2-(3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propylthio)benzoic acid

ID: ALA3322500

Cas Number: 325850-81-5

PubChem CID: 3114900

Product Number: G288503, Order Now?

Max Phase: Preclinical

Molecular Formula: C22H17NO4S

Molecular Weight: 391.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1SCCCN1C(=O)c2cccc3cccc(c23)C1=O

Standard InChI:  InChI=1S/C22H17NO4S/c24-20-16-9-3-6-14-7-4-10-17(19(14)16)21(25)23(20)12-5-13-28-18-11-2-1-8-15(18)22(26)27/h1-4,6-11H,5,12-13H2,(H,26,27)

Standard InChI Key:  GMVZUCHUOYUMLL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    2.3800   -7.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -8.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0869   -9.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -8.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5030   -9.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2113   -8.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2065   -7.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937   -7.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975   -7.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944   -6.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7883   -6.3286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0838   -6.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -7.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2006   -6.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730   -6.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7838   -5.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4892   -5.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4847   -4.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901   -3.8692    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1856   -3.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8960   -2.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8918   -1.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1813   -1.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736   -1.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4812   -2.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738   -3.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0628   -2.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -3.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
 13  1  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  8  1  0
 10 14  2  0
 12 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  1  0
 26 28  2  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3322500

   GRI 977143

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: 391.45

Molecular Weight (Monoisotopic): 391.0878

AlogP: 4.32

#Rotatable Bonds: 6

Polar Surface Area: 74.68

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.41

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 0.55

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.38

Np Likeness Score: -0.97

References

1. Patil R, Fells JI, Szabó E, Lim KG, Norman DD, Balogh A, Patil S, Strobos J, Miller DD, Tigyi GJ..  (2014)  Design and synthesis of sulfamoyl benzoic acid analogues with subnanomolar agonist activity specific to the LPA2 receptor.,  57  (16): [PMID:25100502] [10.1021/jm5007116]

Source

Source(1):

• Scientific Literature