Identification

PhytoHub ID
PHUB000639
Name
Sinapine
Systematic Name
Not Available
Synonyms
  • 4-Hydroxy-3,5-dimethoxycinnamate choline
  • Sinapic acid choline ester
CAS Number
Not Available
Average Mass
310.369
Monoisotopic Mass
310.164899297
Chemical Formula
C16H24NO5
IUPAC Name
(2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium
InChI Key
HUJXHFRXWWGYQH-UHFFFAOYSA-O
InChI Identifier
InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
SMILES
COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O
Structure

Calculated Properties

Solubility (ALOGPS)
1.41e-02 g/l
LogS (ALOGPS)
-4.39
LogP (ALOGPS)
-0.93
Hydrogen Acceptors
4
Hydrogen Donors
1
Rotatable Bond Count
8
Polar Surface Area
64.99000000000001
Refractivity
96.669
Polarizability
34.32545227228419
Formal Charge
1
Physiological Charge
1
pKa (strongest basic)
-4.602090062685847
pKa (strongest acidic)
9.288740484436033
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Hydroxycinnamic acids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Cinnamic acids and derivatives
Super-class
Phenylpropanoids and polyketides
Sub-class
Hydroxycinnamic acids and derivatives
Direct Parent Name
Coumaric acids and derivatives
Alternative Parent Names
["Acyl cholines", "Alkyl aryl ethers", "Amines", "Anisoles", "Carbonyl compounds", "Cinnamic acid esters", "Dimethoxybenzenes", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Methoxyphenols", "Monocarboxylic acids and derivatives", "Organic cations", "Organic oxides", "Organic salts", "Organopnictogen compounds", "Phenoxy compounds", "Styrenes", "Tetraalkylammonium salts"]
External Descriptor Annotations
["Sinapate derivatives", "a small molecule", "acylcholine"]
Substituent Names
["Acyl choline", "Alkyl aryl ether", "Alpha,beta-unsaturated carboxylic ester", "Amine", "Anisole", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid derivative", "Carboxylic acid ester", "Cinnamic acid ester", "Coumaric acid or derivatives", "Dimethoxybenzene", "Enoate ester", "Ether", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "M-dimethoxybenzene", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic cation", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organic salt", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Phenol", "Phenol ether", "Phenoxy compound", "Quaternary ammonium salt", "Styrene", "Tetraalkylammonium salt"]

Spectra from Online Resources

Record IDSourceDescriptionView
CE000051MassBankLC-ESI-ITFT Spectrum - 35eV, unspecifiedView Spectra
CE000052MassBankLC-ESI-ITFT Spectrum - 45eV, unspecifiedView Spectra
CE000053MassBankLC-ESI-ITFT Spectrum - 55eV, unspecifiedView Spectra
CE000054MassBankLC-ESI-ITFT Spectrum - 70eV, unspecifiedView Spectra
CE000055MassBankLC-ESI-ITFT Spectrum - -, unspecifiedView Spectra
PS118201ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS118202ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS118203ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS118204ReSpectN/A Spectrum - 40, [M+H]+View Spectra

Food Sources

NameGroup
RapeseedOilseed cropsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

No metabolism information available

Inter-Individual Variations in Metabolism

No data on inter-individual variations available

Back