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Record Information
Version1.0
Created at2022-09-05 23:36:35 UTC
Updated at2022-09-05 23:36:35 UTC
NP-MRD IDNP0221913
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r,4s,5s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Description(2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. (2s,3r,4s,5s)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is found in Triticum aestivum. Based on a literature review very few articles have been published on (2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(2S,3R,4S,5S)-2-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC37H38O18
Average Mass770.6930 Da
Monoisotopic Mass770.20581 Da
IUPAC Name(2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Traditional Name(2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-6-yl]-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2C2=C(O)C([C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C=C2)=CC(OC)=C1O
InChI Identifier
InChI=1S/C37H38O18/c1-50-20-9-14(10-21(51-2)28(20)44)3-8-23(42)55-37-27(43)18(41)13-52-36(37)25-30(46)24-17(40)11-19(15-4-6-16(39)7-5-15)53-34(24)26(31(25)47)35-33(49)32(48)29(45)22(12-38)54-35/h3-11,18,22,27,29,32-33,35-39,41,43-49H,12-13H2,1-2H3/b8-3+/t18-,22+,27-,29-,32-,33+,35-,36-,37+/m0/s1
InChI KeyLZPTZBKFVPQQHO-HWQXPBHNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Triticum aestivumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • M-dimethoxybenzene
  • 1-benzopyran
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.24ChemAxon
pKa (Strongest Acidic)5.74ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area291.82 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity187.66 m³·mol⁻¹ChemAxon
Polarizability74.76 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163185587
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]