IMPPAT Phytochemical information: 
[5-Acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate
[5-Acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate
Summary

SMILES: CC(=O)OC1C(O)C(O)C(OC1c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O)COC(=O)C
InChI: InChI=1S/C25H24O13/c1-9(26)35-8-18-21(32)23(34)25(36-10(2)27)24(38-18)20-15(31)7-17-19(22(20)33)14(30)6-16(37-17)11-3-4-12(28)13(29)5-11/h3-7,18,21,23-25,28-29,31-34H,8H2,1-2H3
InChIKey: JBEPAVBUODEETF-UHFFFAOYSA-N
DeepSMILES: CC=O)OCCO)CO)COC6ccO)cccc6O))c=O)cco6)cccccc6)O))O)))))))))))))))COC=O)C
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccc(C3CCCCO3)cc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCC(C3CCCCO3)CC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCC(C3CCCCC3)CC12
Functional groups: cO; COC(C)=O; CO; COC; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
"2"",6""-di-o-acetylisoorientin, 2'',6''-di-o-acetyl-iso-orientin"
External chemical identifiers:
CID:CID_14681454
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[5-Acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 532.45
Log P RDKit 0.94
Topological polar surface area (Å2) RDKit 213.42
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.32
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
[5-Acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.199561
[5-Acetyloxy-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-3,4-dihydroxyoxan-2-yl]methyl acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.23
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes