N-Acetyl-D-cysteine (YMDB00820)

Identification

YMDB ID

YMDB00820

Name

N-Acetyl-D-cysteine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-Acetyl-D-cysteine 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-D-cysteine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-cysteine may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

CAS number

26117-28-2

Weight

Average: 163.195
Monoisotopic: 163.030313849

InChI Key

PWKSKIMOESPYIA-SCSAIBSYSA-N

InChI

InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

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

Chemical Formula

C₅H₉NO₃S

SMILES

[H]OC(=O)[C@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])S[H]

Chemical Taxonomy

Description

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.

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-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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)	-1.5	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	15.45 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-13c710ac0e0547e1ec40	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-1900000000-1fd4ac48c9f822eb3500	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-6900000000-d0c51a69ac11096d05c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-218fead85424144539bd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-55d7f2c18d3e85caad05	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-6900000000-ceec8ba29592de7e4362	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9200000000-fca1bad01b5fff79588b	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Abe, T., Hashimoto, Y., Hosaka, H., Tomita-Yokotani, K., Kobayashi, M. (2008). "Discovery of amide (peptide) bond synthetic activity in Acyl-CoA synthetase." J Biol Chem 283:11312-11321.18305111
Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2006). "Physiological role of D-amino acid-N-acetyltransferase of Saccharomyces cerevisiae: detoxification of D-amino acids." Arch Microbiol 185:39-46.16362288

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	94364
Kegg ID	Not Available
ChemSpider ID	85162
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0xb3c72370>

Enzymes

Reactions