5-(6-chloro-5-(2-chloro-5-(4-(methylamino)pyrimidin-2-ylamino)benzo[b]thiophen-3-yl)pyridin-3-yl)-3,6-dimethylpyrimidin-4(3H)-one

ID: ALA4534250

PubChem CID: 155546745

Max Phase: Preclinical

Molecular Formula: C24H19Cl2N7OS

Molecular Weight: 524.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1ccnc(Nc2ccc3sc(Cl)c(-c4cc(-c5c(C)ncn(C)c5=O)cnc4Cl)c3c2)n1

Standard InChI:  InChI=1S/C24H19Cl2N7OS/c1-12-19(23(34)33(3)11-30-12)13-8-16(21(25)29-10-13)20-15-9-14(4-5-17(15)35-22(20)26)31-24-28-7-6-18(27-2)32-24/h4-11H,1-3H3,(H2,27,28,31,32)

Standard InChI Key:  ZYIUYTWUXIBOEY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.0121  -25.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7278  -25.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7250  -24.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0104  -24.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4422  -25.9469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1552  -25.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8661  -25.9451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5787  -25.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5779  -24.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8586  -24.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1489  -24.7117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8543  -23.4728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5659  -23.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2957  -25.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2994  -24.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5157  -24.4544    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0277  -25.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5097  -25.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -25.1160    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.2529  -26.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4448  -26.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1864  -27.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7353  -28.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5458  -27.9639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8003  -27.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6068  -27.0124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3786  -27.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8297  -27.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218  -27.2382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7629  -28.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3118  -28.6374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1197  -28.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4729  -26.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0885  -26.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6686  -29.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 15  1  0
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 17 19  1  0
 20 21  2  0
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 18 20  1  0
 25 26  1  0
 22 27  1  0
 27 28  1  0
 27 32  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 29 33  1  0
 28 34  2  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534250

   ---

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: 524.44

Molecular Weight (Monoisotopic): 523.0749

AlogP: 5.91

#Rotatable Bonds: 5

Polar Surface Area: 97.62

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.25

CX Basic pKa: 5.37

CX LogP: 4.70

CX LogD: 4.69

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: -1.14

References

1. Chen C, Zhu H, Stauffer F, Caravatti G, Vollmer S, Machauer R, Holzer P, Möbitz H, Scheufler C, Klumpp M, Tiedt R, Beyer KS, Calkins K, Guthy D, Kiffe M, Zhang J, Gaul C..  (2016)  Discovery of Novel Dot1L Inhibitors through a Structure-Based Fragmentation Approach.,  7  (8): [PMID:27563395] [10.1021/acsmedchemlett.6b00167]

2. Talukdar A, Mukherjee A, Bhattacharya D..  (2022)  Fascinating Transformation of SAM-Competitive Protein Methyltransferase Inhibitors from Nucleoside Analogues to Non-Nucleoside Analogues.,  65  (3.0): [PMID:35014841] [10.1021/acs.jmedchem.1c01208]

Source

Source(1):

• Scientific Literature