IMPPAT Phytochemical information: 
5,7-dihydroxy-2-[4-hydroxy-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
5,7-dihydroxy-2-[4-hydroxy-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Summary

SMILES: OCC1O[C@@H](Oc2cc(ccc2O)c2cc(=O)c3c(o2)cc(cc3O)O)C([C@H]([C@H]1O)O)O
InChI: InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-14-3-8(1-2-10(14)24)13-6-12(26)17-11(25)4-9(23)5-15(17)30-13/h1-6,16,18-25,27-29H,7H2/t16?,18-,19-,20?,21+/m0/s1
InChIKey: VNTMXJLNIJFLIF-BVPMPBNFSA-N
DeepSMILES: OCCO[C@@H]Occcccc6O))))ccc=O)cco6)cccc6O)))O))))))))))))C[C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2cccc(OC3CCCCO3)c2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCC(OC3CCCCO3)C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC(CC3CCCCC3)C2)CC2CCCCC12
Functional groups: CO; cO[C@@H](C)OC; cO; 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:
luteolin-3'-glucoside, 3'-glucoside of luteolin
External chemical identifiers:
CID:CID_44258073
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5,7-dihydroxy-2-[4-hydroxy-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.38
Log P RDKit -0.24
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
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
5,7-dihydroxy-2-[4-hydroxy-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.28
5,7-dihydroxy-2-[4-hydroxy-3-[(2S,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
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 -8.00
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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