ContaminantDB: Acetaminophen glucuronide

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:35:05 UTC

Update Date

2016-11-09 01:17:30 UTC

Accession Number

CHEM022442

Identification

Common Name

Acetaminophen glucuronide

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Paracetamol glucuronide	ChEBI
4-(Acetylamino)phenyl beta-D-glucopyranosiduronic acid	HMDB
4-(Acetylamino)phenyl beta-delta-glucopyranosiduronic acid	HMDB
4-Acetamidophenol glucuronide	HMDB
4-Acetamidophenyl b-D-glucopyranosiduronic acid	HMDB
4-Acetamidophenyl b-delta-glucopyranosiduronic acid	HMDB
4-Acetamidophenyl beta-D-glucopyranosiduronic acid	HMDB
4-Acetamidophenyl beta-delta-glucopyranosiduronic acid	HMDB
p-Acetamidophenyl β-D-glucuronide	HMDB
4-(Acetylamino)phenyl β-D-glucopyranosiduronic acid	HMDB
4-Glucuronosidoacetanilide	HMDB
4-Hydroxyacetanilide glucuronide	HMDB
Acetanilide glucuronide	HMDB
4'-(Glucuronosyloxy)-acetanilide	HMDB
Deethylphenacetin glucuronide	HMDB
N-Acetyl-4-aminophenol glucuronide	HMDB
N-Acetyl-4-glucuronosidoaniline	HMDB
N-Acetyl-p-aminophenyl glucuronide	HMDB
Paracetamol O-glucuronide	HMDB
Paracetamol β-glucuronide	HMDB
Paracetamol beta-glucuronide	HMDB
p-Acetamidophenyl D-glucosiduronic acid	HMDB
p-Acetamidophenyl glucosiduronic acid	HMDB
p-Acetamidophenyl glucuronide	HMDB
PCM-g	HMDB
p-Acetamidophenylglucuronide	HMDB
Acetaminophen glucuronide	HMDB

Chemical Formula

C₁₄H₁₇NO₈

Average Molecular Mass

327.287 g/mol

Monoisotopic Mass

327.095 g/mol

CAS Registry Number

16110-10-4

IUPAC Name

(2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

acetaminophen glucuronide

SMILES

CC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1

InChI Key

IPROLSVTVHAQLE-BYNIDDHOSA-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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Phenoxy compound
Phenol ether
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Monosaccharide
Benzenoid
Pyran
Oxane
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucosiduronic acid (CHEBI:32636 )

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	27.7 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.91 m³·mol⁻¹	ChemAxon
Polarizability	30.69 Å³	ChemAxon
Number of Rings	2	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9352000000-77fed48f2ac24b73fab8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0udi-4100349000-5176b6b37f6857b7f999	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03k9-0900000000-5e02cd6d491f4b1cf8f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00di-0900000000-acce7f7634727584b435	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0922000000-d3ea032d2b2a786b49a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-7bb565a0815d9e8681c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0w29-2900000000-8029b9ba6317a5c7bacb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1902000000-63bf36b7f8481253b041	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3901000000-ac725135cde5a222d64a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9800000000-d0386babb34ac3708373	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014l-9200000000-dc0cedc02a918704f9c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0udi-0907000000-cc6b4eeb1854a02b091e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ik9-2900000000-f45589acb1254525eedc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03di-4900000000-8f1b83b451250f90fa5f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0xxr-3900000000-560c53f10968963e3a63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0udi-0907000000-ab44d212f9ebe70f73e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0zfr-9800000000-16b1e116a6a82ae143a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-7900000000-0106d7d985bdfc7ce4ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0902000000-232646fdc95c354d8ef2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0901000000-24d1372940103501af9d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-6900000000-65f843147decea0cfc44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w4i-0946000000-4049f1415ff9576f5924	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0910000000-a1b732d82b46888499a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc0-2900000000-7fe5c0cbd17367744596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fc0-2968000000-a253cd8c945d814768e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2931000000-8678b1c192068d44639b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-3900000000-6e974e4924ffcc0ae778	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
1D NMR	1H 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

HMDB0010316

FooDB ID

FDB027468

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Beta-D-Glucuronides

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

75744

ChEBI ID

32636

PubChem Compound ID

83944

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Aw TY, Jones DP: Intracellular inhibition of UDP-glucose dehydrogenase during ethanol oxidation. Chem Biol Interact. 1983 Mar;43(3):283-8.

2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225

Acetaminophen glucuronide (CHEM022442)

Structure for CHEM022442: Acetaminophen glucuronide