1-(2,6-Dichloro-4-pyridy1)-3-((6-(hydroxymethyl)-4-methyl-2-pyridyl)amino)urea

ID: ALA4870007

PubChem CID: 164621519

Max Phase: Preclinical

Molecular Formula: C13H13Cl2N5O2

Molecular Weight: 342.19

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(CO)nc(NNC(=O)Nc2cc(Cl)nc(Cl)c2)c1

Standard InChI:  InChI=1S/C13H13Cl2N5O2/c1-7-2-9(6-21)16-12(3-7)19-20-13(22)17-8-4-10(14)18-11(15)5-8/h2-5,21H,6H2,1H3,(H,16,19)(H2,17,18,20,22)

Standard InChI Key:  KEDSMDCNCYBPFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   14.4150   -8.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4138   -8.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1219   -9.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8316   -8.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8287   -8.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1201   -7.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5399   -9.3737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2470   -8.9640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9553   -9.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6624   -8.9617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9566  -10.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1177   -6.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3707   -9.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3676  -10.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0751  -10.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7832  -10.1847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7793   -9.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0712   -8.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4849   -8.9511    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.0760  -11.4117    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.7058   -9.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -8.9655    0.0000 O   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
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
 15 20  1  0
  2 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870007

   ---

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: 342.19

Molecular Weight (Monoisotopic): 341.0446

AlogP: 2.73

#Rotatable Bonds: 4

Polar Surface Area: 99.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.88

CX Basic pKa: 5.96

CX LogP: 2.61

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: -1.42

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