IMPPAT Phytochemical information: 
4,5-Di-O-caffeoylquinic acid
4,5-Di-O-caffeoylquinic acid
Summary

SMILES: O=C(O[C@H]1[C@H](O)C[C@](C[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)(O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChIKey: UFCLZKMFXSILNL-RVXRWRFUSA-N
DeepSMILES: O=CO[C@H][C@H]O)C[C@]C[C@H]6OC=O)/C=C/cccccc6)O))O)))))))))))O)C=O)O)))))))/C=C/cccccc6)O))O
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: 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:
4,5-dicaffeoylquinic acid, 4,5-di-o-caffeoylquinic acid
External chemical identifiers:
CID:CID_6474309; ChEMBL:CHEMBL177126; ChEBI:CHEBI:141136; ZINC:ZINC000013556374; FDASRS:E57A0DKE0B; SureChEMBL:SCHEMBL18317176; MolPort-001-740-223
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
4,5-Di-O-caffeoylquinic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 516.46
Log P RDKit 1.03
Topological polar surface area (Å2) RDKit 211.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 9
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
4,5-Di-O-caffeoylquinic acid
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.15621
4,5-Di-O-caffeoylquinic 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 -8.37
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
4,5-Di-O-caffeoylquinic acid
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000311032CASP3700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.