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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:37:39 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030564
Secondary Accession Numbers
  • HMDB30564
Metabolite Identification
Common Nametrans-Piceid
Descriptiontrans-Piceid, also known as polydatin or piceid, belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Thus, trans-piceid is considered to be an aromatic polyketide. trans-Piceid is found, on average, in the highest concentration within a few different foods, such as grape wine, white wine, and berry wine and in a lower concentration in peanuts (Arachis hypogaea), chocolate, and common grapes (Vitis vinifera). trans-Piceid has also been detected, but not quantified in, several different foods, such as lingonberries (Vaccinium vitis-idaea), garden tomatoes (Solanum lycopersicum), alcoholic beverages, red grape juice, and strawberries (Fragaria X ananassa). This could make trans-piceid a potential biomarker for the consumption of these foods. trans-Piceid 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 a significant number of articles have been published on trans-Piceid.
Structure
Thumb
Synonyms
Chemical FormulaC20H22O8
Average Molecular Weight390.388
Monoisotopic Molecular Weight390.131467668
IUPAC Name(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Namepiceid
CAS Registry Number27208-80-6
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=CC(\C=C\C3=CC=C(O)C=C3)=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
InChI KeyHSTZMXCBWJGKHG-CUYWLFDKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassStilbene glycosides
Direct ParentStilbene glycosides
Alternative Parents
Substituents
  • Stilbene glycoside
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 140 °CNot Available
Boiling Point707.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1616 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.412 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDDB11263
Phenol Explorer Compound ID593
FooDB IDFDB002449
KNApSAcK IDC00002896
Chemspider ID4445034
KEGG Compound IDC10275
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281718
PDB IDNot Available
ChEBI ID8198
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1589071
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.. .