IMPPAT Phytochemical information: 
5-Galloylshikimic acid
5-Galloylshikimic acid
Summary

SMILES: O[C@@H]1C=C(C[C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
InChI: InChI=1S/C14H14O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-3,9-10,12,15-19H,4H2,(H,20,21)/t9-,10-,12-/m1/s1
InChIKey: NTNQTAISNHFKRA-CKYFFXLPSA-N
DeepSMILES: O[C@@H]C=CC[C@H][C@@H]6O))OC=O)cccO)ccc6)O))O)))))))))C=O)O
Scaffold Graph/Node/Bond level: O=C(OC1CC=CCC1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)C1CCCCC1
Functional groups: CO; CC(C(=O)O)=CC; cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
3-o-galloylshikimic acid
External chemical identifiers:
CID:CID_460897; ChEMBL:CHEMBL289369; ZINC:ZINC000006524391; FDASRS:9XEH2JM56J; MolPort-005-945-490
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-Galloylshikimic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.26
Log P RDKit -0.53
Topological polar surface area (Å2) RDKit 164.75
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
5-Galloylshikimic 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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.315976
5-Galloylshikimic 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 -8.69
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 No