(S)-6,7-Dichloro-9-(1-methyl-1H-pyrazol-3-yl)-2-prolyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

ID: ALA5093487

PubChem CID: 166633070

Max Phase: Preclinical

Molecular Formula: C20H21Cl2N5O

Molecular Weight: 418.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1ccc(-c2cc(Cl)c(Cl)c3[nH]c4c(c23)CN(C(=O)[C@@H]2CCCN2)CC4)n1

Standard InChI:  InChI=1S/C20H21Cl2N5O/c1-26-7-4-15(25-26)11-9-13(21)18(22)19-17(11)12-10-27(8-5-14(12)24-19)20(28)16-3-2-6-23-16/h4,7,9,16,23-24H,2-3,5-6,8,10H2,1H3/t16-/m0/s1

Standard InChI Key:  QGBUROBGVSVRSX-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   15.4097   -4.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4085   -5.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1166   -5.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1148   -3.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8234   -4.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8282   -5.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6082   -5.4259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6005   -4.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0842   -4.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8910   -4.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2205   -3.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7368   -3.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9236   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7005   -5.5900    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.1176   -6.4081    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.1092   -3.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7688   -2.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5140   -1.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6967   -1.8828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4467   -2.6608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2144   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0655   -2.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8778   -2.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5820   -1.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4243   -3.0339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1693   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0799   -1.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2797   -1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  2 14  1  0
  3 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
  4 16  1  0
 19 21  1  0
 12 22  1  0
 23 22  1  6
 22 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5093487

   ---

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: 418.33

Molecular Weight (Monoisotopic): 417.1123

AlogP: 3.51

#Rotatable Bonds: 2

Polar Surface Area: 65.95

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.94

CX Basic pKa: 9.82

CX LogP: 2.77

CX LogD: 0.41

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -1.21

References

1. Tan J, Wu B, Chen T, Fan C, Zhao J, Xiong C, Feng C, Xiao R, Ding C, Tang W, Zhang A..  (2021)  Synthesis and Pharmacological Evaluation of Tetrahydro-γ-carboline Derivatives as Potent Anti-inflammatory Agents Targeting Cyclic GMP-AMP Synthase.,  64  (11.0): [PMID:34044539] [10.1021/acs.jmedchem.1c00398]

Source

Source(1):

• Scientific Literature