6-(3-Methoxyphenyl)-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]-pyrimidin-4-amine

ID: ALA4520163

PubChem CID: 155542244

Max Phase: Preclinical

Molecular Formula: C22H21N3O4S

Molecular Weight: 423.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2cc3ncnc(Nc4cc(OC)c(OC)c(OC)c4)c3s2)c1

Standard InChI:  InChI=1S/C22H21N3O4S/c1-26-15-7-5-6-13(8-15)19-11-16-21(30-19)22(24-12-23-16)25-14-9-17(27-2)20(29-4)18(10-14)28-3/h5-12H,1-4H3,(H,23,24,25)

Standard InChI Key:  GFEZIYFTLOBGJY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.9071  -18.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9043  -17.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1957  -16.9544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4894  -18.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4861  -17.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7085  -17.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2312  -17.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7139  -18.4381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.1972  -19.4089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9049  -19.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9005  -20.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6073  -21.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3161  -20.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3137  -19.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6063  -19.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6067  -21.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3141  -22.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0242  -21.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7315  -20.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0200  -19.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0173  -18.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4186  -17.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0077  -17.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1913  -17.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7847  -17.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2006  -18.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0157  -18.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7801  -16.3727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9629  -16.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
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 17 18  1  0
 14 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  8 23  1  0
 25 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520163

   ---

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: 423.49

Molecular Weight (Monoisotopic): 423.1253

AlogP: 5.14

#Rotatable Bonds: 7

Polar Surface Area: 74.73

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.93

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -1.06

References

1. Romagnoli R, Prencipe F, Oliva P, Baraldi S, Baraldi PG, Schiaffino Ortega S, Chayah M, Kimatrai Salvador M, Lopez-Cara LC, Brancale A, Ferla S, Hamel E, Ronca R, Bortolozzi R, Mariotto E, Mattiuzzo E, Viola G..  (2019)  Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors.,  62  (3): [PMID:30633509] [10.1021/acs.jmedchem.8b01391]

Source

Source(1):

• Scientific Literature