ChemFOnt: Showing chemical card for (2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid (CFc000223122)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:44:30 UTC

Chemfont ID

CFc000223122

Molecule Identification

Common Name

(2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid

Definition

(2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Based on a literature review very few articles have been published on (2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4S,5R,6R)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2R)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₅NO₁₁

Average Molecular Weight

467.427

Monoisotopic Molecular Weight

467.142760629

IUPAC Name

5-acetamido-4-hydroxy-2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

Traditional Name

methylumbelliferyl sialic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC1C(O)CC(OC2=CC3=C(C=C2)C(C)=CC(=O)O3)(OC1C(O)C(O)CO)C(O)=O

InChI Identifier

InChI=1S/C21H25NO11/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30)

InChI Key

KKDWIUJBUSOPGC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin-7-o-glycoside
Coumarin o-glycoside
N-acylneuraminic acid
N-acylneuraminic acid or derivatives
Neuraminic acid
C-glucuronide
C-glycosyl compound
Phenoxyacetate
Glycosyl compound
Benzopyran
1-benzopyran
Ketal
Pyranone
Oxane
Pyran
Benzenoid
Acetamide
Heteroaromatic compound
Carboxamide group
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Primary alcohol
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.88 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-1.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.81 m³·mol⁻¹	ChemAxon
Polarizability	44.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0243586

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3278768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4063354

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid (CFc000223122)

MOL for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

3D MOL for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

3D SDF for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

3D-SDF for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

PDB for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

3D PDB for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

SMILES for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

INCHI for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

Structure for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)

3D Structure for CFc000223122 ((2s,4s,5r,6r)-5-Acetamido-4-hydroxy-2-(4-methyl-2-oxo-chromen-7-yl)oxy-6-[(2r)-1,2,3-trihydroxypropyl]tetrahydropyran-2-carboxylic acid)