IMPPAT Phytochemical information: 
Dicaffeyltartaric acid
Dicaffeyltartaric acid
Summary

SMILES: OC(=O)C(C(C(=O)O)(C/C=C/c1ccc(c(c1)O)O)O)(C/C=C/c1ccc(c(c1)O)O)O
InChI: InChI=1S/C22H22O10/c23-15-7-5-13(11-17(15)25)3-1-9-21(31,19(27)28)22(32,20(29)30)10-2-4-14-6-8-16(24)18(26)12-14/h1-8,11-12,23-26,31-32H,9-10H2,(H,27,28)(H,29,30)/b3-1+,4-2+
InChIKey: PWORHPPYXQRUEI-ZPUQHVIOSA-N
DeepSMILES: OC=O)CCC=O)O))C/C=C/cccccc6)O))O))))))))O))C/C=C/cccccc6)O))O))))))))O
Scaffold Graph/Node/Bond level: C(=Cc1ccccc1)CCCCC=Cc1ccccc1
Scaffold Graph/Node level: C(CCCCC1CCCCC1)CCCC1CCCCC1
Scaffold Graph level: C(CCCCC1CCCCC1)CCCC1CCCCC1
Functional groups: CC(=O)O; c/C=C/C; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Hydroxy acids and derivatives
ClassyFire Subclass: Medium-chain hydroxy acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
dicaffeyltartaric acid
External chemical identifiers:
CID:CID_129667515
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Dicaffeyltartaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.41
Log P RDKit 1.65
Topological polar surface area (Å2) RDKit 195.98
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Dicaffeyltartaric acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.262215
Dicaffeyltartaric 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 -7.93
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 Yes