2-(3,4-Dichloropheny1)-N-((5-(1,3-dimethylpyrazol-4-y1)-4-methyl)-2-pyridy)lmethyl)acetamide

ID: ALA4876986

PubChem CID: 164626836

Max Phase: Preclinical

Molecular Formula: C20H20Cl2N4O

Molecular Weight: 403.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(CNC(=O)Cc2ccc(Cl)c(Cl)c2)ncc1-c1cn(C)nc1C

Standard InChI:  InChI=1S/C20H20Cl2N4O/c1-12-6-15(23-10-16(12)17-11-26(3)25-13(17)2)9-24-20(27)8-14-4-5-18(21)19(22)7-14/h4-7,10-11H,8-9H2,1-3H3,(H,24,27)

Standard InChI Key:  FIFLHWHKXGREIU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.1889  -25.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878  -25.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8958  -26.2519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6055  -25.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027  -25.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940  -24.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916  -23.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811  -24.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954  -23.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961  -23.6333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876  -24.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346  -24.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749  -24.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0026  -23.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3138  -26.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209  -25.8402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7293  -26.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7305  -27.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4363  -25.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1447  -26.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1416  -27.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8491  -27.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5571  -27.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5532  -26.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8451  -25.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500  -28.2879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2660  -27.4675    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  1  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 11 13  1  0
  9 14  1  0
  4 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876986

   ---

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: 403.31

Molecular Weight (Monoisotopic): 402.1014

AlogP: 4.26

#Rotatable Bonds: 5

Polar Surface Area: 59.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: 4.41

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.64

References

1. Mammoliti O, Palisse A, Joannesse C, El Bkassiny S, Allart B, Jaunet A, Menet C, Coornaert B, Sonck K, Duys I, Clément-Lacroix P, Oste L, Borgonovi M, Wakselman E, Christophe T, Houvenaghel N, Jans M, Heckmann B, Sanière L, Brys R..  (2021)  Discovery of the S1P2 Antagonist GLPG2938 (1-[2-Ethoxy-6-(trifluoromethyl)-4-pyridyl]-3-[[5-methyl-6-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]pyridazin-3-yl]methyl]urea), a Preclinical Candidate for the Treatment of Idiopathic Pulmonary Fibrosis.,  64  (9.0): [PMID:33939425] [10.1021/acs.jmedchem.1c00138]

2. Osada, Makoto M, Yatomi, Yutaka Y, Ohmori, Tsukasa T, Ikeda, Hitoshi H and Ozaki, Yukio Y.  2002-12-06  Enhancement of sphingosine 1-phosphate-induced migration of vascular endothelial cells and smooth muscle cells by an EDG-5 antagonist.  [PMID:12445827]

3. Sanna, M Germana MG and 10 more authors.  2004-04-02  Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.  [PMID:14732717]

4. Deng, Hongfeng H and 6 more authors.  2013-10-10  Discovery of Clinical Candidate GSK1842799 As a Selective S1P1 Receptor Agonist (Prodrug) for Multiple Sclerosis.  [PMID:24900589]

5. Demont, Emmanuel H EH and 22 more authors.  2016-02-11  Discovery of Tetrahydropyrazolopyridine as Sphingosine 1-Phosphate Receptor 3 (S1P3)-Sparing S1P1 Agonists Active at Low Oral Doses.  [PMID:26751273]

6. Scott, F L FL and 12 more authors.  2016-06  Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5 ) agonist with autoimmune disease-modifying activity.  [PMID:26990079]

Source

Source(1):

• Scientific Literature