IMPPAT Phytochemical information: 
Xanthoxylone
Xanthoxylone
Summary

SMILES: O=C1C[C@H]2C(C)(C)CCC[C@@]2([C@@H]2[C@]1(C)[C@]1(C)CC[C@@]3([C@H](C1=CC2)CC(CC3)(C)C)C)C
InChI: InChI=1S/C30H48O/c1-25(2)14-15-27(5)16-17-29(7)20(21(27)19-25)10-11-22-28(6)13-9-12-26(3,4)23(28)18-24(31)30(22,29)8/h10,21-23H,9,11-19H2,1-8H3/t21-,22+,23-,27+,28+,29+,30-/m0/s1
InChIKey: VTWIIFKLIYLLFG-KIPBKJNPSA-N
DeepSMILES: O=CC[C@H]CC)C)CCC[C@@]6[C@@H][C@]%10C)[C@]C)CC[C@@][C@H]C6=CC%10)))CCCC6))C)C))))C)))))))C
Scaffold Graph/Node/Bond level: O=C1CC2CCCCC2C2CC=C3C4CCCCC4CCC3C12
Scaffold Graph/Node level: OC1CC2CCCCC2C2CCC3C4CCCCC4CCC3C12
Scaffold Graph level: CC1CC2CCCCC2C2CCC3C4CCCCC4CCC3C12
Functional groups: CC(=O)C; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Multiflorane triterpenoids|Oleanane triterpenoids
Synonymous chemical names:
Xanthoxylone, xanthoxylone
External chemical identifiers:
CID:CID_102239690; ZINC:ZINC000238740456
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Xanthoxylone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.71
Log P RDKit 8.38
Topological polar surface area (Å2) RDKit 17.07
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Xanthoxylone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.356823
Xanthoxylone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -2.49
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 No
P-glycoprotein substrate SwissADME No