(S)-2-(4-fluorophenyl)-N-((3S,4S)-4-(methylsulfonyl)chroman-3-yl)propenamide

ID: ALA5266235

Max Phase: Preclinical

Molecular Formula: C19H20FNO4S

Molecular Weight: 377.44

Names and Identifiers

Canonical SMILES:  C[C@H](C(=O)N[C@H]1COc2ccccc2[C@@H]1S(C)(=O)=O)c1ccc(F)cc1

Standard InChI:  InChI=1S/C19H20FNO4S/c1-12(13-7-9-14(20)10-8-13)19(22)21-16-11-25-17-6-4-3-5-15(17)18(16)26(2,23)24/h3-10,12,16,18H,11H2,1-2H3,(H,21,22)/t12-,16-,18-/m0/s1

Standard InChI Key:  DKLUNKKXISSMIY-IWEFOYFVSA-N

Molfile:  

 
     RDKit          2D

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   -3.9295   -1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295   -1.5949    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    0.8803    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    1.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3735    1.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  0
  4  9  2  0
  9 10  1  0
 10  1  2  0
  7 11  1  1
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 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
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 18 20  2  0
 21 15  2  0
 20 21  1  0
 14 22  1  1
  8 23  1  6
 23 24  1  0
 23 25  2  0
 23 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5266235

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.44

Molecular Weight (Monoisotopic): 377.1097

AlogP: 2.59

#Rotatable Bonds: 4

Polar Surface Area: 72.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.89

Np Likeness Score: -0.63

References

1. Dickson L, Teall M, Chevalier E, Cheung T, Liwicki GM, Mack S, Stephenson A, White K, Fosbeary R, Harrison DC, Brice NL, Doyle K, Ciccocioppo R, Wu C, Almond S, Patel TR, Mitchell P, Barnes M, Ayscough AP, Dawson LA, Carlton M, Bürli RW..  (2023)  Discovery of CVN636: A Highly Potent, Selective, and CNS Penetrant mGluR₇ Allosteric Agonist.,  14  (4): [PMID:37077399] [10.1021/acsmedchemlett.2c00529]

Source

Source(1):

• Scientific Literature