Phytochemical Database for Neurological Disease

Phytochemical Name : methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[hydroxy-(4-hydroxyphenyl)methyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

Pubchem CID : 10099943

Molecular formula: C28H30O14

Molecular weight : 590.500

Canonical SMILES : CC(=O)OCC1C(C(C(C(O1)OC2C3C(C=CC34C=C(C(=O)O4)C(C5=CC=C(C=C5)O)O)C(=CO2)C(=O)OC)O)O)O

Synonymes : Acetylgaertneroside

Structure
3D structure	2D structure

MOL

SMILES

Predicted properties (NCBI Pubchem)

Physicochemical Properties

Formula : C28H30O14

Molecular weight (g/mol) : 590.500

Num. heavy atoms : 42

Num. arom. heavy atoms : 6

Fraction Csp3 : 0.460

Num. rotatable bonds : 9

Num. H-bond acceptors : 14

Num. H-bond donors : 5

Molar Refractivity : 136.300

Plasma TPSA : 207.740

Lipophilicity

Log P_o/w (iLOGP) : 2.900

Log P_o/w (XLOGP3) : -0.240

Log P_o/w (WLOGP) : -1.070

Log P_o/w (MLOGP) : -1.090

Log P_o/w (SILICOS-IT) : -1.000

Consensus Log P_o/w : -0.100

Water Solubility

Log S (ESOL) : -2.860

Solubility : 8.12E-01 mg/ml; 1.37E-03 mol/l

Class : Soluble

Log S (Ali) : -3.660

Solubility : 1.28E-01 mg/ml; 2.16E-04 mol/l

Class : Soluble

Log S (SILICOS-IT) : -0.300

Solubility : 2.93E+02 mg/ml; 4.95E-01 mol/l

Class : Soluble

Pharmacokinetics

Absorption Intestinal absorption (human) : 51.298

BBB permeant : -1.771

P-gp substrate : Yes

Metabolism CYP2D6 substrate : No

Metabolism CYP3A4 substrate : Yes

CYP1A2 inhibitor : No

CYP2C19 inhibitor : No

CYP2C9 inhibitor : No

CYP2D6 inhibitor : No

CYP3A4 inhibitor : No

Log Kp (skin permeation) : -2.735

Druglikeness

Bioavailability Score : 0.110

Phytochemical classification

Kingdom : Organic compounds

Superclass : Lipids and lipid-like molecules

Class : Prenol lipids

Subclass : Terpene glycosides

Parent Level 1 : Iridoid O-glycosides