4-(dimethylamino)-1-(6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-yl)-N-(3-(thiophen-2-yl)phenyl)piperidine-4-carboxamide

ID: ALA3800357

PubChem CID: 127045877

Max Phase: Preclinical

Molecular Formula: C28H32N6OS

Molecular Weight: 500.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)C1(C(=O)Nc2cccc(-c3cccs3)c2)CCN(c2ncnc3[nH]c4c(c23)CCCC4)CC1

Standard InChI:  InChI=1S/C28H32N6OS/c1-33(2)28(27(35)31-20-8-5-7-19(17-20)23-11-6-16-36-23)12-14-34(15-13-28)26-24-21-9-3-4-10-22(21)32-25(24)29-18-30-26/h5-8,11,16-18H,3-4,9-10,12-15H2,1-2H3,(H,31,35)(H,29,30,32)

Standard InChI Key:  YZEBEKHXMANRDT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5059    3.0395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2127    3.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    6.7382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    6.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6428    9.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3510    8.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8449    7.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2701    6.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    4.5861    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    4.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6305    5.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6145    6.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4  1  1  0
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  7 25  1  0
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  4  8  1  0
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  8 13  1  0
  9 10  1  0
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 11 12  1  0
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 11 15  1  0
 15 16  2  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 24 25  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 14 30  1  0
 14 31  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 32  2  0
 20 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800357

   ---

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: 500.67

Molecular Weight (Monoisotopic): 500.2358

AlogP: 5.10

#Rotatable Bonds: 5

Polar Surface Area: 77.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.04

CX Basic pKa: 7.83

CX LogP: 5.03

CX LogD: 4.44

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.40

Np Likeness Score: -1.49

References

1. Alen J, Bourin A, Boland S, Geraets J, Schroeders P, Defert O.  (2016)  Tetrahydro-pyrimido-indoles as selective LIMK inhibitors: synthesis, selectivity profiling and structureactivity studies,  7  (3): [10.1039/C5MD00473J]

Source

Source(1):

• Scientific Literature