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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:04 UTC
Update Date2022-03-07 02:52:08 UTC
HMDB IDHMDB0029379
Secondary Accession Numbers
  • HMDB29379
Metabolite Identification
Common NameSinapine
DescriptionSinapine (CAS: 18696-26-9), also known as sinapoylcholine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Sinapine is an extremely weak basic (essentially neutral) compound (based on its pKa). Sinapine has been detected, but not quantified, in garden cress and horseradish. Sinapine is found in brassicas. It is a storage protein isolated from the seeds of Brassica napus (rape). This could make sinapine a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
2-(4-Hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminiumChEBI
O-SinapoylcholineChEBI
SinapoylcholineChEBI
2-[[3-(4-Hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl]oxy]-N,N,N- trimethylethanaminium, 9ciHMDB
4-Hydroxy-3,5-dimethoxycinnamate cholineHMDB
Choline 4-hydroxy-3,5-dimethoxycinnamate, 8ciHMDB
Sinapine bisulfateHMDB
Sinapine bisulphateHMDB
Sugar phosphoric acidHMDB
trans-SinapineHMDB
trans-SinapoylcholineHMDB
Chemical FormulaC16H24NO5
Average Molecular Weight310.3655
Monoisotopic Molecular Weight310.165447883
IUPAC Name(2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium
Traditional Namesinapine
CAS Registry Number84123-22-8
SMILES
COC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O
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
InChI KeyHUJXHFRXWWGYQH-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Acyl choline
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Phenoxy compound
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Enoate ester
  • Quaternary ammonium salt
  • Alpha,beta-unsaturated carboxylic ester
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxide
  • Organic salt
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6398 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-3.370 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID557
FooDB IDFDB004152
KNApSAcK IDC00002777
Chemspider ID80576
KEGG Compound IDC00933
BioCyc IDO-SINAPOYLCHOLINE
BiGG IDNot Available
Wikipedia LinkSinapine
METLIN IDNot Available
PubChem Compound89287
PDB IDNot Available
ChEBI ID16353
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1063401
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .