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Record Information
Version2.0
Created at2022-03-17 21:02:38 UTC
Updated at2022-03-17 21:02:39 UTC
NP-MRD IDNP0048817
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrilobatin
DescriptionTrilobatin, also known as p-phloridzin, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, trilobatin is considered to be a flavonoid lipid molecule. Trilobatin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Trilobatin has been detected, but not quantified in, pomes. Trilobatin is found in Balanophora harlandii, Balanophora tobiracola, Lithocarpus liseifolius, Lithocarpus litseifolius, Lithocarpus pachyphyllus, Lithocarpus polystachya, Lithocarpus polystachyus, Malus trilobata, Symplocos microcalyx, Vitis piasezkii, Vitis saccharifera and Vitis vinifera. This could make trilobatin a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
p-PhloridzinHMDB
p-PhlorizinHMDB
Phloretin-4'-O-glucosideMeSH
Chemical FormulaC21H24O10
Average Mass436.4093 Da
Monoisotopic Mass436.13695 Da
IUPAC Name1-(2,6-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
Traditional Nametrilobatin
CAS Registry Number4192-90-9
SMILES
OCC1OC(OC2=CC(O)=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2
InChI KeyGSTCPEBQYSOEHV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Balanophora harlandiiLOTUS Database
Balanophora tobiracolaLOTUS Database
Fragaria x ananassaFooDB
Lithocarpus liseifoliusPlant
Lithocarpus litseifoliusPlant
Lithocarpus pachyphyllusLOTUS Database
Lithocarpus polystachyaPlant
Lithocarpus polystachyusPlant
Malus trilobataPlant
Symplocos microcalyxPlant
Vitis piasezkiiPlant
Vitis sacchariferaPlant
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • 2'-hydroxy-dihydrochalcone
  • Linear 1,3-diarylpropanoid
  • Cinnamylphenol
  • Phenolic glycoside
  • Alkyl-phenylketone
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Butyrophenone
  • Phenylketone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Resorcinol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.45ALOGPS
logP1.63ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.85 m³·mol⁻¹ChemAxon
Polarizability43.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0037505
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016580
KNApSAcK IDC00007991
Chemspider ID24846091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13188898
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available