Livestock Metabolome Database: Showing metabocard for Acetylcysteine (LMDB00363)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:10 UTC

Update Date

2016-07-20 21:00:12 UTC

Lmdb

LMDB00363

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetylcysteine

Description

Acetylcysteine is the N-acetyl derivative of the amino acid L-cysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals. wikipedia. It is used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. -- Pubchem. Acetylcysteine is a pharmacological agent used in the management of paracetamol overdose. For these indications, acetylcysteine is available under the trade names Mucomyst (Bristol-Myers Squibb) and Parvolex (GSK.-- Wikipedia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Acetylamino-3-sulfanylpropanoic acid	ChEBI
(R)-2-Acetylamino-3-mercaptopropanoic acid	ChEBI
(R)-Mercapturic acid	ChEBI
Acetilcisteina	ChEBI
Acetylcysteinum	ChEBI
L-Acetylcysteine	ChEBI
L-alpha-Acetamido-beta-mercaptopropionic acid	ChEBI
Mercapturic acid	ChEBI
N-Acetyl-L-(+)-cysteine	ChEBI
N-Acetylcysteine	ChEBI
NAC	ChEBI
(2R)-2-Acetylamino-3-sulfanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulphanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulphanylpropanoic acid	Generator
(R)-2-Acetylamino-3-mercaptopropanoate	Generator
(R)-Mercaptate	Generator
(R)-Mercaptic acid	Generator
L-a-Acetamido-b-mercaptopropionate	Generator
L-a-Acetamido-b-mercaptopropionic acid	Generator
L-alpha-Acetamido-beta-mercaptopropionate	Generator
L-Α-acetamido-β-mercaptopropionate	Generator
L-Α-acetamido-β-mercaptopropionic acid	Generator
Mercaptate	Generator
Mercaptic acid	Generator
Acetadote	HMDB
Flumucetin	HMDB
2-acetylamino-3-mercapto-Propionate	HMDB
2-acetylamino-3-mercapto-Propionic acid	HMDB
Fluimicil infantil	HMDB
Fluimucetin	HMDB
Fluprowit	HMDB, MeSH
N-Acety-L-cysteine	HMDB
N-Acetyl-3-mercaptoalanine	HMDB
Sodium 2-acetamido-3-mercaptopropionate	HMDB
Acemuc	MeSH, HMDB
Acetylcysteine alcon brand	MeSH, HMDB
Acetylcysteine betapharm brand	MeSH, HMDB
Acetylcysteine bouchara brand	MeSH, HMDB
Acetylcysteine farmasan brand	MeSH, HMDB
Acetylcysteine fresenius brand	MeSH, HMDB
Acetylcysteine inpharzam brand	MeSH, HMDB
Acetylcysteine klinge brand	MeSH, HMDB
Acetylcysteine lindopharm brand	MeSH, HMDB
Acetylcysteine pharbita brand	MeSH, HMDB
Acetylcysteine whitehall brand	MeSH, HMDB
Acetylcysteine, monosodium salt	MeSH, HMDB
Acétylcystéine GNR	MeSH, HMDB
Allen and hanburys brand OF acetylcysteine	MeSH, HMDB
Bioiberica brand OF acetylcysteine	MeSH, HMDB
Bristol myers squibb brand OF acetylcysteine	MeSH, HMDB
Bromuc	MeSH, HMDB
Dey brand OF acetylcysteine sodium salt	MeSH, HMDB
Eurespiran	MeSH, HMDB
Exomuc	MeSH, HMDB
Fresenius brand OF acetylcysteine	MeSH, HMDB
GNR Pharma brand OF acetylcysteine	MeSH, HMDB
GNR-Pharma brand OF acetylcysteine	MeSH, HMDB
Genac	MeSH, HMDB
Génévrier brand OF acetylcysteine	MeSH, HMDB
Hermes brand OF acetylcysteine	MeSH, HMDB
Heumann brand OF acetylcysteine	MeSH, HMDB
Monosodium salt acetylcysteine	MeSH, HMDB
Mucosil	MeSH, HMDB
NAC al	MeSH, HMDB
NAC, bisolvon	MeSH, HMDB
Oberlin brand OF acetylcysteine	MeSH, HMDB
Pfleger brand OF acetylcysteine	MeSH, HMDB
Produpharm lappe brand OF acetylcysteine	MeSH, HMDB
Roberts brand OF acetylcysteine	MeSH, HMDB
Roche nicholas brand OF acetylcysteine	MeSH, HMDB
Siran	MeSH, HMDB
Sodium, acetylcysteine	MeSH, HMDB
Temmler brand OF acetylcysteine	MeSH, HMDB
Teva brand OF acetylcysteine	MeSH, HMDB
Zambon brand OF acetylcysteine	MeSH, HMDB
Zambon, nac	MeSH, HMDB
Acetylcystein atid	MeSH, HMDB
Acetylcystein, mentopin	MeSH, HMDB
Acetylcysteine azupharma brand	MeSH, HMDB
Acetylcysteine centrafarm brand	MeSH, HMDB
Acetylcysteine hermes brand	MeSH, HMDB
Acetylcysteine krewel brand	MeSH, HMDB
