IMPPAT Phytochemical information: 
1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-, (R)-

1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-, (R)-
Summary

SMILES: COc1cc2C[C@@H](C)OC(=O)c2c(c1OC)O
InChI: InChI=1S/C12H14O5/c1-6-4-7-5-8(15-2)11(16-3)10(13)9(7)12(14)17-6/h5-6,13H,4H2,1-3H3/t6-/m1/s1
InChIKey: VXWBNPSAWLNEKD-ZCFIWIBFSA-N
DeepSMILES: COcccC[C@@H]C)OC=O)c6cc%10OC)))O
Scaffold Graph/Node/Bond level: O=C1OCCc2ccccc21
Scaffold Graph/Node level: OC1OCCC2CCCCC21
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cOC; cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 2-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
kigelin, Kigelin
External chemical identifiers:
CID:CID_22295076; ZINC:ZINC000013480554
Chemical structure download


1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-, (R)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 238.24
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 64.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-, (R)-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.791023


1H-2-Benzopyran-1-one, 3,4-dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-, (R)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.06
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No