3-(4-Amino-5-oxo-5H-chromeno[4,3-d]pyrimidin-2-yl)phenyl methanesulfonate

ID: ALA5289870

Max Phase: Preclinical

Molecular Formula: C18H13N3O5S

Molecular Weight: 383.39

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Oc1cccc(-c2nc(N)c3c(=O)oc4ccccc4c3n2)c1

Standard InChI:  InChI=1S/C18H13N3O5S/c1-27(23,24)26-11-6-4-5-10(9-11)17-20-15-12-7-2-3-8-13(12)25-18(22)14(15)16(19)21-17/h2-9H,1H3,(H2,19,20,21)

Standard InChI Key:  KKFLBSBSMGLFEA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.0639    0.6192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -0.6178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -1.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7785   -0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3628    1.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7905    1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921    0.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802    0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -1.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118   -0.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4991    0.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2260    1.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044    1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -1.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -1.8547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067    0.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213    0.6220    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    1.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    1.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  1  6  2  0
  6  5  1  0
  7  3  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
 11 10  1  0
  7 12  1  0
 12 11  2  0
  6 13  1  0
 14 13  1  0
 15 14  1  0
 16 15  2  0
  1 16  1  0
 15 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 16 20  1  0
 13 21  2  0
  5 22  1  0
 11 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289870

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.39

Molecular Weight (Monoisotopic): 383.0576

AlogP: 2.32

#Rotatable Bonds: 3

Polar Surface Area: 125.38

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.29

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.77

References

1. Lv N, Sun M, Liu C, Li J..  (2017)  Design and synthesis of 2-phenylpyrimidine coumarin derivatives as anticancer agents.,  27  (19): [PMID:28888820] [10.1016/j.bmcl.2017.08.044]

Source

Source(1):

• Scientific Literature