Acetylcysteine temmler brand	MeSH, HMDB
Acetylcysteine teva brand	MeSH, HMDB
Acetylcysteine upsa brand	MeSH, HMDB
Acetylcysteine zyma brand	MeSH, HMDB
Acetylcysteine, (DL)-isomer	MeSH, HMDB
Betapharm brand OF acetylcysteine	MeSH, HMDB
Bristol myers squibb brand OF acetylcysteine sodium salt	MeSH, HMDB
Disphar brand OF acetylcysteine	MeSH, HMDB
Farmasan brand OF acetylcysteine	MeSH, HMDB
Fluimucil	MeSH, HMDB
Jenapharm	MeSH, HMDB
Klinge brand OF acetylcysteine	MeSH, HMDB
Lindopharm brand OF acetylcysteine	MeSH, HMDB
MPectil	MeSH, HMDB
Merck brand OF acetylcysteine	MeSH, HMDB
Mucosol	MeSH, HMDB
NAC zambon	MeSH, HMDB
Siccoral	MeSH, HMDB
Trommsdorff brand OF acetylcysteine	MeSH, HMDB
Zyma brand OF acetylcysteine	MeSH, HMDB
Mentopin acetylcystein	MeSH, HMDB
Acetylcystein al	MeSH, HMDB
Acetylcystein heumann	MeSH, HMDB
Acetylcystein trom	MeSH, HMDB
Acetylcysteine aluid brand	MeSH, HMDB
Acetylcysteine disphar brand	MeSH, HMDB
Acetylcysteine GNR-pharma brand	MeSH, HMDB
Acetylcysteine lichtenstein brand	MeSH, HMDB
Acetylcysteine merck brand	MeSH, HMDB
Acetylcysteine oberlin brand	MeSH, HMDB
Acetylcysteine roberts brand	MeSH, HMDB
Acetylcysteine sodium	MeSH, HMDB
Acetylcysteine thiemann brand	MeSH, HMDB
Acetylcysteine zinc	MeSH, HMDB
Acetylcysteine, monoammonium salt	MeSH, HMDB
Acetyst	MeSH, HMDB
Acid, mercapturic	MeSH, HMDB
Airbron	MeSH, HMDB
Alcon brand OF acetylcysteine	MeSH, HMDB
Aluid brand OF acetylcysteine	MeSH, HMDB
Alveolex	MeSH, HMDB
Atid brand OF acetylcysteine	MeSH, HMDB
Azubronchin	MeSH, HMDB
Boehringer ingelheim brand OF acetylcysteine	MeSH, HMDB
Bristol-myers squibb brand OF acetylcysteine sodium salt	MeSH, HMDB
broncho Fips	MeSH, HMDB
Broncholysin	MeSH, HMDB
Centrafarm brand OF acetylcysteine	MeSH, HMDB
Codotussyl	MeSH, HMDB
Cystamucil	MeSH, HMDB
dampo Mucopect	MeSH, HMDB
Hoestil	MeSH, HMDB
Hustengetränk, optipect	MeSH, HMDB
Inpharzam brand OF acetylcysteine	MeSH, HMDB
Intra brand OF acetylcysteine	MeSH, HMDB
Larylin nac	MeSH, HMDB
Lindocetyl	MeSH, HMDB
m Pectil	MeSH, HMDB
Mucopect, dampo	MeSH, HMDB
Mucosolvin	MeSH, HMDB
Optipect hustengetränk	MeSH, HMDB
Sanigen, muco	MeSH, HMDB
Solmucol	MeSH, HMDB
Thiemann brand OF acetylcysteine	MeSH, HMDB
Whitehall brand OF acetylcysteine	MeSH, HMDB
Zinc, acetylcysteine	MeSH, HMDB
Acebraus	MeSH, HMDB
Durabronchal	MeSH, HMDB
Acetabs	MeSH, HMDB
Acetylcysteine atid brand	MeSH, HMDB
Acetylcysteine bioiberica brand	MeSH, HMDB
Acetylcysteine guerbet brand	MeSH, HMDB
Acetylcysteine génévrier brand	MeSH, HMDB
Acetylcysteine heumann brand	MeSH, HMDB
Acetylcysteine hydrochloride	MeSH, HMDB
Acetylcysteine intra brand	MeSH, HMDB
Acetylcysteine pfleger brand	MeSH, HMDB
Acetylcysteine trommsdorff brand	MeSH, HMDB
Acetylcysteine zambon brand	MeSH, HMDB
Acetylcysteine ac-pharma brand	MeSH, HMDB
Acetylcysteine, (D)-isomer	MeSH, HMDB
Acetylin	MeSH, HMDB
Azupharma brand OF acetylcysteine	MeSH, HMDB
Bisolvon nac	MeSH, HMDB
Bouchara brand OF acetylcysteine	MeSH, HMDB
Bristol-myers squibb brand OF acetylcysteine	MeSH, HMDB
broncho-Fips	MeSH, HMDB
BronchoFips	MeSH, HMDB
Broncoclar	MeSH, HMDB
Fabrol	MeSH, HMDB
Frekatuss	MeSH, HMDB
Guerbet brand OF acetylcysteine	MeSH, HMDB
Hydrochloride, acetylcysteine	MeSH, HMDB
Ilube	MeSH, HMDB
Jenacystein	MeSH, HMDB
Krewel brand OF acetylcysteine	MeSH, HMDB
Lantamed	MeSH, HMDB
Lichtenstein brand OF acetylcysteine	MeSH, HMDB
m-Pectil	MeSH, HMDB
Monoammonium salt acetylcysteine	MeSH, HMDB
Muciteran	MeSH, HMDB
muco Sanigen	MeSH, HMDB
Mucomyst	MeSH, HMDB
N Acetyl L cysteine	MeSH, HMDB
N Acetylcysteine	MeSH, HMDB
Pharbita brand OF acetylcysteine	MeSH, HMDB
UPSA brand OF acetylcysteine	MeSH, HMDB
Ac pharma brand OF acetylcysteine	MeSH, HMDB
Ac-pharma brand OF acetylcysteine	MeSH, HMDB
Acetylcysteine	ChEBI

