IMPPAT Phytochemical information: 
Piperol A

Piperol A
Summary

SMILES: C=CC[C@@]12C[C@H]([C@H]([C@@H]2O)C(=O)C(=C1)OC)c1ccc(c(c1)OC)OC
InChI: InChI=1S/C20H24O5/c1-5-8-20-10-13(12-6-7-14(23-2)15(9-12)24-3)17(19(20)22)18(21)16(11-20)25-4/h5-7,9,11,13,17,19,22H,1,8,10H2,2-4H3/t13-,17-,19-,20+/m0/s1
InChIKey: MDBRPWOYUFAZSN-SOUCHZLYSA-N
DeepSMILES: C=CC[C@]C[C@H][C@H][C@@H]5O))C=O)C=C7)OC)))))cccccc6)OC)))OC
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; CO; COC(=CC)C(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Methoxybenzenes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Neolignans
Synonymous chemical names:
piperol a
External chemical identifiers:
CID:CID_102586046; ZINC:ZINC000238736005
Chemical structure download


Piperol A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.41
Log P RDKit 2.84
Topological polar surface area (Å2) RDKit 64.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 6
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


Piperol A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.804092


Piperol A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No