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N-Acetyl-S-(2-hydroxyethyl)-L-cysteine

PubChem CID
108009
Structure
N-Acetyl-S-(2-hydroxyethyl)-L-cysteine_small.png
N-Acetyl-S-(2-hydroxyethyl)-L-cysteine_3D_Structure.png
Molecular Formula
Synonyms
  • N-Acetyl-S-(2-hydroxyethyl)-L-cysteine
  • 15060-26-1
  • (2R)-2-acetamido-3-(2-hydroxyethylsulfanyl)propanoic acid
  • 2-Hydroxyethylmercapturic acid
  • L-Cysteine, N-acetyl-S-(2-hydroxyethyl)-
Molecular Weight
207.25 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2024-12-28
Description
S-(2-Hydroxyethyl)-N-acetyl-L-cysteine is a N-acyl-amino acid.
N-Acetyl-S-(2-Hydroxyethyl)Cysteine is a modified form of acetylcysteine that is a metabolite of ethylene oxide and may be found in the urine of smokers.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-Acetyl-S-(2-hydroxyethyl)-L-cysteine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Ac-Cys(EtOH)(EtOH)-OH
Sequence
X
HELM
PEPTIDE1{[ac].[*N[C@@H](CSCCO)C(=O)O |$_R1;;;;;;;;;;$|]}$$$$

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2R)-2-acetamido-3-(2-hydroxyethylsulfanyl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C7H13NO4S/c1-5(10)8-6(7(11)12)4-13-3-2-9/h6,9H,2-4H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

NAYOYSKSFGMFOB-LURJTMIESA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

CC(=O)N[C@@H](CSCCO)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

3.2 Molecular Formula

C7H13NO4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

19179-72-7
97170-09-7

3.3.2 UNII

3.3.3 ChEBI ID

3.3.4 DSSTox Substance ID

3.3.5 KEGG ID

3.3.6 Metabolomics Workbench ID

3.3.7 NCI Thesaurus Code

3.3.8 Nikkaji Number

3.3.9 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 2-hydroxyethylmercapturic acid
  • N-acetyl-S-(2-hydroxyethyl)cysteine
  • N-acetyl-S-(2-hydroxyethyl)cysteine, (L)-isomer
  • N-acetyl-S-2-hydroxyethyl-L-cysteine
  • S-(beta-hydroxyethyl)mercapturic acid

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
207.25 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
207.05652907 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
207.05652907 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
112Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
185
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Springer Nature References

7.4 Chemical Co-Occurrences in Literature

7.5 Chemical-Gene Co-Occurrences in Literature

7.6 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

9 Classification

9.1 MeSH Tree

9.2 NCI Thesaurus Tree

9.3 ChEBI Ontology

9.4 ChemIDplus

9.5 EPA DSSTox Classification

9.6 MolGenie Organic Chemistry Ontology

10 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    N-Acetyl-S-(2-hydroxyethyl)-L-cysteine
    https://commonchemistry.cas.org/detail?cas_rn=15060-26-1
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    N-Acetyl-S-(2-hydroxyethyl)-L-cysteine
    https://comptox.epa.gov/dashboard/DTXSID00914077
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. ChEBI
  6. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  9. Metabolomics Workbench
  10. Springer Nature
  11. Wikidata
    N-acetyl-S-(2-hydroxyethyl)-L-cysteine
    https://www.wikidata.org/wiki/Q27116339
  12. PubChem
  13. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    N-acetyl-S-(2-hydroxyethyl)cysteine
    https://www.ncbi.nlm.nih.gov/mesh/67031104
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  15. PATENTSCOPE (WIPO)
  16. NCBI
CONTENTS