Showing Compound Card for Sinapyl alcohol (CDB005039)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 19:03:09 UTC
Updated at2020-11-18 16:39:14 UTC
CannabisDB IDCDB005039
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSinapyl alcohol
DescriptionSinapyl alcohol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Sinapyl alcohol is a precursor to lignin or lignans. Sinapyl alcohol is an organic compound derived from cinnamic acid. This phytochemical is one of the monolignols. Sinapyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sinapyl alcohol has been detected, but not quantified in, several different foods, such as corn salad, dates, rapinis, oats, and black cabbages. This could make sinapyl alcohol a potential biomarker for the consumption of these foods. It is also a biosynthetic precursor to various stilbenes and coumarins. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. Sinapyl alcohol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-Sinapoyl alcoholChEBI
Sinapoyl alcoholChEBI
(e)-Sinapyl alcoholChEBI, HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propen-1-olHMDB
4-(3-Hydroxy-1-propenyl)-2,6-dimethoxy-phenolHMDB
4-(3-Hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenolHMDB
4-Hydroxy-3,5-dimethoxycinnamyl alcoholHMDB
Sinapic alcoholHMDB
Sinapyl alcohol(e)HMDB
Sinapyl-alcoholHMDB
Sinapyl alcoholMeSH
trans-Sinapoyl alcoholChEBI
Chemical FormulaC11H14O4
Average Molecular Weight210.23
Monoisotopic Molecular Weight210.0892
IUPAC Name4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol
Traditional Namesinapyl alcohol
CAS Registry Number537-33-7
SMILES
COC1=CC(\C=C\CO)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3+
InChI KeyLZFOPEXOUVTGJS-ONEGZZNKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Cinnamyl alcohol
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.36ALOGPS
logP1.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.1 m³·mol⁻¹ChemAxon
Polarizability22.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSinapyl alcohol, 2 TMS, GC-MS Spectrumsplash10-0ul0-1498000000-f1ff8135d3d6a46d0d5fSpectrum
GC-MSSinapyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0ul0-1498000000-f1ff8135d3d6a46d0d5fSpectrum
GC-MSSinapyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0ff0-1963000000-a61969c3a51056cf2757Spectrum
GC-MSSinapyl alcohol, non-derivatized, GC-MS Spectrumsplash10-06rl-1591000000-cc313a08a2a4a462462cSpectrum
Predicted GC-MSSinapyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02c6-1910000000-483f5859b80c81006212Spectrum
Predicted GC-MSSinapyl alcohol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9176000000-a74c5b86187073be58d2Spectrum
Predicted GC-MSSinapyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4i-0090000000-602a2e14b33c30c3e91a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-00di-0009100000-36f51ff1821919e02dca2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-0006-0900000000-3a73e5daddcd05b7914d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-03di-0900000000-be9c70dc000fe516c98e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-002b-0900000000-dd341f985c8717688c862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0a4i-0390000000-23fd3e2b83322f5cbdf72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-03dl-0900000000-7590f4f1f32763b2765b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-03dl-0900000000-20d8d646de0bb37740902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-03di-0900000000-caf158fef19ad3b6bb652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-03di-0900000000-fb34fca92160edf417372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-03e9-0900000000-1ab7dc6b13aeb403011b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0bu0-0900000000-e5d28e66343eef2876db2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0api-1900000000-a5be2f9ca060395b24fa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0api-1900000000-12d11ae51510e9082ac12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-069r-3900000000-b6fa51093a215d65de962020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0690-3900000000-146837c3a0ceff99347f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0lfu-6900000000-d563c428d1b44f2113772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-00ou-9800000000-79fe37355291b2e02ae22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0fvl-9700000000-e9c1d0f950c1d92969342020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0960000000-05c3f14530ede23c5f4c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1910000000-e9785ad5d3c4cf38a2952017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-6900000000-6d2245e76d3fd5d9892a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-5e2811f643e53b1ae5ba2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0930000000-04bca1d7fd2e630f64762017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-3900000000-fe0913e64f24e42bd7732017-09-01View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Peroxiredoxin-6PRDX61q25.1P30041 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0013070
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029281
KNApSAcK IDC00002778
Chemspider ID4444145
KEGG Compound IDC02325
BioCyc IDSINAPYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkSinapyl alcohol
METLIN IDNot Available
PubChem Compound5280507
PDB ID55B
ChEBI ID64557
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Peroxiredoxin-6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715