N-Cyclopropyl-6-(2-((2,6-dichloro-4-pyridyl)carbamoyl)hydrazino)-4-methylpyridine-2-carboxamide

ID: ALA4873977

PubChem CID: 164627572

Max Phase: Preclinical

Molecular Formula: C16H16Cl2N6O2

Molecular Weight: 395.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NNC(=O)Nc2cc(Cl)nc(Cl)c2)nc(C(=O)NC2CC2)c1

Standard InChI:  InChI=1S/C16H16Cl2N6O2/c1-8-4-11(15(25)19-9-2-3-9)21-14(5-8)23-24-16(26)20-10-6-12(17)22-13(18)7-10/h4-7,9H,2-3H2,1H3,(H,19,25)(H,21,23)(H2,20,22,24,26)

Standard InChI Key:  WZDWGFOENNUCKD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   16.1773   -3.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1762   -4.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8842   -4.7366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5939   -4.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5911   -3.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8824   -3.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3022   -4.7347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0093   -4.3249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7176   -4.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4247   -4.3227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7189   -5.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8800   -2.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1331   -4.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1299   -5.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8375   -5.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5455   -5.5457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5416   -4.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8335   -4.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2472   -4.3121    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.8383   -6.7727    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4681   -4.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7608   -4.3265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4675   -5.5529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7614   -3.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1720   -2.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3548   -2.8052    0.0000 C   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
 21 23  2  0
 22 24  1  0
 25 24  1  0
 26 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873977

   ---

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: 395.25

Molecular Weight (Monoisotopic): 394.0712

AlogP: 3.13

#Rotatable Bonds: 5

Polar Surface Area: 108.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.88

CX Basic pKa: 3.41

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: -1.76

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