IMPPAT Phytochemical information: 
Oroxylin A
Oroxylin A
Summary

SMILES: COc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccccc1
InChI: InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3
InChIKey: LKOJGSWUMISDOF-UHFFFAOYSA-N
DeepSMILES: COccO)cccc6O))c=O)cco6)cccccc6
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cOC; cO; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: O-methylated flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
oroxylin-a, 6-methylether of baicalein, oroxylin a, Oroxylin A, oroxylin, Oroxylin
External chemical identifiers:
CID:CID_5320315; ChEMBL:CHEMBL183513; ChEBI:CHEBI:61668; ZINC:ZINC000005998558; FDASRS:53K24Z586G; SureChEMBL:SCHEMBL431423; MolPort-019-937-219
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Oroxylin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.27
Log P RDKit 2.88
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
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 1
Shape complexity RDKit 0.06
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
Oroxylin A
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.76
Oroxylin A
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 -5.56
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Oroxylin A
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000372191SIRT3800
ENSP00000356022SOD2800
ENSP00000355759PARP1700
ENSP00000337459NOS1786
ENSP00000290573HK2800
ENSP00000263025MAPK3700
ENSP00000258743IL6800
ENSP00000225174PPIF800
ENSP00000215832MAPK1700
ENSP00000414303BDNF800
ENSP00000351273CASP8700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.