IMPPAT Phytochemical information: 
Sinapine (thiocyanate)

Sinapine (thiocyanate)
Summary

SMILES: COc1cc(C=CC(=O)OCC[N+](C)(C)C)cc(c1O)OC.[S-]C#N
InChI: InChI=1S/C16H23NO5.CHNS/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5;2-1-3/h6-7,10-11H,8-9H2,1-5H3;3H
InChIKey: YLELSNOPYHTYTB-UHFFFAOYSA-N
DeepSMILES: COcccC=CC=O)OCC[N+]C)C)C))))))))ccc6O))OC.[S-]C#N
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cOC; cC=CC(=O)OC; C[N+](C)(C)C; cO; N#C[S-]
Chemical classification

Synonymous chemical names:
Sinapine thiocyanate
External chemical identifiers:
CID:CID_73867336; FDASRS:A9SJB3RPE2; SureChEMBL:SCHEMBL9334027; MolPort-046-418-652
Chemical structure download


Sinapine (thiocyanate)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.46
Log P RDKit 1.69
Topological polar surface area (Å2) RDKit 88.78
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
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 1


Sinapine (thiocyanate)
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 0.257489


Sinapine (thiocyanate)
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 -6.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
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