Phytochemical Database for Neurological Disease

Phytochemical Name : alpha-Methyl-n-butylshikonin

Pubchem CID : 139246677

Molecular formula: C21H28O5

Molecular weight : 360.400

Canonical SMILES : CCCCC1(C(C(=O)C2=C(C=CC(=C2C1=O)O)O)C)C(CC=C(C)C)O

Synonymes : alpha-methyl-n-butylshikonin

Structure
3D structure	2D structure

MOL

SMILES

Predicted properties (NCBI Pubchem)

Physicochemical Properties

Formula : C21H28O5

Molecular weight (g/mol) : 360.400

Num. heavy atoms : 26

Num. arom. heavy atoms : 6

Fraction Csp3 : 0.520

Num. rotatable bonds : 6

Num. H-bond acceptors : 5

Num. H-bond donors : 3

Molar Refractivity : 102.070

Plasma TPSA : 94.830

Lipophilicity

Log P_o/w (iLOGP) : 3.610

Log P_o/w (XLOGP3) : 5.260

Log P_o/w (WLOGP) : 4.010

Log P_o/w (MLOGP) : 1.670

Log P_o/w (SILICOS-IT) : 4.340

Consensus Log P_o/w : 3.780

Water Solubility

Log S (ESOL) : -5.160

Solubility : 2.47E-03 mg/ml; 6.87E-06 mol/l

Class : Moderately soluble

Log S (Ali) : -7.000

Solubility : 3.60E-05 mg/ml; 9.98E-08 mol/l

Class : Poorly soluble

Log S (SILICOS-IT) : -4.580

Solubility : 9.55E-03 mg/ml; 2.65E-05 mol/l

Class : Moderately soluble

Pharmacokinetics

Absorption Intestinal absorption (human) : 73.918

BBB permeant : -0.772

P-gp substrate : No

Metabolism CYP2D6 substrate : No

Metabolism CYP3A4 substrate : Yes

CYP1A2 inhibitor : No

CYP2C19 inhibitor : No

CYP2C9 inhibitor : No

CYP2D6 inhibitor : No

CYP3A4 inhibitor : Yes

Log Kp (skin permeation) : -2.996

Druglikeness

Bioavailability Score : 0.550

Phytochemical classification

Kingdom : Organic compounds

Superclass : Benzenoids

Class : Naphthalenes

Subclass : Naphthoquinones

Parent Level 1 : Naphthoquinones