Record Information
Version1.0
Creation date2010-04-08 22:06:06 UTC
Update date2019-11-26 02:59:51 UTC
Primary IDFDB004152
Secondary Accession Numbers
  • FDB013889
  • FDB000456
Chemical Information
FooDB NameSinapin
DescriptionSugar phosphate, also known as sinapoylcholine or sinapine, belongs to coumaric acids and derivatives class of compounds. Those 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. Sugar phosphate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Sugar phosphate can be found in a number of food items such as common sage, tea leaf willow, broccoli, and sweet bay, which makes sugar phosphate a potential biomarker for the consumption of these food products. Sugar phosphate exists in all living organisms, ranging from bacteria to humans.
CAS Number18696-26-9
Structure
Thumb
Synonyms
SynonymSource
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
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
Polarizability34.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H24NO5
IUPAC name(2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC(\C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O
Average Molecular Weight310.3655
Monoisotopic Molecular Weight310.165447883
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSinapine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9340000000-63c6b1f491d1742f581eSpectrum
Predicted GC-MSSinapine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-07r9-9083000000-01fd82cd03199a2410f7Spectrum
Predicted GC-MSSinapine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-0069000000-dae71e5c3cb5e8c98d01Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-689b623cad4015ad4305Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kdi-0980000000-e85059fdfaf38b65fbf3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0092000000-57b6d7af206f0f8438e3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-c865ce6a2d45509c5636Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0090000000-c860008ae94305bdbb56Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-fe4aa244978824523259Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kdj-0950000000-61508103ba9b618dbf8fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-bf3c90800cc09e89c513Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-e6a2d2e0e7afaaa89594Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-c17f367eb5b6d7c37692Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-4b0ecc4ed11995be1006Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSINAPIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).