MiMeDB: Showing metabocard for Acetylcysteine (MMDBc0000396)

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:50 UTC

Update Date

2024-09-27 19:16:00 UTC

Metabolite ID

MMDBc0000396

Metabolite Identification

Common Name

Acetylcysteine

Description

N-Acetyl-L-cysteine (NAC) or N-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. N-Acetylcysteine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-cysteine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-cysteine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-cysteine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. . N-acetylated amino acids, such as N-acetylcysteine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free cysteine can also occur. The enzyme known as cysteine-S-conjugate N-acetyltransferase (EC 2.3.1.80) catalyzes the transfer of the acetyl group of acetyl CoA to the amino group of cysteine. This enzyme is an important participant in glutathione metabolism and the production of glutathione. The thiol (sulfhydryl) group in N-Acetylcysteine confers antioxidant effects and is able to reduce free radicals. N-Acetylcysteine is a pharmacological agent used in the management of paracetamol (acetaminophen) overdoses. When acetaminophen is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. NAPQI is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to deactivate the toxic NAPQI. In the treatment of acetaminophen overdose, N-acetylcysteine acts to maintain or replenish depleted glutathione reserves in the liver and enhance non-toxic metabolism of acetaminophen. These actions serve to protect liver cells from NAPQI toxicity. For this particular indication, N-acetylcysteine is available under the trade names Mucomyst (Bristol-Myers Squibb) and Parvolex (GSK). N-Acetylcysteine is also 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. Acetylcysteine has been studied for a number of psychiatric disorders. There is tentative evidence for N-acetylcysteine being useful in the treatment of Alzheimer's disease, autism, bipolar disorder, drug-induced neuropathy, major depressive disorder, obsessive-compulsive disorder, and schizophrenia (PMID: 21118657 ). Many N-acetylamino acids, including N-acetylcysteine, can act as uremic toxins if present in high abundance in the serum or plasma (PMID: 21970774 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₅H₉NO₃S

Average Mass

163.195

Monoisotopic Mass

163.030313849

IUPAC Name

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

Traditional Name

acetylcysteine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.09 g/L	ALOGPS
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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01ox-9000000000-192b8907b32f1e180c72	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0i00-2970000000-d817070e3a42f5e63ec5	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-13c710ac0e0547e1ec40	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0100-9400000000-f5d15a7328f8eeae70fe	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-b0d92bfcc2536077a6fc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-f305286cee84e6ae992b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-b10b4a2a6383336db871	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-056u-9100000000-dee19b6f8563eed2051a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-193b1f4952acc2d05623	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05i0-9800000000-f7137c548e759655c43b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-9000000000-65dc0cf1be1f7faf55ae	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e55a53ec6cd33256625c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-1900000000-3e0a700d54f883459247	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-218c3634602dff3b0ef7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a6r-9000000000-2f5a099f36fbc10b636b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9000000000-139c43a5e4b22393c761	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-85cb2a9affac4a096836	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-cf25c215d3b2da99e302	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-3900000000-2b2f710043af50879a7a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9100000000-a3a7de05cec65f647848	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9100000000-47a9c1939aac577c2793	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-be087caed53fbf56c467	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-066r-9000000000-e49809cd4e6d92af0e53	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-1900000000-1fd4ac48c9f822eb3500	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-d0c51a69ac11096d05c3	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-218fead85424144539bd	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-55d7f2c18d3e85caad05	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-6900000000-ceec8ba29592de7e4362	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9200000000-fca1bad01b5fff79588b	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	234.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	113.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	135.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	418.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	308.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	355.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1729.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	416.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	978.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	250.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	231.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	218.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	71.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	244.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	684.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	84.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	216.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1163.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	713.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Acetylcysteine_TMS_1	CC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1686.36
Gas Chromatography	Acetylcysteine_TMS_2	CC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2050.25
Gas Chromatography	Acetylcysteine_TMS_3	CC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1785.46
Gas Chromatography	Acetylcysteine_TMS_4	CC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1706.47
Gas Chromatography	Acetylcysteine_TMS_5	CC(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2378.77
Gas Chromatography	Acetylcysteine_TMS_6	CC(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	2273.24
Gas Chromatography	Acetylcysteine_TMS_7	CC(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1788.25
Gas Chromatography	Acetylcysteine_TMS_1	CC(=O)N[C@@H](CS)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2056.41
Gas Chromatography	Acetylcysteine_TMS_2	CC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2343.85
Gas Chromatography	Acetylcysteine_TMS_3	CC(=O)N([C@@H](CS)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	1947.02
Gas Chromatography	Acetylcysteine_TMS_4	CC(=O)N[C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2258.61
Gas Chromatography	Acetylcysteine_TMS_5	CC(=O)N([C@@H](CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2527.28
Gas Chromatography	Acetylcysteine_TMS_6	CC(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2293.56
Gas Chromatography	Acetylcysteine_TMS_7	CC(=O)N([C@@H](CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2045.28

