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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-22 16:34:52 UTC
Update Date2021-09-22 16:34:52 UTC
HMDB IDHMDB0301714
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Sinapoylquinic acid
Description5-sinapoylquinic acid belongs to quinic acids and derivatives class of compounds. Those are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 5-sinapoylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 5-sinapoylquinic acid can be found in a number of food items such as apple, european plum, sour cherry, and pear, which makes 5-sinapoylquinic acid a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
5-O-SinapoylquinateGenerator
5-SinapoylquinateGenerator
Chemical FormulaC18H22O10
Average Molecular Weight398.3613
Monoisotopic Molecular Weight398.121296924
IUPAC Name(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
Traditional Name(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)O[C@@H]2C[C@@](O)(C[C@@H](O)[C@H]2O)C(O)=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C18H22O10/c1-26-11-5-9(6-12(27-2)16(11)22)3-4-14(20)28-13-8-18(25,17(23)24)7-10(19)15(13)21/h3-6,10,13,15,19,21-22,25H,7-8H2,1-2H3,(H,23,24)/b4-3+/t10-,13-,15-,18+/m1/s1
InChI KeyDTJWTKVKHOJHJK-RVBNATNPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
Substituents
  • Quinic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Phenol
  • Alkyl aryl ether
  • Fatty acid ester
  • Cyclohexanol
  • Fatty acyl
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Alpha-hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Ether
  • Polyol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.29ALOGPS
logP-0.28ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area162.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.18 m³·mol⁻¹ChemAxon
Polarizability38.39 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+192.24632859911
AllCCS[M+H-H2O]+189.67132859911
AllCCS[M+Na]+195.29532859911
AllCCS[M+NH4]+194.61632859911
AllCCS[M-H]-189.00832859911
AllCCS[M+Na-2H]-189.44132859911
AllCCS[M+HCOO]-190.05732859911
DeepCCS[M+H]+190.76230932474
DeepCCS[M-H]-188.49630932474
DeepCCS[M-2H]-221.76430932474
DeepCCS[M+Na]+196.67430932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 10V, Positive-QTOFsplash10-0kc2-0539000000-37be5ca6f2451272f8e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 20V, Positive-QTOFsplash10-0a6r-0934000000-f24c14484ec201b47c892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 40V, Positive-QTOFsplash10-004i-0910000000-0ba64cc1be924decbebc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 10V, Negative-QTOFsplash10-0f6t-0229000000-6011dad615ca9e06db102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 20V, Negative-QTOFsplash10-0f72-1937000000-8e1f024ea9e853bdd4892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 40V, Negative-QTOFsplash10-0002-0920000000-91638b0e5d7bc86162172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 10V, Positive-QTOFsplash10-002b-0439000000-95cbf6d07fe2f4a2f3032021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 20V, Positive-QTOFsplash10-056r-0961000000-5dc7e2b6da6b5f5c65c42021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 40V, Positive-QTOFsplash10-004i-2951000000-d8c5336c7124f89f39432021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 10V, Negative-QTOFsplash10-0006-0902000000-bfa0b84bb0b947bd419d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 20V, Negative-QTOFsplash10-006y-2900000000-2ac6a1e41320848ddfe42021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Sinapoylquinic acid 40V, Negative-QTOFsplash10-0006-2911000000-3cb56fdbc1c293abde2a2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
FooDB IDFDB000250
KNApSAcK IDNot Available
Chemspider ID30785643
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound72193641
PDB IDNot Available
ChEBI ID75497
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available