IMPPAT Phytochemical information: 
Cinnzeylanin
Cinnzeylanin
Summary

SMILES: CC(=O)O[C@@H]1[C@@H](C)CC[C@]2([C@@]31O[C@@]1([C@@]4([C@@]3(O)[C@@]([C@]2(C1)C)(O)C[C@]4(O)C(C)C)C)O)O
InChI: InChI=1S/C22H34O8/c1-11(2)17(24)10-19(26)15(5)9-20(27)16(17,6)22(19,28)21(30-20)14(29-13(4)23)12(3)7-8-18(15,21)25/h11-12,14,24-28H,7-10H2,1-6H3/t12-,14+,15-,16+,17-,18-,19+,20-,21+,22+/m0/s1
InChIKey: DFYFOAFKHRTQLA-PIKMFBPASA-N
DeepSMILES: CC=O)O[C@@H][C@@H]C)CC[C@][C@]6O[C@@][C@@][C@@]5O)[C@@][C@]8C6)C))O)C[C@]5O)CC)C))))))C))O))))O
Scaffold Graph/Node/Bond level: C1CCC23OC4CC(C5CCC4C52)C3C1
Scaffold Graph/Node level: C1CCC23OC4CC(C5CCC4C52)C3C1
Scaffold Graph level: C1CCC23CC4CC(C5CCC4C52)C3C1
Functional groups: CC(=O)OC; C[C@@](O)(C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
Synonymous chemical names:
cinnzeylanin, cinnazeylanin, cinnazeylani, cinnzeylanine
External chemical identifiers:
CID:CID_101306938; ZINC:ZINC000238774943
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cinnzeylanin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 426.51
Log P RDKit 0.22
Topological polar surface area (Å2) RDKit 136.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 21
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Cinnzeylanin
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.395687
Cinnzeylanin
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 -9.09
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 Yes