3-{4-[bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]phenyl}-1-(3-methoxyphenyl)thiourea

ID: ALA5282285

Max Phase: Preclinical

Molecular Formula: C33H24N2O7S

Molecular Weight: 592.63

Names and Identifiers

Canonical SMILES:  COc1cccc(NC(=S)Nc2ccc(C(c3c(O)c4ccccc4oc3=O)c3c(O)c4ccccc4oc3=O)cc2)c1

Standard InChI:  InChI=1S/C33H24N2O7S/c1-40-21-8-6-7-20(17-21)35-33(43)34-19-15-13-18(14-16-19)26(27-29(36)22-9-2-4-11-24(22)41-31(27)38)28-30(37)23-10-3-5-12-25(23)42-32(28)39/h2-17,26,36-37H,1H3,(H2,34,35,43)

Standard InChI Key:  OTVBQJIKQCZPIP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
   -3.8010    3.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864    3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745    3.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745    2.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846    2.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010    2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    3.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452    3.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9452    2.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    2.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306    3.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531    2.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    3.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    3.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3715    3.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3715    2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    2.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992    3.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    3.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010    2.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    2.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    3.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570    1.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531    1.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6614    0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606    0.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -0.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708    0.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    1.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -1.1072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -1.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7687   -2.3450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -1.1072    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -2.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1982   -2.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103   -2.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000   -3.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834   -3.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -2.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -1.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  8 11  2  0
  9 12  1  0
 13 14  1  0
 15 13  1  0
 16 15  2  0
 17 16  1  0
 14 18  1  0
 18 17  2  0
 12 18  1  0
 19 20  2  0
 15 20  1  0
 21 19  1  0
 22 21  2  0
 16 22  1  0
 14 23  2  0
 17 24  1  0
 12 25  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
 25 30  1  0
 10 31  1  0
 28 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 34 36  1  0
 37 36  2  0
 38 37  1  0
 39 38  2  0
 40 39  1  0
 41 40  2  0
 36 41  1  0
 38 42  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282285

   ---

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: 592.63

Molecular Weight (Monoisotopic): 592.1304

AlogP: 6.31

#Rotatable Bonds: 6

Polar Surface Area: 134.17

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.98

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 1.27

Aromatic Rings: 6

Heavy Atoms: 43

QED Weighted: 0.13

Np Likeness Score: -0.56

References

1. Faisal M, Saeed A, Shahzad D, Fattah TA, Lal B, Channar PA, Mahar J, Saeed S, Mahesar PA, Larik FA..  (2017)  Enzyme inhibitory activities an insight into the structure-Activity relationship of biscoumarin derivatives.,  141  [PMID:29032032] [10.1016/j.ejmech.2017.10.009]

Source

Source(1):

• Scientific Literature