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

ID: ALA5279003

Max Phase: Preclinical

Molecular Formula: C21H12BrN3O5S2

Molecular Weight: 530.38

Names and Identifiers

Canonical SMILES:  Nc1nc(-c2cccc(OS(=O)(=O)c3ccc(Br)s3)c2)nc2c1c(=O)oc1ccccc12

Standard InChI:  InChI=1S/C21H12BrN3O5S2/c22-15-8-9-16(31-15)32(27,28)30-12-5-3-4-11(10-12)20-24-18-13-6-1-2-7-14(13)29-21(26)17(18)19(23)25-20/h1-10H,(H2,23,24,25)

Standard InChI Key:  PHISVVUQNBAMBY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -2.8437    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1292    0.6192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173   -0.6177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274   -1.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437   -0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2771   -0.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    0.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697    1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913    1.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -1.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274   -1.8547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7026    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7252    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7268    0.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0149    0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4414    0.2095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1560    0.6221    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5694    1.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7442    1.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6241    0.5449    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1761   -0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637   -0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -0.0679    0.0000 Br  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
  6  5  1  0
  1  6  2  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
  1 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  9 14  1  0
  7 15  2  0
  5 16  1  0
 17  3  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 28 25  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 25  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279003

   ---

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: 530.38

Molecular Weight (Monoisotopic): 528.9402

AlogP: 4.58

#Rotatable Bonds: 4

Polar Surface Area: 125.38

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.29

CX LogP: 5.62

CX LogD: 5.62

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.20

Np Likeness Score: -1.24

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