Ethyl 4-(1-(2-(1H-Indol-3-yl)ethyl)-3-acetyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)-3-hydroxybenzoate

ID: ALA3237295

PubChem CID: 90035960

Max Phase: Preclinical

Molecular Formula: C25H24N2O6

Molecular Weight: 448.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(C2C(C(C)=O)=C(O)C(=O)N2CCc2c[nH]c3ccccc23)c(O)c1

Standard InChI:  InChI=1S/C25H24N2O6/c1-3-33-25(32)15-8-9-18(20(29)12-15)22-21(14(2)28)23(30)24(31)27(22)11-10-16-13-26-19-7-5-4-6-17(16)19/h4-9,12-13,22,26,29-30H,3,10-11H2,1-2H3

Standard InChI Key:  CNXFBAHAJJGIJV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    3.9267   -4.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271   -4.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162   -3.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -2.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -3.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2079   -4.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1029   -3.2267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3234   -2.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3236   -2.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1029   -1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846   -2.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4040   -2.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561   -1.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7463   -0.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9120   -2.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561   -4.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1577   -4.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109   -6.2816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -5.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109   -4.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -5.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8999   -4.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6095   -5.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6095   -6.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8999   -6.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -6.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -4.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927   -4.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -5.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918   -4.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3775   -4.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3409   -4.6082    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  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  7 11  1  0
 11 12  2  0
 10 13  1  0
 14 15  2  0
 14 16  1  0
  9 14  1  0
 17 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 19 27  1  0
 22 27  2  0
 18 21  1  0
  7 17  1  0
  3  8  1  0
  6 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  1  0
 31 32  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3237295

   ethyl 4-[3-acetyl-4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-oxo-2H-pyrrol-2-yl]-3-hydroxybenzoate

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: 448.48

Molecular Weight (Monoisotopic): 448.1634

AlogP: 3.58

#Rotatable Bonds: 7

Polar Surface Area: 119.93

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: ┄

CX LogP: 3.00

CX LogD: 2.98

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: -0.44

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