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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
Data?1588100009
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
Disposition

Biological location

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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.57231661259
DarkChem[M-H]-173.57631661259
DeepCCS[M+H]+166.17930932474
DeepCCS[M-H]-163.82130932474
DeepCCS[M-2H]-197.75530932474
DeepCCS[M+Na]+172.91830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SinapineCOC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O3883.7Standard polar33892256
SinapineCOC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O2277.2Standard non polar33892256
SinapineCOC1=CC(\C=C\C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O2431.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sinapine,1TMS,isomer #1COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O[Si](C)(C)C2461.0Semi standard non polar33892256
Sinapine,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)OCC[N+](C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2710.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sinapine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9340000000-63c6b1f491d1742f581e2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapine GC-MS (1 TMS) - 70eV, Positivesplash10-07r9-9083000000-01fd82cd03199a2410f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0ik9-0069000000-dae71e5c3cb5e8c98d012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-689b623cad4015ad43052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0kdi-0980000000-e85059fdfaf38b65fbf32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0092000000-57b6d7af206f0f8438e32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-c865ce6a2d45509c56362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0090000000-c860008ae94305bdbb562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0udi-0390000000-fe4aa2449788245232592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-QTOF , positive-QTOFsplash10-0kdj-0950000000-61508103ba9b618dbf8f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-bf3c90800cc09e89c5132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-e6a2d2e0e7afaaa895942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-c17f367eb5b6d7c376922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapine LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-4b0ecc4ed11995be10062017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
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.. .