(6-((Benzo[b]thiophen-2-ylmethyl)(pyridin-3-ylsulfonyl)-aminomethyl)pyridin-2-ylamino)acetic Acid Hydrochloride

ID: ALA4476670

PubChem CID: 66717335

Max Phase: Preclinical

Molecular Formula: C22H21ClN4O4S2

Molecular Weight: 468.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)CNc1cccc(CN(Cc2cc3ccccc3s2)S(=O)(=O)c2cccnc2)n1

Standard InChI:  InChI=1S/C22H20N4O4S2.ClH/c27-22(28)13-24-21-9-3-6-17(25-21)14-26(32(29,30)19-7-4-10-23-12-19)15-18-11-16-5-1-2-8-20(16)31-18;/h1-12H,13-15H2,(H,24,25)(H,27,28);1H

Standard InChI Key:  KHLSMGHQVRHYON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   25.4277  -26.6357    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.8635  -29.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0375  -29.1396    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4484  -29.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8941  -29.5589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8929  -30.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6092  -30.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3271  -30.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3243  -29.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6074  -29.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0355  -28.3156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7499  -27.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3180  -27.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3149  -27.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4673  -28.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0311  -26.6655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5937  -25.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5999  -26.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3104  -25.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0254  -25.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7391  -25.4189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4572  -25.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1667  -25.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8849  -25.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1623  -24.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5569  -29.1291    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2216  -27.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7740  -28.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3645  -29.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7755  -30.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6000  -30.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0118  -29.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5942  -28.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9  3  1  0
  3 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 12 15  1  0
 14 16  2  0
 16 20  1  0
 19 17  1  0
 17 18  2  0
 18 14  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 15 26  1  0
 26 29  1  0
 28 27  1  0
 27 15  2  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 468.56

Molecular Weight (Monoisotopic): 468.0926

AlogP: 3.58

#Rotatable Bonds: 9

Polar Surface Area: 112.49

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.98

CX Basic pKa: 5.67

CX LogP: 0.64

CX LogD: -0.67

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.84

References

1. Iwamura R, Tanaka M, Okanari E, Kirihara T, Odani-Kawabata N, Shams N, Yoneda K..  (2018)  Identification of a Selective, Non-Prostanoid EP2 Receptor Agonist for the Treatment of Glaucoma: Omidenepag and its Prodrug Omidenepag Isopropyl.,  61  (15): [PMID:29995405] [10.1021/acs.jmedchem.8b00808]

Source

Source(1):

• Scientific Literature