IMPPAT Phytochemical information: 
(8)-Shogaol

(8)-Shogaol
Summary

SMILES: CCCCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
InChI: InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+
InChIKey: LGZSMXJRMTYABD-MDZDMXLPSA-N
DeepSMILES: CCCCCCC/C=C/C=O)CCcccccc6)OC)))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: C/C=C/C(C)=O; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Methoxyphenols
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Aromatic polyketides
NP Classifier Class: Catechols with side chains
Synonymous chemical names:
cis-8-shogaol, trans-8-shogaol
External chemical identifiers:
CID:CID_6442560; ChEMBL:CHEMBL25893; ChEBI:CHEBI:174643; ZINC:ZINC000038143761; FDASRS:AV4IK2HCNT; SureChEMBL:SCHEMBL4886648; MolPort-001-741-448
Chemical structure download


(8)-Shogaol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 304.43
Log P RDKit 4.82
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


(8)-Shogaol
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 Bad
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47


(8)-Shogaol
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.55
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No