3-Hydroxy-2-(2-mercaptopyrimidin-4-yl)-4-methyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

ID: ALA3734914

PubChem CID: 135882606

Max Phase: Preclinical

Molecular Formula: C18H16N2O3S

Molecular Weight: 340.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)c(-c2ccnc(S)n2)cc2c3c(c(=O)oc12)CCCC3

Standard InChI:  InChI=1S/C18H16N2O3S/c1-9-15(21)13(14-6-7-19-18(24)20-14)8-12-10-4-2-3-5-11(10)17(22)23-16(9)12/h6-8,21H,2-5H2,1H3,(H,19,20,24)

Standard InChI Key:  GOWBARZZAUQNNX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    1.7503   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558   -2.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    0.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7896   -2.1497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1368   -3.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3115    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0345    0.0592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7151    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6713    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482    3.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2683    2.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3675    0.2764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -2.1497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  9 10  1  0
  1 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 14  1  0
  3 11  1  0
  1 15  2  0
  8 16  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 17 23  1  0
  6 19  1  0
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3734914

   ---

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: 340.40

Molecular Weight (Monoisotopic): 340.0882

AlogP: 3.43

#Rotatable Bonds: 1

Polar Surface Area: 76.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.65

CX Basic pKa: 0.73

CX LogP: 4.00

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: -0.21

References

1. Galayev O, Garazd Y, Garazd M, Lesyk R..  (2015)  Synthesis and anticancer activity of 6-heteroarylcoumarins.,  105  [PMID:26491980] [10.1016/j.ejmech.2015.10.021]

Source

Source(1):

• Scientific Literature