IMPPAT Phytochemical information: 
((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate
((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate
Summary

SMILES: O=C(c1ccccc1)OC[C@@]1(O)[C@@H](O)C=C[C@H]([C@@H]1O)OC(=O)c1ccccc1
InChI: InChI=1S/C21H20O7/c22-17-12-11-16(28-20(25)15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16-18,22-23,26H,13H2/t16-,17+,18+,21-/m1/s1
InChIKey: AWCUZBLYCWUTRL-OEMYIYORSA-N
DeepSMILES: O=Ccccccc6))))))OC[C@@]O)[C@@H]O)C=C[C@H][C@@H]6O))OC=O)cccccc6
Scaffold Graph/Node/Bond level: O=C(OCC1CC=CC(OC(=O)c2ccccc2)C1)c1ccccc1
Scaffold Graph/Node level: OC(OCC1CCCC(OC(O)C2CCCCC2)C1)C1CCCCC1
Scaffold Graph level: CC(CCC1CCCC(CC(C)C2CCCCC2)C1)C1CCCCC1
Functional groups: cC(=O)OC; CO; CC=CC
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:
zeylenol
External chemical identifiers:
CID:CID_10992619; ChEMBL:CHEMBL4469789; ZINC:ZINC000091297329
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.38
Log P RDKit 1.09
Topological polar surface area (Å2) RDKit 113.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.522376
((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate
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 High
Log Kp (Skin permeation, cm/s) SwissADME -7.57
Number of PAINS structural alerts SwissADME 0
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 Yes