2-mercapto-3-(2-(naphthalen-2-ylmethyl)phenyl)acrylic acid

ID: ALA4128221

PubChem CID: 134817541

Max Phase: Preclinical

Molecular Formula: C20H16O2S

Molecular Weight: 320.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)/C(S)=C/c1ccccc1Cc1ccc2ccccc2c1

Standard InChI:  InChI=1S/C20H16O2S/c21-20(22)19(23)13-18-8-4-3-7-17(18)12-14-9-10-15-5-1-2-6-16(15)11-14/h1-11,13,23H,12H2,(H,21,22)/b19-13-

Standard InChI Key:  LALSQKFPBIDRFB-UYRXBGFRSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    7.6271  -20.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3348  -20.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0425  -20.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3348  -19.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194  -20.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271  -21.6184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2117  -20.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046  -20.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7973  -20.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969  -21.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5096  -22.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2139  -21.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5062  -19.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7993  -19.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031  -18.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971  -17.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952  -19.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885  -19.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892  -18.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6805  -17.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705  -18.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738  -19.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6831  -19.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  8 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4128221

   ---

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: 320.41

Molecular Weight (Monoisotopic): 320.0871

AlogP: 4.79

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: 0.02

References

1. 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]

Source

Source(1):

• Scientific Literature