2-(4-bromo-2-((4-oxo-3-(pyridin-2-ylmethyl)-2-thioxothiazolidin-5-ylidene)methyl)phenoxy)acetic acid

ID: ALA4284695

PubChem CID: 145991031

Max Phase: Preclinical

Molecular Formula: C18H13BrN2O4S2

Molecular Weight: 465.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)COc1ccc(Br)cc1/C=C1\SC(=S)N(Cc2ccccn2)C1=O

Standard InChI:  InChI=1S/C18H13BrN2O4S2/c19-12-4-5-14(25-10-16(22)23)11(7-12)8-15-17(24)21(18(26)27-15)9-13-3-1-2-6-20-13/h1-8H,9-10H2,(H,22,23)/b15-8-

Standard InChI Key:  DZPVIZZFQXTDHO-NVNXTCNLSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.6978   -3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966   -4.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047   -4.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -4.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115   -3.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -2.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045   -5.3309    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -2.0592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9851   -2.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2761   -1.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875   -2.8806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -2.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5261   -3.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5300   -4.0935    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3090   -4.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7867   -3.6786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3027   -3.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5652   -5.1185    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5515   -2.2409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6038   -3.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0158   -4.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6078   -5.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0191   -5.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8371   -5.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2421   -5.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -4.3728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 16 19  2  0
 18 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4284695

   ---

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: 465.35

Molecular Weight (Monoisotopic): 463.9500

AlogP: 3.71

#Rotatable Bonds: 6

Polar Surface Area: 79.73

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.80

CX Basic pKa: 4.14

CX LogP: 2.36

CX LogD: 0.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -2.13

References

1. Lough L, Sherman D, Ni E, Young LM, Hao B, Cardozo T..  (2018)  Chemical probes of Skp2-mediated p27 ubiquitylation and degradation.,  9  (7): [PMID:30108998] [10.1039/C8MD00140E]

Source

Source(1):

• Scientific Literature