4-(3-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylcarbamoyl)phenylsulfonamido)benzoic acid

ID: ALA605959

PubChem CID: 2203542

Max Phase: Preclinical

Molecular Formula: C23H19N3O5S2

Molecular Weight: 481.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ZINC 02849675 | MLS000693452|SMR000299999|4-{[(3-{[(3-cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amino]carbonyl}phenyl)sulfonyl]amino}benzoic acid|CHEMBL605959|BDBM50424|cid_2203542|HMS2769D21|ZINC 02849675|4-[[3-[(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)carbamoyl]phenyl]sulfonylamino]benzoic acid|4-[[3-[(3-cyano-4,5,6,7-tetrahydrobenzothiophen-2-yl)carbamoyl]phenyl]sulfonylamino]benzoic Acid|4-[[3-[[(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)amino]-oxomethyl]phenyl]sulfonylamino]bShow More⌵

Canonical SMILES:  N#Cc1c(NC(=O)c2cccc(S(=O)(=O)Nc3ccc(C(=O)O)cc3)c2)sc2c1CCCC2

Standard InChI:  InChI=1S/C23H19N3O5S2/c24-13-19-18-6-1-2-7-20(18)32-22(19)25-21(27)15-4-3-5-17(12-15)33(30,31)26-16-10-8-14(9-11-16)23(28)29/h3-5,8-12,26H,1-2,6-7H2,(H,25,27)(H,28,29)

Standard InChI Key:  GYKLQZOUNYFRKC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   10.5446   -1.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5446   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8302   -2.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8302   -1.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1157   -1.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1157   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311   -2.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8462   -1.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311   -1.2185    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0761   -3.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8212   -4.1226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0212   -1.8859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6087   -1.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -1.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0212   -0.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3712   -1.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462   -1.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337   -1.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462   -0.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3712   -0.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    0.2575    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8481    0.6700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4192   -0.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    1.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    2.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587    3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3712    2.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1337    3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587    1.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3712    3.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587    4.5443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1962    3.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 14  1  0
  5  4  1  0
 19 21  1  0
  7 10  1  0
 21 22  1  0
  5  6  2  0
 21 23  2  0
 10 11  3  0
 21 24  2  0
 22 25  1  0
 25 26  2  0
  8 12  1  0
 27 28  1  0
  1  2  1  0
 12 13  1  0
  1  4  1  0
 13 14  1  0
 25 30  1  0
 26 29  1  0
 29 27  2  0
 28 30  2  0
  2  3  1  0
 27 31  1  0
 13 15  2  0
 31 32  1  0
  3  6  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA605959

   4-[[3-[(3-cyano-4,5,6,7-tetrahydrobenzothiophen-2-yl)carbamoyl]phenyl]sulfonylamino]benzoic 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: 481.56

Molecular Weight (Monoisotopic): 481.0766

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 136.36

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.49

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: -2.17

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays