IMPPAT Phytochemical information: 
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Summary

SMILES: OC(=O)C1=CC(=O)C2(C(C1c1c(cc(c(c1O2)O)O)C(=O)O)(O)O)O
InChI: InChI=1S/C14H10O11/c15-5-1-3(11(18)19)7-8-4(12(20)21)2-6(16)14(24,13(8,22)23)25-10(7)9(5)17/h1-2,8,15,17,22-24H,(H,18,19)(H,20,21)
InChIKey: ZMIDWLVYIBGXNC-UHFFFAOYSA-N
DeepSMILES: OC=O)C=CC=O)CCC6cccccc6O%10))O))O)))C=O)O)))))O)O))O
Scaffold Graph/Node/Bond level: O=C1C=CC2CC1Oc1ccccc12
Scaffold Graph/Node level: OC1CCC2CC1OC1CCCCC21
Scaffold Graph level: CC1CCC2CC1CC1CCCCC12
Functional groups: cOC1(O)C(=O)C=C(C(=O)O)CC1(O)O; cO; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Simple phenolic acids
Synonymous chemical names:
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Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
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Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.22
Log P RDKit -1.76
Topological polar surface area (Å2) RDKit 202.05
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
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Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
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 0.23
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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 -10.04
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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