4-(3,4-dichlorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

ID: ALA4091827

PubChem CID: 667722

Max Phase: Preclinical

Molecular Formula: C14H9Cl2NO2S

Molecular Weight: 326.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2sccc2n1Cc1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C14H9Cl2NO2S/c15-9-2-1-8(5-10(9)16)7-17-11-3-4-20-13(11)6-12(17)14(18)19/h1-6H,7H2,(H,18,19)

Standard InChI Key:  DPHWBTRBOKNJEB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   11.6085   -4.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7947   -4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5325   -5.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0918   -6.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9016   -6.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1561   -5.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4528   -6.8141    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8374   -7.1583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2471   -4.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5042   -3.5770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0237   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5128   -2.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2898   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2898   -3.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0761   -3.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5615   -2.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0814   -2.2509    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1988   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7930   -2.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7838   -3.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  4  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
 11 18  1  0
 18 19  2  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091827

   4-(3,4-Dichlorobenzyl)thieno[3,2-b]pyrrole-5-carboxylic acid

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: 326.20

Molecular Weight (Monoisotopic): 324.9731

AlogP: 4.76

#Rotatable Bonds: 3

Polar Surface Area: 42.23

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.75

Np Likeness Score: -2.01

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature