N-(5-(2,6-dichlorophenyl)-1,3,4-thiadiazol-2-yl)-4-(2-hydroxyethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxamide

ID: ALA3797865

PubChem CID: 127047085

Max Phase: Preclinical

Molecular Formula: C19H16Cl2N4O3S

Molecular Weight: 451.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nnc(-c2c(Cl)cccc2Cl)s1)c1ccc2c(c1)N(CCO)CCO2

Standard InChI:  InChI=1S/C19H16Cl2N4O3S/c20-12-2-1-3-13(21)16(12)18-23-24-19(29-18)22-17(27)11-4-5-15-14(10-11)25(6-8-26)7-9-28-15/h1-5,10,26H,6-9H2,(H,22,24,27)

Standard InChI Key:  YUHVXHBEFUPECH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -5.3425    5.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049    3.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    3.1351    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5599    4.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8097    5.5489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0524    4.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067    3.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7610    2.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2603    2.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0480    4.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3363    5.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8370    5.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2660    6.4292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -9.1305    1.7558    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6028    4.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 13 12  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 12 18  1  0
 15 19  1  0
  8 20  2  0
  6 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  6  1  0
 25 26  1  0
 21 27  1  0
 19 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797865

   ---

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: 451.34

Molecular Weight (Monoisotopic): 450.0320

AlogP: 3.96

#Rotatable Bonds: 5

Polar Surface Area: 87.58

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.66

CX Basic pKa: ┄

CX LogP: 3.85

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -1.89

References

1. Lee EC, Futatsugi K, Arcari JT, Bahnck K, Coffey SB, Derksen DR, Kalgutkar AS, Loria PM, Sharma R..  (2016)  Optimization of amide-based EP3 receptor antagonists.,  26  (11): [PMID:27107947] [10.1016/j.bmcl.2016.04.009]

Source

Source(1):

• Scientific Literature