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(R)-2-hydroxy-3-mercaptopropanoic acid

PubChem CID
9833951
Structure
(R)-2-hydroxy-3-mercaptopropanoic acid_small.png
(R)-2-hydroxy-3-mercaptopropanoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • L-3-Mercaptolactate
  • (R)-2-hydroxy-3-mercaptopropanoic acid
  • (2R)-2-hydroxy-3-sulfanylpropanoic acid
  • 3-Mercaptolactate
  • (R)-3-Mercaptolactate
Molecular Weight
122.15 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-18
Description
3-mercaptolactic acid is a (2R)-2-hydroxy monocarboxylic acid consisting of lactic acid having a sulfanyl group at the 3-position. It has a role as a mouse metabolite. It is a (2R)-2-hydroxy monocarboxylic acid and a thiol. It is a conjugate acid of a 3-mercaptolactate.
(R)-2-hydroxy-3-mercaptopropanoic acid has been reported in Homo sapiens, Bos taurus, and Euglena gracilis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(R)-2-hydroxy-3-mercaptopropanoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-hydroxy-3-sulfanylpropanoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C3H6O3S/c4-2(1-7)3(5)6/h2,4,7H,1H2,(H,5,6)/t2-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

OLQOVQTWRIJPRE-REOHCLBHSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C([C@@H](C(=O)O)O)S
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C3H6O3S
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 KEGG ID

2.3.3 Nikkaji Number

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-hydroxy-3-mercaptopropionic acid
  • 3-mercaptolactic acid
  • beta-mercaptolactate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
122.15 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
122.00376522 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
122.00376522 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
58.5 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
7
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
72.6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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 2010.01.29)

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Biochemical Reactions

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 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

8.5 Chemical-Gene Co-Occurrences in Patents

9 Interactions and Pathways

9.1 Pathways

10 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

11 Classification

11.1 MeSH Tree

11.2 ChEBI Ontology

11.3 LOTUS Tree

11.4 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    (R)-2-hydroxy-3-mercaptopropanoic acid
    https://www.wikidata.org/wiki/Q27103783
  3. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    3-mercaptolactic acid
  4. Natural Product Activity and Species Source (NPASS)
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. 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
  7. Wikidata
  8. PubChem
  9. 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
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  11. PATENTSCOPE (WIPO)
CONTENTS