2-chloro-4-(5-((3-cyano-3a,4,5,6,7,7a-hexahydrobenzo[b]thiophen-2-ylimino)methyl)furan-2-yl)benzoic acid

ID: ALA378860

PubChem CID: 44415075

Max Phase: Preclinical

Molecular Formula: C21H17ClN2O3S

Molecular Weight: 412.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1=C(/N=C\c2ccc(-c3ccc(C(=O)O)c(Cl)c3)o2)SC2CCCCC12

Standard InChI:  InChI=1S/C21H17ClN2O3S/c22-17-9-12(5-7-15(17)21(25)26)18-8-6-13(27-18)11-24-20-16(10-23)14-3-1-2-4-19(14)28-20/h5-9,11,14,19H,1-4H2,(H,25,26)/b24-11-

Standard InChI Key:  KIBZYGPSCVIUCQ-MYKKPKGFSA-N

Molfile:  

     RDKit          2D

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   -2.5850  -23.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1522  -23.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0486  -24.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9355  -25.2904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073  -24.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450  -21.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459  -22.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139  -23.5672    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2322  -24.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349  -23.8449    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303  -25.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2285  -25.9206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910  -23.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667  -23.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2092  -23.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824  -22.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048  -22.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8597  -22.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0631  -21.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  9 12  1  0
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  2 15  1  0
  3 17  1  0
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 20 21  3  0
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 22 23  1  0
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 24 25  1  0
 25 26  1  0
 26 27  1  0
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA378860

   2-chloro-4-[5-[(Z)-(3-cyano-3a,4,5,6,7,7a-hexahydro-1-benzothiophen-2-yl)iminomethyl]furan-2-yl]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: 412.90

Molecular Weight (Monoisotopic): 412.0648

AlogP: 5.76

#Rotatable Bonds: 4

Polar Surface Area: 86.59

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.91

CX Basic pKa: 1.47

CX LogP: 4.98

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.82

References

1. Schepetkin IA, Khlebnikov AI, Kirpotina LN, Quinn MT..  (2006)  Novel small-molecule inhibitors of anthrax lethal factor identified by high-throughput screening.,  49  (17): [PMID:16913712] [10.1021/jm0605132]

Source

Source(1):

• Scientific Literature