An official website of the United States government

Procysteine

PubChem CID
72390
Structure
Procysteine_small.png
Procysteine_3D_Structure.png
Molecular Formula
Synonyms
  • Procysteine
  • 19771-63-2
  • oxothiazolidinecarboxylic acid
  • (R)-2-Oxothiazolidine-4-carboxylic acid
  • (4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid
Molecular Weight
147.15 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-01
  • Modify:
    2024-12-28
Description
(4R)-2-oxo-4-thiazolidinecarboxylic acid is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Procysteine has been used in trials studying the treatment of HIV Infections.
PROCYSTEINE is a small molecule drug with a maximum clinical trial phase of II and has 1 investigational indication.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Procysteine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

BMLMGCPTLHPWPY-REOHCLBHSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1[C@H](NC(=O)S1)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

C4H5NO3S
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

163675-62-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-oxo-4-thiazolidine carboxylic acid
  • 2-oxothiazolidine-4-carboxylate
  • 2-oxothiazolidine-4-carboxylic acid
  • 2-oxothiazolidine-4-carboxylic acid, (R)-isomer
  • 2-oxothiazolidine-4-carboxylic acid, (S)-isomer
  • L-2-OTZD-4-CXA
  • L-2-oxothiazolidine-4-carboxylate
  • oxothiazolidinecarboxylic acid
  • Procysteine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
147.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
-0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
146.99901420 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
146.99901420 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
91.7Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
9
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
158
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
302023
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
302023
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-52
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

102 99.99

103 24.70

101 13.90

73 8.50

148 8

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.2 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
145.9905
Instrument
Thermo Q Exactive HF
Instrument Type
LC-ESI-QFT
Ionization Mode
negative
Collision Energy
HCD (NCE 20-30-40%)
Retention Time
6.481667
Top 5 Peaks

102.98455 100

145.99048 25.32

58.99471 8.98

102.00053 6.97

121.09254 4.95

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
145.9914
Instrument
SCIEX TripleTOF 6600
Instrument Type
LC-ESI-QTOF
Ionization Mode
negative
Collision Energy
35 eV
Retention Time
6.22625
Top 5 Peaks

102.98042 42

77.36985 36

Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
T1223
Lot Number
FIE01-CRTF
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
302023
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
T1223
Lot Number
FIE01-CRTF
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
302023
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
T1223
Lot Number
FIE01-CRTF
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (97.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (97.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (97.4%)

Eye Irrit. 2 (97.4%)

STOT SE 3 (97.4%)

9 Toxicity

9.1 Toxicological Information

9.1.1 Acute Effects

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 ChEMBL Target Tree

15.5 UN GHS Classification

15.6 NORMAN Suspect List Exchange Classification

15.7 EPA DSSTox Classification

15.8 MolGenie Organic Chemistry Ontology

16 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    Oxothiazolidinecarboxylic acid
    https://www.drugbank.ca/drugs/DB12224
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. 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
  7. ChEBI
    (4R)-2-oxo-4-thiazolidinecarboxylic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:125673
  8. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  9. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  11. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
    2-oxothiazolidine-4-carboxylic acid
    https://ctdbase.org/detail.go?type=chem&acc=C029536
  12. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  13. Therapeutic Target Database (TTD)
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  16. Metabolomics Workbench
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Procysteine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. SpectraBase
    L-2-Thiazolidinone-4-carboxylic acid
    https://spectrabase.com/spectrum/4YYOKtaCBlA
    L-2-Thiazolidinone-4-carboxylic acid
    https://spectrabase.com/spectrum/6IKJGrqkYB7
    (-)-2-Oxo-4-thiazolidinecarboxylic acid
    https://spectrabase.com/spectrum/6Pae0gTVHZm
    L-2-Thiazolidinone-4-carboxylic acid
    https://spectrabase.com/spectrum/9tU49vh0WjW
    (-)-2-Oxo-4-thiazolidinecarboxylic acid
    https://spectrabase.com/spectrum/3RSiopt6sb8
    (-)-2-Oxo-4-thiazolidinecarboxylic acid
    https://spectrabase.com/spectrum/LSJV7Rmb2l7
    (-)-2-Oxo-4-thiazolidinecarboxylic acid
    https://spectrabase.com/spectrum/9mmFs74eBse
  19. Springer Nature
  20. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  21. Wikidata
    oxothiazolidinecarboxylic acid
    https://www.wikidata.org/wiki/Q27216284
  22. PubChem
  23. 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
    2-oxothiazolidine-4-carboxylic acid
    https://www.ncbi.nlm.nih.gov/mesh/67029536
  24. GHS Classification (UNECE)
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS