1-(6,7-Dichloro-9b-(4,6-difluoro-1H-indol-3-yl)-1,3,4,9b-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)-2-hydroxyethan-1-one

ID: ALA5093281

PubChem CID: 166633056

Max Phase: Preclinical

Molecular Formula: C21H15Cl2F2N3O2

Molecular Weight: 450.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CO)N1CCC2=Nc3c(ccc(Cl)c3Cl)C2(c2c[nH]c3cc(F)cc(F)c23)C1

Standard InChI:  InChI=1S/C21H15Cl2F2N3O2/c22-13-2-1-11-20(19(13)23)27-16-3-4-28(17(30)8-29)9-21(11,16)12-7-26-15-6-10(24)5-14(25)18(12)15/h1-2,5-7,26,29H,3-4,8-9H2

Standard InChI Key:  YQPHVKHOHUERKY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.3965  -18.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113  -19.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501  -19.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2202  -18.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632  -19.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793  -19.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751  -20.6244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563  -19.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641  -20.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0804  -20.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7935  -20.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7817  -19.5151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649  -19.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916  -19.0330    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7681  -20.5413    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4928  -19.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2101  -19.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4867  -18.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9214  -19.0891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506  -18.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241  -17.4332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6758  -18.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497  -17.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0097  -18.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8130  -18.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570  -17.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0965  -16.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938  -16.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6437  -16.3582    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0704  -19.0408    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
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  8  5  1  0
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  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  2 14  1  0
  3 15  1  0
 12 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
  8 20  1  0
 20 24  1  0
 23 21  1  0
 21 22  1  0
 22 20  2  0
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 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 27 29  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5093281

   ---

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: 450.27

Molecular Weight (Monoisotopic): 449.0509

AlogP: 4.35

#Rotatable Bonds: 2

Polar Surface Area: 68.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.62

CX Basic pKa: 3.35

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.61

Np Likeness Score: -0.52

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