3-methyl-1-(5-(3-(2-(piperidin-1-yl)ethoxy)phenyl)-2-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-ylamino)-1H-pyrrole-2,5-dione hydrochloride

ID: ALA3290631

PubChem CID: 24896719

Max Phase: Preclinical

Molecular Formula: C28H28ClN5O3S2

Molecular Weight: 545.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)N(Nc2nc(-c3cccs3)nc3scc(-c4cccc(OCCN5CCCCC5)c4)c23)C1=O.Cl

Standard InChI:  InChI=1S/C28H27N5O3S2.ClH/c1-18-15-23(34)33(28(18)35)31-26-24-21(17-38-27(24)30-25(29-26)22-9-6-14-37-22)19-7-5-8-20(16-19)36-13-12-32-10-3-2-4-11-32;/h5-9,14-17H,2-4,10-13H2,1H3,(H,29,30,31);1H

Standard InChI Key:  SBXOZKDGWVQQCI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
   31.3503  -23.1903    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.6503  -24.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3667  -24.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3639  -23.2017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6486  -22.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9357  -24.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9369  -23.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1490  -22.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6607  -23.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1470  -24.2875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.6468  -21.9678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3603  -21.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1165  -21.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6672  -21.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2531  -20.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4467  -20.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8331  -20.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2887  -22.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4877  -21.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0827  -24.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1736  -25.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9823  -25.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3958  -24.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8425  -24.1078    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.8953  -22.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4487  -21.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1955  -20.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3882  -20.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8344  -21.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0905  -21.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0272  -21.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4764  -21.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6693  -21.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1186  -22.0988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3126  -21.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7628  -22.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0154  -23.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8231  -23.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3783  -22.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
 16 17  2  0
 13 18  2  0
 14 19  1  0
  3 20  1  0
 23 24  1  0
 21 22  1  0
 20 21  2  0
 22 23  2  0
 24 20  1  0
  8 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 39  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
M  END

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: 545.69

Molecular Weight (Monoisotopic): 545.1555

AlogP: 5.59

#Rotatable Bonds: 8

Polar Surface Area: 87.66

Molecular Species: BASE

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.94

CX Basic pKa: 8.94

CX LogP: 5.92

CX LogD: 4.38

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.29

Np Likeness Score: -1.50

References

1. Park CH, Lee C, Yang JS, Joe BY, Chun K, Kim H, Kim HY, Kang JS, Lee JI, Kim MH, Han G..  (2014)  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors.,  24  (12): [PMID:24813730] [10.1016/j.bmcl.2014.04.058]

Source

Source(1):

• Scientific Literature