(R)-N-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)picolinamide

ID: ALA551051

Cas Number: 827591-02-6

PubChem CID: 11416123

Max Phase: Preclinical

Molecular Formula: C18H16ClN3O

Molecular Weight: 325.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CCCc2c1[nH]c1ccc(Cl)cc21)c1ccccn1

Standard InChI:  InChI=1S/C18H16ClN3O/c19-11-7-8-14-13(10-11)12-4-3-6-15(17(12)21-14)22-18(23)16-5-1-2-9-20-16/h1-2,5,7-10,15,21H,3-4,6H2,(H,22,23)/t15-/m1/s1

Standard InChI Key:  WJQBOBGVBBZLJU-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -4.3018    3.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0163    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0163    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3018    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873    2.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873    3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    2.2495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    3.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4671    4.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    4.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1617    3.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973    3.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124    2.3358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    2.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    1.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    3.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4627    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502    1.6213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7308    3.7420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  5  1  0
  6  9  1  0
  7  8  1  0
 13  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 16 22  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA551051

   (R)-N-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)picolinamide

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: 325.80

Molecular Weight (Monoisotopic): 325.0982

AlogP: 4.02

#Rotatable Bonds: 2

Polar Surface Area: 57.78

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 2.10

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -1.07

References

1. Gudmundsson KS, Boggs SD, Sebahar PR, Richardson LD, Spaltenstein A, Golden P, Sethna PB, Brown KW, Moniri K, Harvey R, Romines KR..  (2009)  Tetrahydrocarbazole amides with potent activity against human papillomaviruses.,  19  (15): [PMID:19556128] [10.1016/j.bmcl.2009.06.001]

2. Okesli-Armlovich A, Gupta A, Jimenez M, Auld D, Liu Q, Bassik MC, Khosla C..  (2019)  Discovery of small molecule inhibitors of human uridine-cytidine kinase 2 by high-throughput screening.,  29  (18): [PMID:31420268] [10.1016/j.bmcl.2019.08.010]

3. Boschi D, Pippione AC, Sainas S, Lolli ML..  (2019)  Dihydroorotate dehydrogenase inhibitors in anti-infective drug research.,  183  [PMID:31557612] [10.1016/j.ejmech.2019.111681]

Source

Source(1):

• Scientific Literature