IMPPAT Phytochemical information: 
1,3,5-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one

1,3,5-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
Summary

SMILES: CC(=CCc1c(O)cc2c(c1O)c(=O)c1c(o2)c(O)ccc1)C
InChI: InChI=1S/C18H16O5/c1-9(2)6-7-10-13(20)8-14-15(16(10)21)17(22)11-4-3-5-12(19)18(11)23-14/h3-6,8,19-21H,7H2,1-2H3
InChIKey: XEHWUYVZHDBZHK-UHFFFAOYSA-N
DeepSMILES: CC=CCccO)cccc6O))c=O)cco6)cO)ccc6))))))))))))))C
Scaffold Graph/Node/Bond level: O=c1c2ccccc2oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCCC21
Functional groups: CC=C(C)C; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Xanthones
NP Classifier Class: Plant xanthones
Synonymous chemical names:
2-(3-methylbut-2-enyl)-1,3,5-trihydroxyxanthone
External chemical identifiers:
CID:CID_9995643; ChEMBL:CHEMBL4203085; ZINC:ZINC000014819720
Chemical structure download


1,3,5-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 312.32
Log P RDKit 3.57
Topological polar surface area (Å2) RDKit 90.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
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 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


1,3,5-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
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 0.5


1,3,5-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
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 -5.10
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No