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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:04 UTC
Update Date2019-07-23 06:03:57 UTC
HMDB IDHMDB0029379
Secondary Accession Numbers
  • HMDB29379
Metabolite Identification
Common NameSinapine
DescriptionNapin is found in brassicas. Storage protein isolated from the seeds of Brassica napus (rape).
Structure
Data?1563861837
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
Chemical FormulaC16H24NO5
Average Molecular Weight310.3655
Monoisotopic Molecular Weight310.165447883
IUPAC Name(2-{[(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium
CAS Registry Number18696-26-9
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP-0.93ALOGPS
logP-2.2ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.67 m³·mol⁻¹ChemAxon
Polarizability32.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9340000000-63c6b1f491d1742f581eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-07r9-9083000000-01fd82cd03199a2410f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-0069000000-dae71e5c3cb5e8c98d01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-689b623cad4015ad4305JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kdi-0980000000-e85059fdfaf38b65fbf3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0092000000-57b6d7af206f0f8438e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-c865ce6a2d45509c5636JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-c860008ae94305bdbb56JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-fe4aa244978824523259JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kdj-0950000000-61508103ba9b618dbf8fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-bf3c90800cc09e89c513JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-e6a2d2e0e7afaaa89594JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-c17f367eb5b6d7c37692JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-4b0ecc4ed11995be1006JSpectraViewer | MoNA
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
FoodDB IDFDB000456
KNApSAcK IDC00002777
Chemspider ID80576
KEGG Compound IDC00933
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSinapine
METLIN IDNot Available
PubChem Compound89287
PDB IDNot Available
ChEBI ID16353
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.. .