IMPPAT Phytochemical information: 
Ehretianone

Ehretianone
Summary

SMILES: CC(=CC[C@@]12C(=O)C=CC(=O)[C@@]32CC(=C[C@H]1c1cc(O)ccc1O3)C)C
InChI: InChI=1S/C22H22O4/c1-13(2)8-9-21-17-10-14(3)12-22(21,20(25)7-6-19(21)24)26-18-5-4-15(23)11-16(17)18/h4-8,10-11,17,23H,9,12H2,1-3H3/t17-,21-,22+/m0/s1
InChIKey: HBDVLYQTRSOPRO-BULFRSBZSA-N
DeepSMILES: CC=CC[C@]C=O)C=CC=O)[C@]6CC=C[C@H]%10cccO)ccc6O%12)))))))))C)))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)C23CC=CC(c4ccccc4O2)C13
Scaffold Graph/Node level: OC1CCC(O)C23CCCC(C4CCCCC4O2)C13
Scaffold Graph level: CC1CCC(C)C23CCCC(C4CCCCC4C2)C13
Functional groups: CC=C(C)C; O=C1C=CC(=O)CC1; CC(C)=CC; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Miscellaneous meroterpenoids
Synonymous chemical names:
ehretianone
External chemical identifiers:
CID:CID_10405602; ChEMBL:CHEMBL518366; ChEBI:CHEBI:65821; ZINC:ZINC000005767710
Chemical structure download


Ehretianone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 350.41
Log P RDKit 4.01
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4


Ehretianone
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.82


Ehretianone
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 -6.04
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No