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta
Urine

Tissue Locations

Fibroblasts
Intestine
Kidney
Liver
Neuron
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Actinobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	4.0	4.29	5.0	uM	Adult (>18 years old)	Both	Normal	HMDB	2026726
Human Urine	Detected and Quantified		0	0.13	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Great Plains Laboratory Reference Values (Males >13)
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27065191
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001890

DrugBank ID

DB06151

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002281

KNApSAcK ID

Not Available

Chemspider ID

11540

KEGG Compound ID

C06809

BioCyc ID

CPD-9175

BiGG ID

Not Available

Wikipedia Link

Acetylcysteine

METLIN ID

784

PubChem Compound

12035

PDB ID

Not Available

ChEBI ID

28939

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Dawson AH, Henry DA, McEwen J: Adverse reactions to N-acetylcysteine during treatment for paracetamol poisoning. Med J Aust. 1989 Mar 20;150(6):329-31. doi: 10.5694/j.1326-5377.1989.tb136496.x. [PubMed:2716644 ]
Hook GE, Gilmore LB, Talley FA: Dissolution and reassembly of tubular myelin-like multilamellated structures from the lungs of patients with pulmonary alveolar proteinosis. Lab Invest. 1986 Aug;55(2):194-208. [PubMed:3755483 ]
Bailey B, McGuigan MA: Management of anaphylactoid reactions to intravenous N-acetylcysteine. Ann Emerg Med. 1998 Jun;31(6):710-5. doi: 10.1016/s0196-0644(98)70229-x. [PubMed:9624310 ]
Jones AL: Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review. J Toxicol Clin Toxicol. 1998;36(4):277-85. doi: 10.3109/15563659809028022. [PubMed:9711192 ]
Langman M, Boyle P: Chemoprevention of colorectal cancer. Gut. 1998 Oct;43(4):578-85. doi: 10.1136/gut.43.4.578. [PubMed:9824590 ]
Breitkreutz R, Pittack N, Nebe CT, Schuster D, Brust J, Beichert M, Hack V, Daniel V, Edler L, Droge W: Improvement of immune functions in HIV infection by sulfur supplementation: two randomized trials. J Mol Med (Berl). 2000;78(1):55-62. doi: 10.1007/s001099900073. [PubMed:10759030 ]
Cereser C, Boget S, Parvaz P, Revol A: Thiram-induced cytotoxicity is accompanied by a rapid and drastic oxidation of reduced glutathione with consecutive lipid peroxidation and cell death. Toxicology. 2001 Jun 21;163(2-3):153-62. doi: 10.1016/s0300-483x(01)00401-2. [PubMed:11516525 ]
Weigand MA, Plachky J, Thies JC, Spies-Martin D, Otto G, Martin E, Bardenheuer HJ: N-acetylcysteine attenuates the increase in alpha-glutathione S-transferase and circulating ICAM-1 and VCAM-1 after reperfusion in humans undergoing liver transplantation. Transplantation. 2001 Aug 27;72(4):694-8. doi: 10.1097/00007890-200108270-00023. [PubMed:11544433 ]
Fulghesu AM, Ciampelli M, Muzj G, Belosi C, Selvaggi L, Ayala GF, Lanzone A: N-acetyl-cysteine treatment improves insulin sensitivity in women with polycystic ovary syndrome. Fertil Steril. 2002 Jun;77(6):1128-35. doi: 10.1016/s0015-0282(02)03133-3. [PubMed:12057717 ]
Soheili Majd E, Goldberg M, Stanislawski L: In vitro effects of ascorbate and Trolox on the biocompatibility of dental restorative materials. Biomaterials. 2003 Jan;24(1):3-9. doi: 10.1016/s0142-9612(02)00221-1. [PubMed:12417172 ]
