IMPPAT Phytochemical information: 
Grandidentatin
Grandidentatin
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2CCCC[C@@H]2O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C21H28O9/c22-11-16-18(26)19(27)20(21(29-16)28-15-4-2-1-3-14(15)24)30-17(25)10-7-12-5-8-13(23)9-6-12/h5-10,14-16,18-24,26-27H,1-4,11H2/b10-7+/t14-,15+,16+,18+,19-,20+,21+/m0/s1
InChIKey: ZTMPDTJBTNGZJH-QMZLQNRASA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]CCCC[C@@H]6O))))))))[C@@H][C@H][C@@H]6O))O))OC=O)/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCOC1OC1CCCCC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCOC1OC1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1CC1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; c/C=C/C(=O)OC; 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:
grandidentatin
External chemical identifiers:
CID:CID_5281776; ChEMBL:CHEMBL3327187; ChEBI:CHEBI:5534; ZINC:ZINC000004098733
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Grandidentatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.45
Log P RDKit 0.08
Topological polar surface area (Å2) RDKit 145.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 7
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Grandidentatin
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 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.32
Grandidentatin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.25
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 Yes