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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:51:13 UTC
Update Date2022-03-07 02:53:58 UTC
HMDB IDHMDB0034069
Secondary Accession Numbers
  • HMDB34069
Metabolite Identification
Common Namecis-Sinapic acid
Descriptioncis-Sinapic acid, also known as cis-sinapate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. cis-Sinapic acid has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make cis-sinapic acid a potential biomarker for the consumption of these foods. cis-Sinapic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on cis-Sinapic acid.
Structure
Data?1563862504
Synonyms
ValueSource
(Z)-4-Hydroxy-3,5-dimethoxycinnamic acidChEBI
cis-4-Hydroxy-3,5-dimethoxycinnamic acidChEBI
(Z)-4-Hydroxy-3,5-dimethoxycinnamateGenerator
cis-4-Hydroxy-3,5-dimethoxycinnamateGenerator
cis-SinapateGenerator
trans-Sinapinic acidMeSH, HMDB
3,5-Dimethoxy-4-hydroxycinnamic acidMeSH, HMDB
(e)-Sinapic acidMeSH, HMDB
Sinapic acidMeSH, HMDB
Sinapinic acidMeSH, HMDB
Synapitic acidMeSH, HMDB
4-Hydroxy-3,5-dimethoxycinnamic acidMeSH, HMDB
trans-Sinapic acidMeSH, HMDB
(2Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
(Z)-3,5-Dimethoxy-4-hydroxycinnamic acidHMDB
(Z)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylic acidHMDB
(Z)-Sinapic acidHMDB
3,5-Dimethoxy-4-hydroxy-cis-cinnamic acidHMDB
3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenoic acidHMDB
Z-Sinapinic acidHMDB
cis-Sinapic acidHMDB
cis-Sinapinic acidHMDB
Chemical FormulaC11H12O5
Average Molecular Weight224.21
Monoisotopic Molecular Weight224.068473494
IUPAC Name(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Traditional Name(2Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
CAS Registry Number7361-90-2
SMILES
COC1=CC(\C=C/C(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3-
InChI KeyPCMORTLOPMLEFB-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
  • 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid (CHEBI:76350 )
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7082 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP1.63ALOGPS
logP1.52ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability21.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+151.20330932474
DeepCCS[M-H]-148.84630932474
DeepCCS[M-2H]-182.33330932474
DeepCCS[M+Na]+157.33230932474
AllCCS[M+H]+149.532859911
AllCCS[M+H-H2O]+145.532859911
AllCCS[M+NH4]+153.232859911
AllCCS[M+Na]+154.232859911
AllCCS[M-H]-148.232859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-149.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-Sinapic acidCOC1=CC(\C=C/C(O)=O)=CC(OC)=C1O3815.2Standard polar33892256
cis-Sinapic acidCOC1=CC(\C=C/C(O)=O)=CC(OC)=C1O2004.3Standard non polar33892256
cis-Sinapic acidCOC1=CC(\C=C/C(O)=O)=CC(OC)=C1O2149.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-Sinapic acid,1TMS,isomer #1COC1=CC(/C=C\C(=O)O[Si](C)(C)C)=CC(OC)=C1O2214.3Semi standard non polar33892256
cis-Sinapic acid,1TMS,isomer #2COC1=CC(/C=C\C(=O)O)=CC(OC)=C1O[Si](C)(C)C2169.8Semi standard non polar33892256
cis-Sinapic acid,2TMS,isomer #1COC1=CC(/C=C\C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C2201.5Semi standard non polar33892256
cis-Sinapic acid,1TBDMS,isomer #1COC1=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O2477.7Semi standard non polar33892256
cis-Sinapic acid,1TBDMS,isomer #2COC1=CC(/C=C\C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2451.1Semi standard non polar33892256
cis-Sinapic acid,2TBDMS,isomer #1COC1=CC(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2735.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-Sinapic acid GC-MS (2 TMS)splash10-00kr-3659000000-141953a5d5d848f1aa512014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Sinapic acid GC-MS (Non-derivatized)splash10-00kr-3659000000-141953a5d5d848f1aa512017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-Sinapic acid GC-EI-TOF (Non-derivatized)splash10-000i-2958000000-16d208a44d4442af41c52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Sinapic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-1960000000-e20c10aa0bcc765f8c282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Sinapic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0umi-8196000000-afceb35e7a5f28ec225c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-Sinapic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 10V, Positive-QTOFsplash10-056r-0190000000-6e81a94093485194a43f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 20V, Positive-QTOFsplash10-004i-1960000000-18717b9e874f0901ea682016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 40V, Positive-QTOFsplash10-06vj-2900000000-254ee08e710708eb65452016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 10V, Negative-QTOFsplash10-00di-0190000000-89ae701e731ef1f24fd72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 20V, Negative-QTOFsplash10-00di-0890000000-74c0bdbe7769b328017a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 40V, Negative-QTOFsplash10-0a4i-1910000000-69bbc48ce24397a342a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 10V, Positive-QTOFsplash10-0a6r-0290000000-9de305bfb1242c5c3e102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 20V, Positive-QTOFsplash10-056r-0980000000-368fb5936979c9a6e99d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 40V, Positive-QTOFsplash10-0aor-3900000000-395e080ff0323f7c60bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 10V, Negative-QTOFsplash10-00di-0090000000-cfca81bd3cf2894d0d6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 20V, Negative-QTOFsplash10-03di-0900000000-e363c6280db16d0c6ea72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Sinapic acid 40V, Negative-QTOFsplash10-00dl-8930000000-4fe3d11040b797e9d2112021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012318
KNApSAcK IDNot Available
Chemspider ID1266059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549091
PDB IDNot Available
ChEBI ID76350
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1840221
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.. .