IMPPAT Phytochemical information: 
(2S)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one

(2S)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one
Summary

SMILES: COc1cc2O[C@@H](CC(=O)c2c(c1CC=C(C)C)O)c1cc(OC)c(c(c1)OC)OC
InChI: InChI=1S/C24H28O7/c1-13(2)7-8-15-18(27-3)12-19-22(23(15)26)16(25)11-17(31-19)14-9-20(28-4)24(30-6)21(10-14)29-5/h7,9-10,12,17,26H,8,11H2,1-6H3/t17-/m0/s1
InChIKey: ZRRIYQXQQBEZOK-KRWDZBQOSA-N
DeepSMILES: COcccO[C@@H]CC=O)c6cc%10CC=CC)C)))))O)))))cccOC))ccc6)OC)))OC
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cOC; cC(=O)C; CC=C(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
artoflavanone
External chemical identifiers:
CID:CID_90473423; ZINC:ZINC000014648306
Chemical structure download


(2S)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 428.48
Log P RDKit 4.64
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


(2S)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.64


(2S)-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrochromen-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No