Bachert C, Hormann K, Mosges R, Rasp G, Riechelmann H, Muller R, Luckhaupt H, Stuck BA, Rudack C: An update on the diagnosis and treatment of sinusitis and nasal polyposis. Allergy. 2003 Mar;58(3):176-91. doi: 10.1034/j.1398-9995.2003.02172.x. [PubMed:12653791 ]
Hein OV, Ohring R, Schilling A, Oellerich M, Armstrong VW, Kox WJ, Spies C: N-acetylcysteine decreases lactate signal intensities in liver tissue and improves liver function in septic shock patients, as shown by magnetic resonance spectroscopy: extended case report. Crit Care. 2004 Apr;8(2):R66-71. doi: 10.1186/cc2426. Epub 2004 Jan 22. [PubMed:15025780 ]
Lucena MI, Lopez-Torres E, Verge C, Andrade RJ, Puche MJ, Seoane J, de la Cuesta FS: The administration of N-acetylcysteine causes a decrease in prothrombin time in patients with paracetamol overdose but without evidence of liver impairment. Eur J Gastroenterol Hepatol. 2005 Jan;17(1):59-63. doi: 10.1097/00042737-200501000-00012. [PubMed:15647642 ]
Alscher DM, Braun N, Biegger D, Stuelten C, Gawronski K, Murdter TE, Kuhlmann U, Fritz P: Induction of metallothionein in proximal tubular cells by zinc and its potential as an endogenous antioxidant. Kidney Blood Press Res. 2005;28(3):127-33. doi: 10.1159/000084921. Epub 2005 Apr 5. [PubMed:15812196 ]
Wilkes JM, Clark LE, Herrera JL: Acetaminophen overdose in pregnancy. South Med J. 2005 Nov;98(11):1118-22. doi: 10.1097/01.smj.0000184792.15407.51. [PubMed:16351032 ]
Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. doi: 10.1086/500563. Epub 2006 Jan 18. [PubMed:16465618 ]
Faucet-Marquis V, Pont F, Stormer FC, Rizk T, Castegnaro M, Pfohl-Leszkowicz A: Evidence of a new dechlorinated ochratoxin A derivative formed in opossum kidney cell cultures after pretreatment by modulators of glutathione pathways: correlation with DNA-adduct formation. Mol Nutr Food Res. 2006 May;50(6):530-42. doi: 10.1002/mnfr.200500219. [PubMed:16671059 ]
Kramers C, Jansman FG, Droogleever Fortuyn H: [A patient who refused treatment after self-poisoning with paracetamol]. Ned Tijdschr Geneeskd. 2006 Jul 22;150(29):1601-4. [PubMed:16901061 ]
Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]
Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
Dean O, Giorlando F, Berk M: N-acetylcysteine in psychiatry: current therapeutic evidence and potential mechanisms of action. J Psychiatry Neurosci. 2011 Mar;36(2):78-86. doi: 10.1503/jpn.100057. [PubMed:21118657 ]
Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
Mullins ME, Vitkovitsky IV: Hemolysis and hemolytic uremic syndrome following five-fold N-acetylcysteine overdose. Clin Toxicol (Phila). 2011 Oct;49(8):755-9. doi: 10.3109/15563650.2011.609821. [PubMed:21970774 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]

Showing metabocard for Acetylcysteine (MMDBc0000396)

MOL for #<Metabolite:0x00007f9a9df30bd0>

3D MOL for #<Metabolite:0x00007f9a9df30bd0>

3D SDF for #<Metabolite:0x00007f9a9df30bd0>

3D-SDF for #<Metabolite:0x00007f9a9df30bd0>

PDB for #<Metabolite:0x00007f9a9df30bd0>

3D PDB for #<Metabolite:0x00007f9a9df30bd0>

SMILES for #<Metabolite:0x00007f9a9df30bd0>

INCHI for #<Metabolite:0x00007f9a9df30bd0>

Structure for #<Metabolite:0x00007f9a9df30bd0>

3D Structure for #<Metabolite:0x00007f9a9df30bd0>