IMPPAT Phytochemical information: 
Isoaffinetin
Isoaffinetin
Summary

SMILES: OCC1O[C@H](C([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1cc(O)c(c(c1)O)O
InChI: InChI=1S/C21H20O12/c22-5-13-17(28)19(30)20(31)21(33-13)15-8(24)4-12-14(18(15)29)7(23)3-11(32-12)6-1-9(25)16(27)10(26)2-6/h1-4,13,17,19-22,24-31H,5H2/t13?,17-,19+,20?,21+/m1/s1
InChIKey: YVQAFWXBYGHQPW-BPIQGPLOSA-N
DeepSMILES: OCCO[C@H]C[C@H][C@@H]6O))O))O))ccO)cccc6O))c=O)cco6)cccO)ccc6)O))O
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; 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:
Isoaffinetin, isoaffinetin
External chemical identifiers:
CID:CID_44258239
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isoaffinetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 464.38
Log P RDKit -0.5
Topological polar surface area (Å2) RDKit 221.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 12
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 3
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
Isoaffinetin
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 1
Ghose rule RDKit Failed
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 0.22
Isoaffinetin
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 -9.49
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No