ContaminantDB: Gyromitrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-07-03 20:54:23 UTC

Update Date

2016-11-09 01:08:40 UTC

Accession Number

CHEM002042

Identification

Common Name

Gyromitrin

Class

Small Molecule

Description

Gyromitrin is found in mushrooms. Toxin from the fungus Gyromitra esculenta. Freq. cause of mushroom poisoning Gyromitrin is a toxin and possible carcinogen present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Food Toxin
Fungal Toxin
Hydrazine
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Acetaldehyde methylformylhydrazone	Kegg
N-Methyl-N-formylhydrazone acetaldehyde	MeSH
Ethylidene gyromitrin	MeSH

Chemical Formula

C₄H₈N₂O

Average Molecular Mass

100.119 g/mol

Monoisotopic Mass

100.064 g/mol

CAS Registry Number

16568-02-8

IUPAC Name

N'-[(1E)-ethylidene]-N-methylformohydrazide

Traditional Name

ethylidene gyromitrin

SMILES

[H]\C(C)=N/N(C)C=O

InChI Identifier

InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3+

InChI Key

IMAGWKUTFZRWSB-HWKANZROSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-alkylated hydrazones. These are organonitrogen compounds containing a hydrazone group that is substituted with an alkyl group. They have the generic structure RNN=C(R')R\" (R= alkyl group; R',R\"= H or organyl group).

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Hydrazines and derivatives

Direct Parent

N-alkylated hydrazones

Alternative Parents

Substituents

N-alkylated hydrazone
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Mushroom toxins (C08305 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	19.5°C
Boiling Point	143 °C, 416°K, 289 °F
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	36.2 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.78	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Basic)	2.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.05 m³·mol⁻¹	ChemAxon
Polarizability	10.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-6886f52c8308abf01476	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-9400000000-1512ed65eadbc59fb19f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054o-9000000000-4c4b3367f2af862207db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-31d6770e020842c1618b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0595-9000000000-e013bb93be9ce728ea13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4f0872f655ea8b457844	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

The toxicity is caused by the conversion of the hydrazine (gyromitrin) to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when gyromitrin begins to be metabolized and it undergoes hydrolysis. The necrosis and steatosis are caused by monomethylhydrazine. (3)

Metabolism

Gyromitrin is converted to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when gyromitrin begins to be metabolized and it undergoes hydrolysis. (3)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (2)

Uses/Sources

Gyromitrin is a toxic and possibly carcinogenic chemical present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta. (3)

Minimum Risk Level

Not Available

Health Effects

Consuming large amounts of gyromitrin, such as are found in untreated false morels, may lead to catastrophic liver failure and death. (3)

Symptoms

Initial symptoms of gyromitrin exposure include headache, nausea and dizziness. As gyromitrin is quite volatile, even just the presence of false morels in a poorly ventilated space may be enough to cause these symptoms. (3)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001412

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Gyromitrin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

9548611

Kegg Compound ID

C08305

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Gyromitrin (CHEM002042)

Structure for CHEM002042: Gyromitrin