ChemFOnt: Showing chemical card for (3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000226862)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:51:27 UTC

Chemfont ID

CFc000226862

Molecule Identification

Common Name

(3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

(3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, also known as furosemide glucuronide, belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Based on a literature review very few articles have been published on (3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylate	Generator
(3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulphamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylate	Generator
(3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulphamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator
6-(4-Chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
6-(4-Chloro-2-{[(furan-2-yl)methyl]amino}-5-sulphamoylbenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
6-(4-Chloro-2-{[(furan-2-yl)methyl]amino}-5-sulphamoylbenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	HMDB
Furosemide glucuronide	HMDB
Furosemide acyl glucuronide	HMDB
Furosemide glucuronate	HMDB

Chemical Formula

C₁₈H₁₉ClN₂O₁₁S

Average Molecular Weight

506.86

Monoisotopic Molecular Weight

506.0398083

IUPAC Name

6-(4-chloro-2-{[(furan-2-yl)methyl]amino}-5-sulfamoylbenzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{4-chloro-2-[(furan-2-ylmethyl)amino]-5-sulfamoylbenzoyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

NS(=O)(=O)C1=CC(C(=O)OC2OC(C(O)C(O)C2O)C(O)=O)=C(NCC2=CC=CO2)C=C1Cl

InChI Identifier

InChI=1S/C18H19ClN2O11S/c19-9-5-10(21-6-7-2-1-3-30-7)8(4-11(9)33(20,28)29)17(27)32-18-14(24)12(22)13(23)15(31-18)16(25)26/h1-5,12-15,18,21-24H,6H2,(H,25,26)(H2,20,28,29)

InChI Key

RNVHHPUYELVHRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Hexose monosaccharide
Aminobenzenesulfonamide
Aminobenzoic acid or derivatives
Benzenesulfonamide
Benzoate ester
4-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzenesulfonyl group
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Beta-hydroxy acid
Chlorobenzene
Halobenzene
Aralkylamine
Secondary aliphatic/aromatic amine
Aryl chloride
Hydroxy acid
Monosaccharide
Dicarboxylic acid or derivatives
Organosulfonic acid amide
Benzenoid
Oxane
Monocyclic benzene moiety
Pyran
Aryl halide
Vinylogous amide
Furan
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Amino acid
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid
Acetal
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Secondary amine
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Amine
Organopnictogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organosulfur compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.72 g/L	ALOGPS
logP	0.63	ALOGPS
logP	0.00061	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.85 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.77 m³·mol⁻¹	ChemAxon
Polarizability	45.95 Å³	ChemAxon
Number of Rings	3	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

HMDB0247326

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22378832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73744518

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000226862)

MOL for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000226862 ((3R,4S,5S,6S)-6-[4-Chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid)