IMPPAT Phytochemical information: 
Caffeoyltartronic acid

Caffeoyltartronic acid
Summary

SMILES: OC(=O)C(C(=O)/C=C/c1ccc(c(c1)O)O)(C(=O)O)O
InChI: InChI=1S/C12H10O8/c13-7-3-1-6(5-8(7)14)2-4-9(15)12(20,10(16)17)11(18)19/h1-5,13-14,20H,(H,16,17)(H,18,19)/b4-2+
InChIKey: YVUYIEJFBANVBK-DUXPYHPUSA-N
DeepSMILES: OC=O)CC=O)/C=C/cccccc6)O))O))))))))C=O)O))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC(=O)O; c/C=C/C(C)=O; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
caffeoyltartronic acid
External chemical identifiers:
CID:CID_129660911
Chemical structure download


Caffeoyltartronic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 282.2
Log P RDKit -0.42
Topological polar surface area (Å2) RDKit 152.36
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.08
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
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 1


Caffeoyltartronic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.277131


Caffeoyltartronic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.99
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 No