ChemFOnt: Showing chemical card for 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside (CFc000042786)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:29 UTC

Chemfont ID

CFc000042786

Molecule Identification

Common Name

4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside

Definition

4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside, also known as 4-AHPh-oba-glu, is classified as a member of the Phenolic glycosides. Phenolic glycosides 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. 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside is considered to be slightly soluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(2-Amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoate	Generator
4-(2-amino-3-Hydroxyphenyl)-4-oxobutanoate O-glucoside	Generator
4-AHPh-oba-glu	HMDB

Chemical Formula

C₁₆H₂₁NO₉

Average Molecular Weight

371.342

Monoisotopic Molecular Weight

371.12163126

IUPAC Name

4-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoic acid

Traditional Name

4-(2-amino-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@@]([H])(OC2=CC=CC(C(=O)CCC(O)=O)=C2N)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C16H21NO9/c17-12-7(8(19)4-5-11(20)21)2-1-3-9(12)25-16-15(24)14(23)13(22)10(6-18)26-16/h1-3,10,13-16,18,22-24H,4-6,17H2,(H,20,21)/t10-,13-,14+,15-,16-/m1/s1

InChI Key

XEXCWFKGYJFAQK-LMXXTMHSSA-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
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Butyrophenone
Phenylketone
Phenol ether
Aryl ketone
Aryl alkyl ketone
Phenoxy compound
Aniline or substituted anilines
Gamma-keto acid
Benzoyl
Oxane
Benzenoid
Monosaccharide
Keto acid
Monocyclic benzene moiety
Primary aromatic amine
Vinylogous amide
Amino acid or derivatives
Secondary alcohol
Ketone
Amino acid
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Aldehyde
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Primary amine
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062374)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	7.57 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	2.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.18 m³·mol⁻¹	ChemAxon
Polarizability	35.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

10948689

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside (CFc000042786)

MOL for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

3D MOL for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

3D SDF for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

3D-SDF for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

PDB for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

3D PDB for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

SMILES for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

INCHI for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

Structure for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)

3D Structure for CFc000042786 (4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside)