IMPPAT Phytochemical information: 
1-O-Sinapoyl-beta-D-glucose
1-O-Sinapoyl-beta-D-glucose
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)/C=C/c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
InChIKey: XRKBRPFTFKKHEF-DGDBGZAXSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)/C=C/cccOC))ccc6)OC)))O)))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCCCO1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCCCO1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCCCC1
Functional groups: CO; c/C=C/C(=O)O[C@@H](C)OC; cOC; 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
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
beta-d-glucopyranosyl ester-(e)-sinapic acid, 1-o-sinapoyl-beta-d-glucose, trans-sinapic acid glucoside
External chemical identifiers:
CID:CID_5280406; ChEBI:CHEBI:16546; ZINC:ZINC000004095571; SureChEMBL:SCHEMBL546910
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-O-Sinapoyl-beta-D-glucose
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.35
Log P RDKit -1.23
Topological polar surface area (Å2) RDKit 155.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
1-O-Sinapoyl-beta-D-glucose
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.296215
1-O-Sinapoyl-beta-D-glucose
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.90
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 No