2-chloro-5-(5-((3-oxobenzo[b]thiophen-2(3H)-ylidene)methyl)furan-2-yl)benzoic acid

ID: ALA4790102

PubChem CID: 1824858

Max Phase: Preclinical

Molecular Formula: C20H11ClO4S

Molecular Weight: 382.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(-c2ccc(/C=C3\Sc4ccccc4C3=O)o2)ccc1Cl

Standard InChI:  InChI=1S/C20H11ClO4S/c21-15-7-5-11(9-14(15)20(23)24)16-8-6-12(25-16)10-18-19(22)13-3-1-2-4-17(13)26-18/h1-10H,(H,23,24)/b18-10-

Standard InChI Key:  ZPWFYRKGVDZJMU-ZDLGFXPLSA-N

Molfile:  

 
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    0.6124   -8.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204   -8.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -7.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -7.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0275   -8.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105   -8.7545    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2942   -8.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -7.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624   -6.6453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1114   -8.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -8.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1849   -9.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924  -10.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -9.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3297   -8.8782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2043  -10.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2041  -10.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116  -11.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6197  -10.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6159  -10.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9079   -9.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3229   -9.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0326  -10.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3188   -8.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285  -11.3071    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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 21 23  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790102

   2-chloro-5-{5-[(Z)-(3-oxo-1-benzothiophen-2(3H)-ylidene)methyl]furan-2-yl}benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.82

Molecular Weight (Monoisotopic): 382.0067

AlogP: 5.63

#Rotatable Bonds: 3

Polar Surface Area: 67.51

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.94

CX Basic pKa: ┄

CX LogP: 4.57

CX LogD: 1.08

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -1.24

References

1. Hou X,Sun JP,Ge L,Liang X,Li K,Zhang Y,Fang H.  (2020)  Inhibition of striatal-enriched protein tyrosine phosphatase by targeting computationally revealed cryptic pockets.,  190  [PMID:32078861] [10.1016/j.ejmech.2020.112131]

2. Lazinski LM, Royal G, Robin M, Maresca M, Haudecoeur R..  (2022)  Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives.,  65  (19.0): [PMID:36126323] [10.1021/acs.jmedchem.2c01150]

Source

Source(1):

• Scientific Literature