4,6-Dichloro-N-((5-(1,3-dimethylpyrazol-4-y1)-4-methy1-2-pyridyl)methyl)-1H-pyrrolo(3,2-c)pyridine-2-carboxamide

ID: ALA4874151

PubChem CID: 164627170

Max Phase: Preclinical

Molecular Formula: C20H18Cl2N6O

Molecular Weight: 429.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(CNC(=O)c2cc3c(Cl)nc(Cl)cc3[nH]2)ncc1-c1cn(C)nc1C

Standard InChI:  InChI=1S/C20H18Cl2N6O/c1-10-4-12(23-8-14(10)15-9-28(3)27-11(15)2)7-24-20(29)17-5-13-16(25-17)6-18(21)26-19(13)22/h4-6,8-9,25H,7H2,1-3H3,(H,24,29)

Standard InChI Key:  RAAZRTAWLIDXSI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.8988  -19.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8977  -20.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6057  -21.2166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154  -20.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125  -19.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039  -19.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015  -18.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910  -19.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1053  -18.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059  -18.5981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975  -19.3059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445  -19.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0848  -19.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124  -18.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0237  -21.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7308  -20.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4391  -21.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4404  -22.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -20.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8907  -21.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2278  -19.9870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268  -19.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4344  -20.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2457  -20.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6505  -19.8123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2379  -19.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4279  -19.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6419  -18.3975    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6561  -21.2240    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  2  0
 20 23  1  0
 22 21  1  0
 21 19  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874151

   ---

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: 429.31

Molecular Weight (Monoisotopic): 428.0919

AlogP: 4.21

#Rotatable Bonds: 4

Polar Surface Area: 88.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.24

CX Basic pKa: 4.41

CX LogP: 2.81

CX LogD: 2.80

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.47

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