ChemFOnt: Showing chemical card for Cotinine glucuronide (CFc000000801)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:18 UTC

Chemfont ID

CFc000000801

Molecule Identification

Common Name

Cotinine glucuronide

Definition

Cotinineglucuronide is a natural human metabolite of Cotinine generated in the liver by UDP glucuonyltransferase. A cotinine derviative that is dervied through glucuronidation by UDP-glucuronosyltransferases (UGTs) in the liver. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-b-D-Glucopyranuronosyl-3-(1-methyl-5-oxo-2-pyrrolidinyl)- pyridinium	HMDB
1-beta-delta-Glucopyranuronosyl-3-(1-methyl-5-oxo-2-pyrrolidinyl)- pyridinium	HMDB
Cotinine-glucuronide	HMDB
Cotinine-N-glucuronide	HMDB

Chemical Formula

C₁₆H₂₀N₂O₇

Average Molecular Weight

352.3392

Monoisotopic Molecular Weight

352.127051004

IUPAC Name

1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-3-(1-methyl-5-oxopyrrolidin-2-yl)-1λ⁵-pyridin-1-ylium

Traditional Name

1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-3-(1-methyl-5-oxopyrrolidin-2-yl)-1λ⁵-pyridin-1-ylium

CAS Registry Number

139427-57-9

SMILES

CN1C(CCC1=O)C1=C[N+](=CC=C1)C1OC(C(O)C(O)C1O)C([O-])=O

InChI Identifier

InChI=1S/C16H20N2O7/c1-17-9(4-5-10(17)19)8-3-2-6-18(7-8)15-13(22)11(20)12(21)14(25-15)16(23)24/h2-3,6-7,9,11-15,20-22H,4-5H2,1H3

InChI Key

XWZCZWKUGIQPJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-glucuronides

Alternative Parents

Substituents

N-glucuronide
Glycosyl compound
N-glycosyl compound
Pyrrolidinylpyridine
Alkaloid or derivatives
Beta-hydroxy acid
Hydroxy acid
Oxane
Pyran
Pyridine
Pyridinium
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Carboxylic acid salt
Carboxamide group
Secondary alcohol
Lactam
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organic salt
Hydrocarbon derivative
Organonitrogen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-2747 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0001013)
Kidney (HMDB: HMDB0001013)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0001013)

Source

Endogenous

Endogenous (HMDB: HMDB0001013)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotine Metabolism Pathway (HMDB: HMDB0001013)
Nicotine Metabolism Pathway (PathBank: SMP0000628)

Drug action pathway

Nicotine Action Pathway (HMDB: HMDB0001013)
Nicotine Action Pathway (PathBank: SMP0000431)

Role

Biological role

Drug metabolite (HMDB: HMDB0001013)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.54 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-5.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.8 m³·mol⁻¹	ChemAxon
Polarizability	33.72 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