3-{(2,5-Dichloro-thiophene-3-sulfonyl)-[2-(4-fluoro-phenyl)-ethyl]-amino}-3-(1H-imidazol-4-yl)-propionic acid

ID: ALA368695

PubChem CID: 44390100

Max Phase: Preclinical

Molecular Formula: C18H16Cl2FN3O4S2

Molecular Weight: 492.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC(c1c[nH]cn1)N(CCc1ccc(F)cc1)S(=O)(=O)c1cc(Cl)sc1Cl

Standard InChI:  InChI=1S/C18H16Cl2FN3O4S2/c19-16-8-15(18(20)29-16)30(27,28)24(6-5-11-1-3-12(21)4-2-11)14(7-17(25)26)13-9-22-10-23-13/h1-4,8-10,14H,5-7H2,(H,22,23)(H,25,26)

Standard InChI Key:  OEZOBCNXXBNPAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.4375    0.9875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125    0.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    0.5833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542    0.9000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    0.5833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167    1.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500    1.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000   -0.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    2.0458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    3.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -0.3000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    1.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.9542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  4  1  0
  8  5  2  0
  9  7  1  0
 10  7  1  0
 11  9  1  0
 12  1  2  0
 13  1  2  0
 14  4  1  0
 15 10  1  0
 16 18  1  0
 17 11  2  0
 18  9  2  0
 19  3  1  0
 20 15  2  0
 21  8  1  0
 22 14  1  0
 23 27  1  0
 24 22  1  0
 25 15  1  0
 26 23  1  0
 27 30  2  0
 28 29  1  0
 29 24  2  0
 30 24  1  0
  6  8  1  0
 17 16  1  0
 23 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA368695

   3-[(2,5-dichlorothiophen-3-yl)sulfonyl-[2-(4-fluorophenyl)ethyl]amino]-3-(1H-imidazol-5-yl)propanoic 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: 492.38

Molecular Weight (Monoisotopic): 490.9943

AlogP: 4.37

#Rotatable Bonds: 9

Polar Surface Area: 103.36

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 6.17

CX LogP: 2.86

CX LogD: 1.65

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.15

References

1. Saha AK, End DW..  (2005)  Novel beta-(imidazol-4-yl)-beta-amino acids: solid-phase synthesis and study of their inhibitory activity against geranylgeranyl protein transferase type I.,  15  (6): [PMID:15745827] [10.1016/j.bmcl.2005.01.042]

Source

Source(1):

• Scientific Literature