2-Benzyloxy-5-(4-fluoro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]-pyridin-4-one

ID: ALA2426615

PubChem CID: 53246490

Max Phase: Preclinical

Molecular Formula: C19H15FN2O2S

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2sc(OCc3ccccc3)nc2CCN1c1ccc(F)cc1

Standard InChI:  InChI=1S/C19H15FN2O2S/c20-14-6-8-15(9-7-14)22-11-10-16-17(18(22)23)25-19(21-16)24-12-13-4-2-1-3-5-13/h1-9H,10-12H2

Standard InChI Key:  ZYFKTOSKEONTMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   25.7564  -12.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4733  -12.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4705  -11.5906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7547  -11.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0412  -12.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0379  -11.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2524  -11.3456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.7703  -12.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2579  -12.6801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9448  -12.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5350  -12.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7095  -12.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2973  -12.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4725  -12.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0619  -12.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4820  -13.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3054  -13.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7520  -10.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1838  -11.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8974  -11.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6103  -11.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6077  -10.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8862   -9.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1763  -10.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3204   -9.9308    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  4 18  2  0
  3 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2426615

   5-(4-Fluorophenyl)-2-phenylmethoxy-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one

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: 354.41

Molecular Weight (Monoisotopic): 354.0838

AlogP: 4.06

#Rotatable Bonds: 4

Polar Surface Area: 42.43

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.18

CX LogD: 4.18

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.37

References

1. Bartolomé-Nebreda JM, Conde-Ceide S, Delgado F, Iturrino L, Pastor J, Pena MÁ, Trabanco AA, Tresadern G, Wassvik CM, Stauffer SR, Jadhav S, Gogi K, Vinson PN, Noetzel MJ, Days E, Weaver CD, Lindsley CW, Niswender CM, Jones CK, Conn PJ, Rombouts F, Lavreysen H, Macdonald GJ, Mackie C, Steckler T..  (2013)  Dihydrothiazolopyridone derivatives as a novel family of positive allosteric modulators of the metabotropic glutamate 5 (mGlu5) receptor.,  56  (18): [PMID:23947773] [10.1021/jm400650w]

Source

Source(1):

• Scientific Literature