IMPPAT Phytochemical information: 
Shikimic acid

Shikimic acid
Summary

SMILES: O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O
InChI: InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
InChIKey: JXOHGGNKMLTUBP-HSUXUTPPSA-N
DeepSMILES: O[C@@H]CC=C[C@H][C@H]6O))O)))C=O)O
Scaffold Graph/Node/Bond level: C1=CCCCC1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CO; CC(C(=O)O)=CC
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: Phenolic acids (C6-C1)
NP Classifier Class: Shikimic acids and derivatives
Synonymous chemical names:
Shikimic acid, shikimic acid,(-)-, (-)-shikimic acid, shikimic acid, shikimic-acid, shikimic
External chemical identifiers:
CID:CID_8742; ChEMBL:CHEMBL290345; ChEBI:CHEBI:16119; ZINC:ZINC000003860720; FDASRS:29MS2WI2NU; SureChEMBL:SCHEMBL43377; MolPort-002-507-279
Chemical structure download


Shikimic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 174.15
Log P RDKit -1.52
Topological polar surface area (Å2) RDKit 97.99
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 7
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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


Shikimic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.39


Shikimic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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


Shikimic acid
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000365534THNSL1750
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.