Chemical Formula

C₅H₉NO₃S

Average Molecular Weight

163.195

Monoisotopic Molecular Weight

163.030313849

IUPAC Name

(2R)-2-acetamido-3-sulfanylpropanoic acid

Traditional Name

acetylcysteine

CAS Registry Number

616-91-1

SMILES

CC(=O)N[C@@H](CS)C(O)=O

InChI Identifier

InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1

InChI Key

PWKSKIMOESPYIA-BYPYZUCNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-cysteine derivative (CHEBI:28939 )
N-acetyl-L-amino acid (CHEBI:28939 )
acetylcysteine (CHEBI:28939 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.03	ALOGPS
logP	-0.71	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37.67 m³·mol⁻¹	ChemAxon
Polarizability	15.34 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ox-9000000000-192b8907b32f1e180c72	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-13c710ac0e0547e1ec40	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9400000000-f5d15a7328f8eeae70fe	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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-b0d92bfcc2536077a6fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-f305286cee84e6ae992b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-b10b4a2a6383336db871	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-056u-9100000000-dee19b6f8563eed2051a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-193b1f4952acc2d05623	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05i0-9800000000-f7137c548e759655c43b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-9000000000-65dc0cf1be1f7faf55ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e55a53ec6cd33256625c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-1900000000-3e0a700d54f883459247	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-218c3634602dff3b0ef7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a6r-9000000000-2f5a099f36fbc10b636b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9000000000-139c43a5e4b22393c761	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-85cb2a9affac4a096836	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-cf25c215d3b2da99e302	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-3900000000-2b2f710043af50879a7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9100000000-a3a7de05cec65f647848	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9100000000-47a9c1939aac577c2793	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-be087caed53fbf56c467	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-066r-9000000000-e49809cd4e6d92af0e53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-1900000000-1fd4ac48c9f822eb3500	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-d0c51a69ac11096d05c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-218fead85424144539bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-55d7f2c18d3e85caad05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-6900000000-ceec8ba29592de7e4362	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9200000000-fca1bad01b5fff79588b	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
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details