Table 1 In silico ADME analysis of phytochemicals tested

Physicochemical properties

1.

SMILE

Cc1ccc(c(c1)O)C(C)C

CC(c1ccc(c(c1)O)C)C

O=CC=Cc1ccccc1

2.

Formula

C10H14O

C10H14O

C9H8O

3.

Molecular weight (g/mol)

150.22

150.22

132.16

4.

Number of heavy atoms

11

11

10

5.

Number of aromatic heavy atoms

6

6

6

6.

Fraction Csp3

0.40

0.40

0.00

7.

Number of rotatable bonds

1

1

2

8.

Number of H-bond acceptors

1

1

1

9.

Number of H-bond donors

1

1

0

10.

Molar refractivity

48.01

48.01

41.54

11.

Topological polar surface area (Ų)

20.23

20.23

17.07

Lipophilicity

12.

Log P_o/w (iLOGP)

2.32

2.24

1.65

13.

Log P_o/w (XLOGP3)

3.30

3.49

1.90

14.

Log P_o/w (WLOGP)

2.82

2.82

1.79

15.

Log P_o/w (MLOGP)

2.76

2.76

2.01

16.

Log P_o/w (SILICOS-IT)

2.79

2.79

2.48

17.

Consensus log P_o/w

2.80

2.82

1.97

Water solubility

18.

Log S (ESOL)

− 3.19

− 3.31

− 2.17

19.

Solubility

9.74e−02 mg/ml;

6.49e−04 mol/l

7.40e−02 mg/ml;

4.92e-04 mol/l

8.97e−01 mg/ml;

6.79e−03 mol/l

20.

Class

Soluble

Soluble

Soluble

21.

Log S (Ali)

− 3.40

− 3.60

− 1.88

22.

Solubility

5.97e−02 mg/ml;

3.98e−04 mol/l

3.79e−02 mg/ml;

2.53e−04 mol/l

1.74e + 00 mg/ml;

1.31e−02 mol/l

23.

Class

Soluble

Soluble

Very soluble

24.

Log S (SILICOS-IT)

− 3.01

− 3.01

− 2.40

25.

Solubility

1.46e-01 mg/ml;

9.71e−04 mol/l

1.46e−01 mg/ml;

9.71e−04 mol/l

5.26e−01 mg/ml;

3.98e−03 mol/l

26.

Class

Soluble

Soluble

Soluble

Pharmacokinetics

27.

GI absorption

High

High

High

28.

BBB permeant

Yes

Yes

Yes

29.

P-gp substrate

No

No

No

30.

CYP1A2 inhibitor

Yes

Yes

No

31.

CYP2C19 inhibitor

No

No

No

32.

CYP2C9 inhibitor

No

No

No

33.

CYP2D6 inhibitor

No

No

No

34.

CYP3A4 inhibitor

No

No

No

35.

Log K_p (skin permeation) (cm/s)

− 4.87

− 4.74

− 5.76

Drug-likeness

36.

Lipinski

Yes; 0 violation

Yes; 0 violation

Yes; 0 violation

37.

Ghose

No; 1 violation: MW < 160

No; 1 violation:

MW < 160

No; 2 violations: MW < 160, #atoms < 20

38.

Veber

Yes

Yes

Yes

39.

Egan

Yes

Yes

Yes

40.

Muegge

No; 2 violations: MW < 200, Heteroatoms < 2

No; 2 violations:

MW < 200,

Heteroatoms < 2

No; 2 violations: MW < 200, Heteroatoms < 2

41.

Bioavailability score

0.55

0.55

0.55

Medicinal chemistry

42.

PAINS

0 Alert

0 Alert

0 Alert

43.

Brenk

0 Alert

0 Alert

2 Alerts: aldehyde, michael_acceptor_1

44.

Lead likeness

No; 1 violation: MW < 250

No; 1 violation:

MW < 250

No; 1 violation: MW < 250

45.

Synthetic accessibility

1.00

1.00

1.65