5-Chloro-1-((1R)-1-(3-cyanophenyl)ethyl)-2-imino-1,2-dihydropyridine-3-carboxamide

ID: ALA3799292

Cas Number: 1191908-24-3

PubChem CID: 44470113

Max Phase: Preclinical

Molecular Formula: C15H13ClN4O

Molecular Weight: 300.75

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tp-009 | CHEMBL3799292|ADRA1D receptor antagonist 1 (free base)|SCHEMBL1002017|Tp-009|BDBM50164687|ADRA1D receptor antagonist 1 free base|HY-148252|CS-0617260|1191908-24-3

Canonical SMILES:  C[C@H](c1cccc(C#N)c1)n1cc(Cl)cc(C(N)=O)c1=N

Standard InChI:  InChI=1S/C15H13ClN4O/c1-9(11-4-2-3-10(5-11)7-17)20-8-12(16)6-13(14(20)18)15(19)21/h2-6,8-9,18H,1H3,(H2,19,21)/t9-/m1/s1

Standard InChI Key:  CDJPHTNUARAVMH-SECBINFHSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    2.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982    1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972    0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4971   -0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980   -1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1980   -2.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -4.1966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351   -3.6026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -3.5994    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  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  3  0
 10 13  2  0
  6 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799292

   (R)-9s

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

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: 300.75

Molecular Weight (Monoisotopic): 300.0778

AlogP: 2.20

#Rotatable Bonds: 3

Polar Surface Area: 95.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.44

CX LogP: 1.69

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: -1.40

References

1. Sakauchi N, Kohara Y, Sato A, Suzaki T, Imai Y, Okabe Y, Imai S, Saikawa R, Nagabukuro H, Kuno H, Fujita H, Kamo I, Yoshida M..  (2016)  Discovery of 5-Chloro-1-(5-chloro-2-(methylsulfonyl)benzyl)-2-imino-1,2-dihydropyridine-3-carboxamide (TAK-259) as a Novel, Selective, and Orally Active α1D Adrenoceptor Antagonist with Antiurinary Frequency Effects: Reducing Human Ether-a-go-go-Related Gene (hERG) Liabilities.,  59  (7): [PMID:26954848] [10.1021/acs.jmedchem.5b01528]

2. SGC Frankfurt.  (2021)  Data for DCP probe (R)-9s,  [10.6019/CHEMBL4507301]

Source

Source(2):

• Scientific Literature
• Donated Chemical Probes - SGC Frankfurt