Milk Composition Database: Showing metabocard for Acetylcysteine (BMDB0001890)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:48:39 UTC

Update Date

2020-06-04 20:22:20 UTC

MCDB ID

BMDB0001890

Secondary Accession Numbers

BMDB01890

Metabolite Identification

Common Name

Acetylcysteine

Description

Acetylcysteine, also known as NAC or (R)-mercaptate, 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. Acetylcysteine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. In cattle, acetylcysteine is involved in the metabolic pathway called the cysteine metabolism pathway.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	109.5 °C	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	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	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)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29565828	details

External Links

HMDB ID

HMDB0001890

DrugBank ID

DB06151

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Showing metabocard for Acetylcysteine (BMDB0001890)

Structure for BMDB0001890 (Acetylcysteine)