IMPPAT Phytochemical information: 
Pimentol
Pimentol
Summary

SMILES: C=CCc1cc(O[C@@H]2O[C@H](COC(=O)c3cc(O)c(c(c3)O)O)[C@H]([C@@H]([C@H]2O)O)O)c(c(c1)OC)O
InChI: InChI=1S/C23H26O12/c1-3-4-10-5-14(32-2)18(27)15(6-10)34-23-21(30)20(29)19(28)16(35-23)9-33-22(31)11-7-12(24)17(26)13(25)8-11/h3,5-8,16,19-21,23-30H,1,4,9H2,2H3/t16-,19-,20+,21-,23-/m1/s1
InChIKey: LFQREKVEOMIWQF-JTLUYSSBSA-N
DeepSMILES: C=CCcccO[C@@H]O[C@H]COC=O)cccO)ccc6)O))O))))))))[C@H][C@@H][C@H]6O))O))O))))))ccc6)OC)))O
Scaffold Graph/Node/Bond level: O=C(OCC1CCCC(Oc2ccccc2)O1)c1ccccc1
Scaffold Graph/Node level: OC(OCC1CCCC(OC2CCCCC2)O1)C1CCCCC1
Scaffold Graph level: CC(CCC1CCCC(CC2CCCCC2)C1)C1CCCCC1
Functional groups: cOC; C=CC; cO; cO[C@@H](C)OC; cC(=O)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
pimentol
External chemical identifiers:
CID:CID_9917512; ChEMBL:CHEMBL498040; ChEBI:CHEBI:175810; ZINC:ZINC000034027235; FDASRS:3U53LNA6A3; MolPort-046-153-815
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pimentol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 494.45
Log P RDKit 0.29
Topological polar surface area (Å2) RDKit 195.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Pimentol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.15
Pimentol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.56
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes