(Z)-7-[(1R,2S,5R)-2-(4a,5-Dihydro-quinoline-8-sulfonylamino)-5-fluoro-cyclopentyl]-hept-5-enoic acid

ID: ALA3706741

PubChem CID: 122197353

Max Phase: Preclinical

Molecular Formula: C21H25FN2O4S

Molecular Weight: 420.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCC/C=C\C[C@H]1[C@H](F)CC[C@@H]1NS(=O)(=O)c1cccc2cccnc12

Standard InChI:  InChI=1S/C21H25FN2O4S/c22-17-12-13-18(16(17)9-3-1-2-4-11-20(25)26)24-29(27,28)19-10-5-7-15-8-6-14-23-21(15)19/h1,3,5-8,10,14,16-18,24H,2,4,9,11-13H2,(H,25,26)/b3-1-/t16-,17+,18-/m0/s1

Standard InChI Key:  WQRIRZONRYDKCT-ALVNHBQLSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  1  0  0  0  0  0999 V2000
    4.4516   -4.2143    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761   -4.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8008   -4.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6271   -4.3475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5260   -5.4885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1024   -3.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -2.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6140   -4.9388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3142   -3.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5635   -3.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129   -4.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7276   -2.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3755   -3.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654   -3.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -5.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986    1.3867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0507   -6.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8627   -5.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530   -2.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892   -1.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1268   -1.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -1.5866    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1618    0.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1893   -2.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9002   -3.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482   -0.1749    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  3  1  0
  6  4  1  1
  7  6  1  0
  8  1  2  0
  9  1  2  0
 10  2  1  0
 11  3  1  0
 12 27  1  0
 13  7  1  0
 14 10  2  0
 15  6  1  0
 16 11  1  0
 17 12  2  0
 18  5  2  0
 19 16  2  0
 20 15  1  0
 21 25  1  0
 22 21  2  0
 13 23  1  1
 24 12  1  0
  7 25  1  6
 26 14  1  0
 27 29  1  0
 28 22  1  0
 29 28  1  0
 13 20  1  0
 26 11  2  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706741

   ---

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: 420.51

Molecular Weight (Monoisotopic): 420.1519

AlogP: 3.83

#Rotatable Bonds: 9

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.58

CX Basic pKa: 0.48

CX LogP: 3.21

CX LogD: 0.46

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -0.19

References

1. Klar U, Kuhnke J, Pletsch A, Rehwinkel H, Schreyer R.  (1995)  Novel prostanoid thromboxane A2 antagonists,  5  (12): [10.1016/0960-894X(95)00199-4]

Source

Source(1):

• Scientific Literature