IMPPAT Phytochemical information: 
Piperbetol

Piperbetol
Summary

SMILES: C=CC[C@]12C=C(OC)C(=O)[C@@H]([C@@H]2OC(=O)C)[C@H]([C@@H]1C)c1ccc(c(c1)OC)O
InChI: InChI=1S/C22H26O6/c1-6-9-22-11-17(27-5)20(25)19(21(22)28-13(3)23)18(12(22)2)14-7-8-15(24)16(10-14)26-4/h6-8,10-12,18-19,21,24H,1,9H2,2-5H3/t12-,18+,19-,21-,22-/m0/s1
InChIKey: ZCLWBGXLYWCXHJ-OEYDJLRNSA-N
DeepSMILES: C=CC[C@@]C=COC))C=O)[C@@H][C@@H]6OC=O)C))))[C@H][C@@H]7C))cccccc6)OC)))O
Scaffold Graph/Node/Bond level: O=C1C=CC2CC1C(c1ccccc1)C2
Scaffold Graph/Node level: OC1CCC2CC1C(C1CCCCC1)C2
Scaffold Graph level: CC1CCC2CC1C(C1CCCCC1)C2
Functional groups: C=CC; COC(=CC)C(=O)C; CC(=O)OC; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Methoxyphenols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
piperbetol
External chemical identifiers:
CID:CID_10385474; ChEMBL:CHEMBL519704; ZINC:ZINC000038557831
Chemical structure download


Piperbetol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.44
Log P RDKit 3.36
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Piperbetol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6


Piperbetol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No