IMPPAT Phytochemical information: 
1-O-beta-D-Glucopyranosyl anthranilate

1-O-beta-D-Glucopyranosyl anthranilate
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)c2ccccc2N)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C13H17NO7/c14-7-4-2-1-3-6(7)12(19)21-13-11(18)10(17)9(16)8(5-15)20-13/h1-4,8-11,13,15-18H,5,14H2/t8-,9-,10+,11-,13+/m1/s1
InChIKey: GTQKOJVFDJDUGN-HMUNZLOLSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)cccccc6N)))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CCCCO1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CCCCO1)C1CCCCC1
Scaffold Graph level: CC(CC1CCCCC1)C1CCCCC1
Functional groups: CO; cC(=O)O[C@@H](C)OC; cN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
anthranilic-acid-glucoside, anthraniloyl-o-glucose
External chemical identifiers:
CID:CID_70684367; ChEMBL:CHEMBL2063298; ChEBI:CHEBI:176467; ZINC:ZINC000084713199
Chemical structure download


1-O-beta-D-Glucopyranosyl anthranilate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 299.28
Log P RDKit -1.77
Topological polar surface area (Å2) RDKit 142.47
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


1-O-beta-D-Glucopyranosyl anthranilate
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 Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.325702


1-O-beta-D-Glucopyranosyl anthranilate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 0
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