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Hawkinsin

PubChem CID
173909
Structure
Hawkinsin_small.png
Hawkinsin_3D_Structure.png
Molecular Formula
Synonyms
  • Hawkinsin
  • 63224-90-8
  • (2-L-Cystein-S-yl-1,4-dihydroxycyclohex-5-en-1-yl)acetic acid
  • CHEBI:149584
  • 2-Cyclohexene-1-acetic acid, 6-((2-amino-2-carboxyethyl)thio)-1,4-dihydroxy-
Molecular Weight
291.32 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-11
Description
Hawkinsin is a cysteine derivative that is cysteine in which the thiol group is substituted by a [2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulfanediyl group. Hawkinsinuria is an inherited disorder which is characterized by the inability to break down the amino acid tyrosine. This results in the finding of certain metabolites in the urine, such as hawkinsin. It has a role as a biomarker and a human urinary metabolite. It is a dicarboxylic acid, a cysteine derivative, a cycloalkene, a diol, a tertiary allylic alcohol and a secondary allylic alcohol.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hawkinsin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-3-[2-(carboxymethyl)-2,5-dihydroxycyclohex-3-en-1-yl]sulfanylpropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H17NO6S/c12-7(10(16)17)5-19-8-3-6(13)1-2-11(8,18)4-9(14)15/h1-2,6-8,13,18H,3-5,12H2,(H,14,15)(H,16,17)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SPXVLTDISXZSFM-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1C(C=CC(C1SCC(C(=O)O)N)(CC(=O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H17NO6S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 DSSTox Substance ID

2.3.4 HMDB ID

2.3.5 Metabolomics Workbench ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.3.8 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (2-L-cystein-S-yl-1,4-dihydroxycyclohex-5-en-1- yl)acetic acid
  • hawkinsin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
291.32 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-3.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
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
291.07765844 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
291.07765844 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
166 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
387
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
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
4
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 Experimental Properties

3.2.1 Physical Description

Solid

5 Chemical Vendors

6 Food Additives and Ingredients

6.1 Associated Foods

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

Cytoplasm

8 Associated Disorders and Diseases

Disease
Hawkinsinuria
References

PubMed: 11978597, 10412819, 26226126

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Pathways

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 ChemIDplus

12.4 NORMAN Suspect List Exchange Classification

12.5 EPA DSSTox Classification

12.6 MolGenie Organic Chemistry Ontology

13 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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  5. ChEBI
  6. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. Metabolomics Workbench
  9. Wikidata
  10. Wikipedia
  11. PubChem
  12. 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
  13. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS