IMPPAT Phytochemical information: 
1,3,5-Tricaffeoylquinic acid
1,3,5-Tricaffeoylquinic acid
Summary

SMILES: O=C(O[C@@H]1CC(OC(=O)/C=C/c2ccc(c(c2)O)O)(C[C@H](C1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C34H30O15/c35-21-7-1-18(13-24(21)38)4-10-29(41)47-27-16-34(33(45)46,49-31(43)12-6-20-3-9-23(37)26(40)15-20)17-28(32(27)44)48-30(42)11-5-19-2-8-22(36)25(39)14-19/h1-15,27-28,32,35-40,44H,16-17H2,(H,45,46)/b10-4+,11-5+,12-6+/t27-,28-,32?,34?/m1/s1
InChIKey: MSKVJEAKVWAQTA-JFPZSYFPSA-N
DeepSMILES: O=CO[C@@H]CCOC=O)/C=C/cccccc6)O))O)))))))))C[C@H]C6O))OC=O)/C=C/cccccc6)O))O)))))))))))C=O)O))))))/C=C/cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CC(OC(=O)C=Cc2ccccc2)CC(OC(=O)C=Cc2ccccc2)C1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CC(OC(O)CCC2CCCCC2)CC(OC(O)CCC2CCCCC2)C1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CC(CC(C)CCC2CCCCC2)CC(CC(C)CCC2CCCCC2)C1
Functional groups: 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:
1,3,5-tri-o-caffeoylquinic acid
External chemical identifiers:
CID:CID_10190081
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1,3,5-Tricaffeoylquinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 678.6
Log P RDKit 2.71
Topological polar surface area (Å2) RDKit 257.81
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 28
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 13
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
1,3,5-Tricaffeoylquinic 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 3
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 0.07
1,3,5-Tricaffeoylquinic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.98
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