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Record Information
Version2.0
Created at2022-09-12 01:01:21 UTC
Updated at2022-09-12 01:01:22 UTC
NP-MRD IDNP0322317
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5-{[2-(4-acetylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxy-3,5-dimethoxybenzoate
Description4'-Hydroxyacetophenone 4'-[4-hydroxy-3,5-dimethoxybenzoyl-(->5)-apiosyl-(1->2)-glucoside] belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 4'-Hydroxyacetophenone 4'-[4-hydroxy-3,5-dimethoxybenzoyl-(->5)-apiosyl-(1->2)-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4'-Hydroxyacetophenone 4'-[4-hydroxy-3,5-dimethoxybenzoyl-(->5)-apiosyl-(1->2)-glucoside] has been detected, but not quantified in, herbs and spices and tea. (5-{[2-(4-acetylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxy-3,5-dimethoxybenzoate is found in Salvia officinalis and Thymus vulgaris. This could make 4'-hydroxyacetophenone 4'-[4-hydroxy-3,5-dimethoxybenzoyl-(->5)-apiosyl-(1->2)-glucoside] a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
(5-{[2-(4-acetylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxy-3,5-dimethoxybenzoic acidGenerator
Chemical FormulaC28H34O15
Average Mass610.5606 Da
Monoisotopic Mass610.18977 Da
IUPAC Name(5-{[2-(4-acetylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxy-3,5-dimethoxybenzoate
Traditional Name(5-{[2-(4-acetylphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxy-3,5-dimethoxybenzoate
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1O)C(=O)OCC1(O)COC(OC2C(O)C(O)C(CO)OC2OC2=CC=C(C=C2)C(C)=O)C1O
InChI Identifier
InChI=1S/C28H34O15/c1-13(30)14-4-6-16(7-5-14)41-26-23(22(33)21(32)19(10-29)42-26)43-27-24(34)28(36,12-40-27)11-39-25(35)15-8-17(37-2)20(31)18(9-15)38-3/h4-9,19,21-24,26-27,29,31-34,36H,10-12H2,1-3H3
InChI KeyDPDBFIMFRJQAKL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Salvia officinalisLOTUS Database
Thymus vulgarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Phenolic glycoside
  • Alkyl-phenylketone
  • Gallic acid or derivatives
  • O-glycosyl compound
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • M-methoxybenzoic acid or derivatives
  • Glycosyl compound
  • Disaccharide
  • Methoxyphenol
  • Benzoate ester
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Benzoic acid or derivatives
  • Phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Tertiary alcohol
  • Tetrahydrofuran
  • Ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.26ALOGPS
logP-0.44ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area220.13 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity141.99 m³·mol⁻¹ChemAxon
Polarizability60.74 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0036333
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015204
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85245577
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]