ChemFOnt: Showing chemical card for 4-O-(Indole-3-acetyl)-D-glucopyranose (CFc000281301)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:33 UTC

Chemfont ID

CFc000281301

Molecule Identification

Common Name

4-O-(Indole-3-acetyl)-D-glucopyranose

Definition

4-o-(indole-3-acetyl)-d-glucopyranose, also known as indole-3-acetyl-beta-1-D-glucose or B-D-glucopyranose, 1-(1h-indole-3-acetic acid), belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 4-o-(indole-3-acetyl)-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-o-(indole-3-acetyl)-d-glucopyranose can be found in corn, which makes 4-o-(indole-3-acetyl)-d-glucopyranose a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-(indol-3-yl)Acetyl-beta-D-glucose	ChEBI
1-O-(Indole-3-acetyl)-beta-1-D-glucose	ChEBI
1-O-indol-3-Ylacetyl-beta-D-glucose	ChEBI
1-O-indol-3-Ylacetylglucose	ChEBI
beta-D-Glucopyranose, 1-(1H-indole-3-acetate)	ChEBI
Iaa-glucose	ChEBI
Indole-3-acetic acid beta-D-glucoside	ChEBI
Indole-3-acetyl-beta-1-D-glucose	ChEBI
Indole-3-acetyl-beta-1-D-glucoside	ChEBI
1-O-(indol-3-yl)Acetyl-b-D-glucose	Generator
1-O-(indol-3-yl)Acetyl-β-D-glucose	Generator
1-O-(Indole-3-acetyl)-b-1-D-glucose	Generator
1-O-(Indole-3-acetyl)-β-1-D-glucose	Generator
1-O-indol-3-Ylacetyl-b-D-glucose	Generator
1-O-indol-3-Ylacetyl-β-D-glucose	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetate)	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
beta-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetate)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Indole-3-acetate b-D-glucoside	Generator
Indole-3-acetate beta-D-glucoside	Generator
Indole-3-acetate β-D-glucoside	Generator
Indole-3-acetic acid b-D-glucoside	Generator
Indole-3-acetic acid β-D-glucoside	Generator
Indole-3-acetyl-b-1-D-glucose	Generator
Indole-3-acetyl-β-1-D-glucose	Generator
Indole-3-acetyl-b-1-D-glucoside	Generator
Indole-3-acetyl-β-1-D-glucoside	Generator
1-O-(indol-3-Ylacetyl)-b-D-glucose	Generator
1-O-(indol-3-Ylacetyl)-β-D-glucose	Generator

Chemical Formula

C₁₆H₁₉NO₇

Average Molecular Weight

337.3246

Monoisotopic Molecular Weight

337.116151967

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate

Traditional Name

iaa-glucose

CAS Registry Number

52703-89-6

SMILES

OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2/t11-,13-,14+,15-,16+/m1/s1

InChI Key

HHDMMUWDSFASNB-JZYAIQKZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
Hexose monosaccharide
3-alkylindole
Indole
Monosaccharide
Oxane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl carbohydrate (CHEBI:17990 )
indoleacetic acid ester conjugate (CHEBI:17990 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301785)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.62 g/L	ALOGPS
logP	0.02	ALOGPS
logP	-0.56	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.88 m³·mol⁻¹	ChemAxon
Polarizability	31.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301785

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030935

KNApSAcK ID

Not Available

Chemspider ID

389235

KEGG Compound ID

C04197

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17990

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-O-(Indole-3-acetyl)-D-glucopyranose (CFc000281301)

MOL for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D MOL for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D SDF for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D-SDF for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

PDB for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D PDB for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

SMILES for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

INCHI for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

Structure for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D Structure for CFc000281301 (4-O-(Indole-3-acetyl)-D-glucopyranose)