IMPPAT Phytochemical information: 
Prunin 3'',6''-di-p-coumarate
Prunin 3'',6''-di-p-coumarate
Summary

SMILES: O=C(OCC1O[C@@H](Oc2cc(O)c3c(c2)OC(CC3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)OC(=O)/C=C/c1ccc(cc1)O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C39H34O14/c40-24-9-1-21(2-10-24)5-15-33(45)49-20-32-36(47)38(53-34(46)16-6-22-3-11-25(41)12-4-22)37(48)39(52-32)50-27-17-28(43)35-29(44)19-30(51-31(35)18-27)23-7-13-26(42)14-8-23/h1-18,30,32,36-43,47-48H,19-20H2/b15-5+,16-6+/t30?,32?,36-,37?,38+,39-/m1/s1
InChIKey: YHSNRKOEKHUGSK-VFHDUFKDSA-N
DeepSMILES: O=COCCO[C@@H]OcccO)ccc6)OCCC6=O)))cccccc6))O)))))))))))))C[C@H][C@@H]6O))OC=O)/C=C/cccccc6))O))))))))))O)))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CC(OC(=O)C=Cc2ccccc2)CC(Oc2ccc3c(c2)OC(c2ccccc2)CC3=O)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CC(OC(O)CCC2CCCCC2)CC(OC2CCC3C(O)CC(C4CCCCC4)OC3C2)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CC(CC(C)CCC2CCCCC2)CC(CC2CCC3C(C)CC(C4CCCCC4)CC3C2)C1
Functional groups: c/C=C/C(=O)OC; cO[C@@H](C)OC; cO; cOC; cC(=O)C; CO
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: Flavanones
Synonymous chemical names:
prunin-3��,6��-di-p-coumarate
External chemical identifiers:
CID:CID_42607911
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Prunin 3'',6''-di-p-coumarate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 726.69
Log P RDKit 3.92
Topological polar surface area (Å2) RDKit 218.74
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 53
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 31
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
Prunin 3'',6''-di-p-coumarate
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.100859
Prunin 3'',6''-di-p-coumarate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes