ContaminantDB: trans-3-Hydroxycotinine glucuronide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:37:57 UTC

Update Date

2016-11-09 01:17:31 UTC

Accession Number

CHEM022509

Identification

Common Name

trans-3-Hydroxycotinine glucuronide

Class

Small Molecule

Description

3-Hydroxycotinine (3HC) is the main nicotine metabolite detected in smokers urine. It is also excreted as a glucuronide conjugate (3HC-Gluc). 3HC and trans-3-Hydroxycotinine glucuronide account for 40-60% of the nicotine dose in urine.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3'-Hydroxycotnine-glucuronide	HMDB
3HC-Gluc	HMDB
trans-3-Hydroxycotinine-glucuronide	HMDB

Chemical Formula

C₁₆H₂₀N₂O₈

Average Molecular Mass

368.339 g/mol

Monoisotopic Mass

368.122 g/mol

CAS Registry Number

132929-88-5

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid

SMILES

[H][C@@]1(O[C@@H]2CC(N(C)C2=O)C2=CC=CN=C2)O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8?,9-,10+,11+,12-,13+,16-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	38.9 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.3	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	149.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.01 m³·mol⁻¹	ChemAxon
Polarizability	35.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9073000000-a76eb98dd2fd62dd0584	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0006-4201179000-9254404b076d74eeae1c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mo-0905000000-7038294c68496223be60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0900000000-e54057ee0f0d26f3f378	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ac-1900000000-00b8bf1411dcaf0caf62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00r6-2907000000-30422e965692a971b41a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1902000000-11066820c76bbb6636dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06wd-4900000000-4188e8db1462ca96d24e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-f1fda6b1d975224b623d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0903000000-05352da20e71cb23d0ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1900000000-a1583b9a514b1fe49564	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0409000000-4e639ab1f3da97839083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05bf-4903000000-0beee16561bfd1bc86f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdl-5910000000-1226b09b79453fef7cb4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001204

FooDB ID

FDB022490

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6080

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

53477725

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Rop PP, Grimaldi F, Oddoze C, Viala A: Determination of nicotine and its main metabolites in urine by high-performance liquid chromatography. J Chromatogr. 1993 Feb 26;612(2):302-9.

trans-3-Hydroxycotinine glucuronide (CHEM022509)

Structure for CHEM022509: trans-3-Hydroxycotinine glucuronide