4-(((4-(2-ethylphenyl)benzo[b]thiophen-2-yl)methylamino)methyl)benzoic acid

ID: ALA3885068

PubChem CID: 134131043

Max Phase: Preclinical

Molecular Formula: C25H23NO2S

Molecular Weight: 401.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccccc1-c1cccc2sc(CNCc3ccc(C(=O)O)cc3)cc12

Standard InChI:  InChI=1S/C25H23NO2S/c1-2-18-6-3-4-7-21(18)22-8-5-9-24-23(22)14-20(29-24)16-26-15-17-10-12-19(13-11-17)25(27)28/h3-14,26H,2,15-16H2,1H3,(H,27,28)

Standard InChI Key:  YJFVBILVDPNENV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.5555   -4.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9666   -3.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5581   -3.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7371   -3.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3277   -3.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9709   -2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7970   -2.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089   -5.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100   -6.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3179   -6.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3185   -5.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0273   -5.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0264   -6.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7999   -6.6174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2798   -5.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8003   -5.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0970   -5.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5078   -5.2598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3193   -4.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0252   -3.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0264   -3.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3186   -2.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6082   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6104   -3.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7395   -4.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3291   -5.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4507   -3.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5589   -1.7118    0.0000 O   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
  4  7  1  0
  7  8  1  0
 10  9  1  0
 10 11  2  0
 14 11  1  0
 12 13  1  0
  9 12  2  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 16 18  1  0
 18 19  1  0
 12 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
 21 26  1  0
 19 27  1  0
 27  1  1  0
 26 28  1  0
  7 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3885068

   ---

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: 401.53

Molecular Weight (Monoisotopic): 401.1449

AlogP: 6.12

#Rotatable Bonds: 7

Polar Surface Area: 49.33

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.81

CX Basic pKa: 8.67

CX LogP: 4.06

CX LogD: 4.04

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -0.97

References

1. Hur W, Rosen H, Gray NS..  (2017)  A benzo[b]thiophene-based selective type 4 S1P receptor agonist.,  27  (1): [PMID:27894870] [10.1016/j.bmcl.2016.11.050]

Source

Source(1):

• Scientific Literature