2-(5-chlorothiophen-2-yl)-N-(1-(4-((S)-1-(dimethylamino)ethyl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)ethene-1-sulfonamide

ID: ALA5286872

Max Phase: Preclinical

Molecular Formula: C20H23ClFN3O3S2

Molecular Weight: 472.01

Names and Identifiers

Canonical SMILES:  C[C@@H](c1ccc(N2CCC(NS(=O)(=O)/C=C/c3ccc(Cl)s3)C2=O)c(F)c1)N(C)C

Standard InChI:  InChI=1S/C20H23ClFN3O3S2/c1-13(24(2)3)14-4-6-18(16(22)12-14)25-10-8-17(20(25)26)23-30(27,28)11-9-15-5-7-19(21)29-15/h4-7,9,11-13,17,23H,8,10H2,1-3H3/b11-9+/t13-,17?/m0/s1

Standard InChI Key:  AFDHTIFDRFSZDA-KFTKHCSHSA-N

Molfile:  

 
     RDKit          2D

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   -1.8076   -1.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823   -2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033   -1.9626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220   -2.5010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0009   -2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -2.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -2.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634   -1.4382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558   -0.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6512    0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    0.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2384   -1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9215   -1.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7118   -1.7614    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.0045    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    1.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736    2.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118    1.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6481    2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    2.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -1.3778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 18 19  2  0
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  1 21  2  0
 21 22  1  0
 17 23  1  0
 15 24  1  0
 24 25  1  0
 24 26  1  1
 25 27  1  0
 25 28  1  0
  6 29  2  0
  6 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286872

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.01

Molecular Weight (Monoisotopic): 471.0853

AlogP: 3.86

#Rotatable Bonds: 7

Polar Surface Area: 69.72

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.22

CX Basic pKa: 8.83

CX LogP: 2.45

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -1.73

References

1. Patel NR, Patel DV, Murumkar PR, Yadav MR..  (2016)  Contemporary developments in the discovery of selective factor Xa inhibitors: A review.,  121  [PMID:27322757] [10.1016/j.ejmech.2016.05.039]

Source

Source(1):

• Scientific Literature