Showing Compound N-Acetyl-L-cysteine (FDB002281)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:18 UTC

Update date

2019-11-26 02:57:16 UTC

Primary ID

FDB002281

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetyl-L-cysteine

Description

Effective inhibitor of enzymic browning in foods [DFC] N-Acetyl-L-cysteine is a pharmaceutical drug and nutritional supplement used primarily as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. Other uses include sulfate repletion in conditions, such as autism, where cysteine and related sulfur amino acids may be depleted. N-Acetyl-L-cysteine is a precursor in the formation of the antioxidant glutathione in the body. The thiol group confers antioxidant effects and is able to reduce free radicals. [Wikipedia].

CAS Number

616-91-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
(2R)-2-(Acetylamino)-3-mercaptopropanoic acid	biospider
(2R)-2-Acetamido-3-sulfanyl-propanoic acid	biospider
(2R)-2-Acetylamino-3-sulfanylpropanoate	Generator
(2R)-2-acetylamino-3-Sulfanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulfanylpropanoic acid	ChEBI
(2R)-2-Acetylamino-3-sulphanylpropanoate	Generator
(2R)-2-acetylamino-3-Sulphanylpropanoate	Generator
(2R)-2-Acetylamino-3-sulphanylpropanoic acid	Generator
(2R)-2-acetylamino-3-Sulphanylpropanoic acid	Generator
(R)-2-Acetylamino-3-mercaptopropanoate	Generator

Showing 1 to 10 of 214 entries

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

Chemical Formula

C5H9NO3S

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

163.195

Monoisotopic Molecular Weight

163.030313849

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Cell and elements:

Cell:

Fibroblast

Tissue and substructures:

Placenta

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Antioxidant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	9.52
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 36.80%; H 5.56%; N 8.58%; O 29.41%; S 19.65%	DFC
Melting Point	Mp 109-110°	DFC
Optical Rotation	[a]D +5 (c, 3 in H2O)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	N-Acetyl-L-cysteine, 3 TMS, GC-MS Spectrum	splash10-0i00-2970000000-d817070e3a42f5e63ec5	Spectrum
GC-MS	N-Acetyl-L-cysteine, non-derivatized, GC-MS Spectrum	splash10-01ox-9000000000-192b8907b32f1e180c72	Spectrum
GC-MS	N-Acetyl-L-cysteine, non-derivatized, GC-MS Spectrum	splash10-0i00-2970000000-d817070e3a42f5e63ec5	Spectrum
Predicted GC-MS	N-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9300000000-13c710ac0e0547e1ec40	Spectrum
Predicted GC-MS	N-Acetyl-L-cysteine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0100-9400000000-f5d15a7328f8eeae70fe	Spectrum
Predicted GC-MS	N-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-L-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-b0d92bfcc2536077a6fc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-f305286cee84e6ae992b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-9000000000-b10b4a2a6383336db871	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-056u-9100000000-dee19b6f8563eed2051a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-193b1f4952acc2d05623	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05i0-9800000000-f7137c548e759655c43b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-9000000000-65dc0cf1be1f7faf55ae	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e55a53ec6cd33256625c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-1900000000-3e0a700d54f883459247	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-218c3634602dff3b0ef7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a6r-9000000000-2f5a099f36fbc10b636b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9000000000-139c43a5e4b22393c761	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-85cb2a9affac4a096836	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-cf25c215d3b2da99e302	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0229-3900000000-2b2f710043af50879a7a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9100000000-a3a7de05cec65f647848	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9100000000-47a9c1939aac577c2793	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9100000000-be087caed53fbf56c467	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-066r-9000000000-e49809cd4e6d92af0e53	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-1900000000-1fd4ac48c9f822eb3500	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-d0c51a69ac11096d05c3	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-218fead85424144539bd	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-55d7f2c18d3e85caad05	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-6900000000-ceec8ba29592de7e4362	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9200000000-fca1bad01b5fff79588b	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum