonas aeruginosa.,  12  (10.0): [PMID:34778771] [10.1039/D1MD00187F]

Source

Source(1):

• Scientific Literature