1-(2-(Pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ol

ID: ALA4648499

PubChem CID: 156020063

Max Phase: Preclinical

Molecular Formula: C20H22N4OS

Molecular Weight: 366.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC1CCN(c2nc(-c3ccncc3)nc3sc4c(c23)CCCC4)CC1

Standard InChI:  InChI=1S/C20H22N4OS/c25-14-7-11-24(12-8-14)19-17-15-3-1-2-4-16(15)26-20(17)23-18(22-19)13-5-9-21-10-6-13/h5-6,9-10,14,25H,1-4,7-8,11-12H2

Standard InChI Key:  QZNGAXLDYYNAHX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.0131  -17.6259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7228  -17.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7199  -16.3938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0113  -15.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3051  -17.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3063  -16.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5281  -17.4681    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491  -16.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5342  -16.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063  -15.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3922  -15.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071  -15.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360  -16.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0075  -15.1714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4276  -17.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4275  -18.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351  -18.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8431  -18.4392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8392  -17.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1311  -17.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7168  -14.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7150  -13.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072  -13.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2996  -13.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2997  -14.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0065  -12.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  7  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
  4 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  2 15  1  0
 14 21  1  0
 14 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4648499

   ---

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: 366.49

Molecular Weight (Monoisotopic): 366.1514

AlogP: 3.59

#Rotatable Bonds: 2

Polar Surface Area: 62.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.94

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.75

Np Likeness Score: -1.83

References

1. Liu X, Wilson MW, Liu K, Lee P, Yeomans L, Hagen SE, Lin CM, Wen B, Sun D, White AD, Showalter HD, Antonetti DA..  (2020)  Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidines as atypical protein kinase C inhibitors to control retinal vascular permeability and cytokine-induced edema.,  28  (11): [PMID:32327351] [10.1016/j.bmc.2020.115480]

Source

Source(1):

• Scientific Literature