Methyl 4-(3-Acetyl-4-hydroxy-5-oxo-1-phenethyl-2,5-dihydro-1Hpyrrol-2-yl)benzoate

ID: ALA3237303

PubChem CID: 73335991

Max Phase: Preclinical

Molecular Formula: C22H21NO5

Molecular Weight: 379.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(C2C(C(C)=O)=C(O)C(=O)N2CCc2ccccc2)cc1

Standard InChI:  InChI=1S/C22H21NO5/c1-14(24)18-19(16-8-10-17(11-9-16)22(27)28-2)23(21(26)20(18)25)13-12-15-6-4-3-5-7-15/h3-11,19,25H,12-13H2,1-2H3

Standard InChI Key:  CPBYAEZNUJSDLB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.3889  -14.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056  -13.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1099  -13.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265  -12.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5388  -13.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5345  -13.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8179  -14.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766  -13.9717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4278  -15.2120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9267  -13.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2554  -12.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5037  -11.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3287  -11.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5901  -12.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9335  -14.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6513  -14.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6582  -15.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3760  -15.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3827  -16.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6718  -16.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9539  -16.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9471  -15.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3768  -12.9904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8081  -11.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0133  -11.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936  -11.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3427  -10.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609  -15.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 10 15  1  0
 14 23  2  0
 13 24  1  0
 25 26  2  0
 25 27  1  0
 12 25  1  0
  5 11  1  0
  9 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3237303

   Methyl 4-(3-acetyl-4-hydroxy-5-oxo-1-phenethyl-2,5-dihydro-1H-pyrrol-2-yl)benzoate

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: 379.41

Molecular Weight (Monoisotopic): 379.1420

AlogP: 3.00

#Rotatable Bonds: 6

Polar Surface Area: 83.91

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.66

CX Basic pKa: ┄

CX LogP: 2.84

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.78

Np Likeness Score: -0.73

References

1. Zimmerman SS, Khatri A, Garnier-Amblard EC, Mullasseril P, Kurtkaya NL, Gyoneva S, Hansen KB, Traynelis SF, Liotta DC..  (2014)  Design, synthesis, and structure-activity relationship of a novel series of GluN2C-selective potentiators.,  57  (6): [PMID:24512267] [10.1021/jm401695d]

Source

Source(1):

• Scientific Literature