ChemFOnt: Showing chemical card for (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside] (CFc000335783)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:32 UTC

Chemfont ID

CFc000335783

Molecule Identification

Common Name

(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside]

Definition

Constituent of rice bran. (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside] is found in cereals and cereal products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetate 5-[glucosyl-(1->4)-b-D-glucoside]	Generator
2-(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2,3-dihydroxy-3H-indol-3-yl)acetate	Generator
(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetate 5-[glucosyl-(1->4)-glucoside]	Generator

Chemical Formula

C₂₂H₂₉NO₁₅

Average Molecular Weight

547.4634

Monoisotopic Molecular Weight

547.153719263

IUPAC Name

2-(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid

Traditional Name

(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-2-oxo-1H-indol-3-yl)acetic acid

CAS Registry Number

218604-48-9

SMILES

OCC1OC(OC2C(O)C(O)C(OC3=CC4=C(NC(=O)C4(O)CC(O)=O)C=C3)OC2CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H29NO15/c24-5-10-13(28)14(29)16(31)20(36-10)38-18-11(6-25)37-19(17(32)15(18)30)35-7-1-2-9-8(3-7)22(34,4-12(26)27)21(33)23-9/h1-3,10-11,13-20,24-25,28-32,34H,4-6H2,(H,23,33)(H,26,27)

InChI Key

ADONHDUDLSXBIZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Indolyl carboxylic acid derivative
Disaccharide
O-glycosyl compound
Indole
Indole or derivatives
Dihydroindole
Oxane
Benzenoid
Tertiary alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Azacycle
Acetal
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0034675)
Extracellular (HMDB: HMDB0034675)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034675)

Source

Exogenous

Exogenous (HMDB: HMDB0034675)

Food

Food (HMDB: HMDB0034675)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0034675)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034675)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	48.8 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.2	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.21 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034675

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013201

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751605

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside] (CFc000335783)

MOL for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

3D MOL for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

3D SDF for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

3D-SDF for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

PDB for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

3D PDB for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

SMILES for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

INCHI for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

Structure for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])

3D Structure for CFc000335783 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-[glucosyl-(1->4)-glucoside])