3-(4-(5-chloro-2-fluorobenzyl)piperazin-1-yl)-N-cyclopropylpyrido[4,3-b]pyrazin-2-amine

ID: ALA3719416

PubChem CID: 118308638

Max Phase: Preclinical

Molecular Formula: C21H22ClFN6

Molecular Weight: 412.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1ccc(Cl)cc1CN1CCN(c2nc3cnccc3nc2NC2CC2)CC1

Standard InChI:  InChI=1S/C21H22ClFN6/c22-15-1-4-17(23)14(11-15)13-28-7-9-29(10-8-28)21-20(25-16-2-3-16)26-18-5-6-24-12-19(18)27-21/h1,4-6,11-12,16H,2-3,7-10,13H2,(H,25,26)

Standard InChI Key:  SZEKFAIEHFMLBA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -7.4661    0.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4661   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1671   -1.8055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1671    1.1945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680    0.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5690   -1.8055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700    0.4445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5690    1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7652   -1.8055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7652    1.1945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7652    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0642    3.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3632    2.6945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3632    1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0642    0.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9613    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7651   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5151   -4.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0151   -4.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9613    1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2603    0.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5594    1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5594    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2604    3.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2604    4.9445    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2603   -1.0555    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  2 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16  1  1  0
  1 19  1  0
 12 20  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
 19 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 19  1  0
 27 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA3719416

   ---

2. Parent:

   

   ALA3719416

   3-[4-[(5-chloro-2-fluorophenyl)methyl]piperazin-1-yl]-N-cyclopropylpyrido[3,4-b]pyrazin-2-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 412.90

Molecular Weight (Monoisotopic): 412.1579

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 57.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.98

CX LogP: 3.64

CX LogD: 3.62

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -2.05

References

1. Sun H, Monenschein H, Schiffer HH, Reichard HA, Kikuchi S, Hopkins M, Macklin TK, Hitchcock S, Adams M, Green J, Brown J, Murphy ST, Kaushal N, Collia DR, Moore S, Ray WJ, English NM, Carlton MBL, Brice NL..  (2021)  First-Time Disclosure of CVN424, a Potent and Selective GPR6 Inverse Agonist for the Treatment of Parkinson's Disease: Discovery, Pharmacological Validation, and Identification of a Clinical Candidate.,  64  (14.0): [PMID:33861086] [10.1021/acs.jmedchem.0c02081]

Source

Source(1):

• Scientific Literature