N,N-dimethyl-2-(6-(5-(trifluoromethyl)thiophen-2-yl)-1H-pyrrolo[3,2-b]pyridin-1-yl)acetamide

ID: ALA4531750

PubChem CID: 124176291

Max Phase: Preclinical

Molecular Formula: C16H14F3N3OS

Molecular Weight: 353.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)C(=O)Cn1ccc2ncc(-c3ccc(C(F)(F)F)s3)cc21

Standard InChI:  InChI=1S/C16H14F3N3OS/c1-21(2)15(23)9-22-6-5-11-12(22)7-10(8-20-11)13-3-4-14(24-13)16(17,18)19/h3-8H,9H2,1-2H3

Standard InChI Key:  LPFCXGVNLRXWCM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.9513  -15.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501  -16.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582  -17.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564  -15.5346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3650  -15.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3698  -16.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498  -17.0069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6272  -16.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1421  -15.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4069  -17.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2072  -17.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4642  -18.7236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7504  -17.3374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9209  -19.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645  -18.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2421  -17.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944  -16.8395    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9471  -17.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551  -18.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1545  -17.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344  -17.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026  -16.6135    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6536  -18.0210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166  -17.3591    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 12 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531750

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.37

Molecular Weight (Monoisotopic): 353.0810

AlogP: 3.87

#Rotatable Bonds: 3

Polar Surface Area: 38.13

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.06

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -1.60

References

1. Chrovian CC, Soyode-Johnson A, Wall JL, Rech JC, Schoellerman J, Lord B, Coe KJ, Carruthers NI, Nguyen L, Jiang X, Koudriakova T, Balana B, Letavic MA..  (2019)  1H-Pyrrolo[3,2-b]pyridine GluN2B-Selective Negative Allosteric Modulators.,  10  (3): [PMID:30891123] [10.1021/acsmedchemlett.8b00542]

2. Chrovian CC,Soyode-Johnson A,Stenne B,Pippel DJ,Schoellerman J,Lord B,Needham AS,Xia C,Coe KJ,Sepassi K,Schoetens F,Scott B,Nguyen L,Jiang X,Koudriakova T,Balana B,Letavic MA.  (2020)  Design, Synthesis, and Preclinical Evaluation of 3-Methyl-6-(5-thiophenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-ones as Selective GluN2B Negative Allosteric Modulators for the Treatment of Mood Disorders.,  63  (17): [PMID:32787105] [10.1021/acs.jmedchem.9b02113]

Source

Source(1):

• Scientific Literature