IMPPAT Phytochemical information: 
3-O-caffeoyl-4-o-sinapoylquinic acid
3-O-caffeoyl-4-o-sinapoylquinic acid
Summary

SMILES: COc1cc(/C=C/C(=O)OC2C(O)C[C@@](C[C@H]2OC(=O)/C=C/c2ccc(c(c2)O)O)(O)C(=O)O)cc(c1O)OC
InChI: InChI=1S/C27H28O13/c1-37-19-10-15(11-20(38-2)24(19)33)5-8-23(32)40-25-18(30)12-27(36,26(34)35)13-21(25)39-22(31)7-4-14-3-6-16(28)17(29)9-14/h3-11,18,21,25,28-30,33,36H,12-13H2,1-2H3,(H,34,35)/b7-4+,8-5+/t18?,21-,25?,27+/m1/s1
InChIKey: BEDSGEULUAVXQH-QLTBITECSA-N
DeepSMILES: COccc/C=C/C=O)OCCO)C[C@@]C[C@H]6OC=O)/C=C/cccccc6)O))O)))))))))))O)C=O)O))))))))))ccc6O))OC
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCCC1OC(=O)C=Cc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCCC1OC(O)CCC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1CC(C)CCC1CCCCC1
Functional groups: cOC; c/C=C/C(=O)OC; CO; cO; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Alcohols and polyols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
3-o-caffeoyl-4-o-sinapoylquinic acid, 3-O-caffeoyl-4-O-sinapoylquinic acid
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-O-caffeoyl-4-o-sinapoylquinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 560.51
Log P RDKit 1.34
Topological polar surface area (Å2) RDKit 209.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
3-O-caffeoyl-4-o-sinapoylquinic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
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 0.15
3-O-caffeoyl-4-o-sinapoylquinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -8.43
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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