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Hypoglycine A

PubChem CID
9081
Structure
Hypoglycine A_small.png
Hypoglycine A_3D_Structure.png
Molecular Formula
Synonyms
  • Hypoglycine
  • Hypoglycine A
  • 2-Methylenecyclopropanylalanine
  • Hypoglycin A
  • Cyclopropanealanine, 2-methylene-
Molecular Weight
141.17 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-27
Description
2-amino-3-(2-methylenecyclopropyl)propanoic acid is a non-proteinogenic alpha-amino acid that is alanine in which one of the methyl hydrogens has been replaced by a 2-methylenecyclopropyl group. The phytotoxin known as hypoglycin A is a mixture of the diastereoisomers that have L configuration at the amino-bearing carbon. It is a non-proteinogenic alpha-amino acid, a member of cyclopropanes and an olefinic compound.
Hypoglycine A has been reported in Dimocarpus longan, Nephelium ramboutan-ake, and Blighia sapida with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hypoglycine A.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-3-(2-methylidenecyclopropyl)propanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C=C1CC1CC(C(=O)O)N
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C7H11NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

156-56-9

2.3.2 ChEBI ID

2.3.3 DSSTox Substance ID

2.3.4 HMDB ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

2.3.7 NSC Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • hypoglycin
  • hypoglycin A
  • hypoglycin, (S)-isomer
  • hypoglycin, carboxy-(14)C-labeled

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
141.17 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
141.078978594 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
141.078978594 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
176
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
2
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

Yellow solid; [Merck Index]
Solid

3.2.2 Melting Point

280 - 284 °C

3.3 Chemical Classes

Biological Agents -> Plant Toxins

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

NIST Number
133007
Library
Main library
Total Peaks
85
m/z Top Peak
74
m/z 2nd Highest
96
m/z 3rd Highest
46
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

7.2 Biochemical Reactions

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Hypoglycemia-inducing component of the akee plant (Blighia sapida); [Merck Index] A water-soluble liver toxin found in the seeds, pods, and unripe fruit of the ackee plant; Ackee is the national fruit of Jamaica, where it is associated with Jamaican vomiting sickness or Toxic Hypoglycemic Syndrome (THS); [HSDB]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 Hazards Summary

Most poisonings occurred before 1955 in Jamaica or the West Indies; There were fatal cases in preschool children. Severe hypoglycemia below 29 mg/dl is followed by depletion of liver glycogen. Hepatitis may develop. [HSDB] Hypoglycin A & B are hypoglycemic agents from the unripe fruit of the akee plant; Hypoglycemia and vomiting precede the CNS symptoms of seizures and coma; [Ford, p. 919]
Ford - Ford MD, Delaney KA, Ling LJ, Erickson T (eds). Clinical Toxicology. Philadelphia: W.B. Saunders, 2001., p. 919

10 Toxicity

10.1 Toxicological Information

10.1.1 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 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

13 Interactions and Pathways

13.1 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 NORMAN Suspect List Exchange Classification

16.4 LOTUS Tree

16.5 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. ChEBI
    2-amino-3-(2-methylenecyclopropyl)propanoic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:136270
  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/
  3. DTP/NCI
    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
  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. EPA DSSTox
    3-(2-Methylidenecyclopropyl)alanine
    https://comptox.epa.gov/dashboard/DTXSID50871621
  6. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  7. 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
  8. Metabolomics Workbench
  9. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  10. Springer Nature
  11. Wikidata
  12. Wikipedia
  13. PubChem
  14. 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
  15. 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/
  16. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  17. PATENTSCOPE (WIPO)
CONTENTS