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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:43:34 UTC
Update Date2019-07-23 06:14:46 UTC
HMDB IDHMDB0033952
Secondary Accession Numbers
  • HMDB33952
Metabolite Identification
Common NameGyromitrin
DescriptionGyromitrin 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). Gyromitrin has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make gyromitrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Gyromitrin.
Structure
Data?1563862486
Synonyms
ValueSource
Acetaldehyde formylmethylhydrazoneHMDB
Acetaldehyde methylformylhydrazoneHMDB
Acetaldehyde N-formyl-N-methylhydrazoneHMDB
Acetaldehyde N-methyl-N-formylhydrazoneHMDB
Acetaldehyde N-methylformylhydrazoneHMDB
Acetaldehyde, N-formyl-N-methylhydrazoneHMDB
Acetaldehyde-N-formyl-N-methylhydrazoneHMDB
Acetaldehyde-N-methyl-N-formylhydrazoneHMDB
Acetylaldehyde-N-methyl-N-formylhydrazoneHMDB
Cetaldehyde methylformylhydrazoneHMDB
Ethylidene gyromitrinHMDB
Ethylidenemethyl-hydrazine carboxaldehydeHMDB
Ethylidenemethyl-hydrazine carboxyaldehydeHMDB
Ethylidenemethyl-hydrazinecarboxaldehydeHMDB
Ethylidenemethylhydrazinecarboxaldehyde, 9ciHMDB
Formic acid 2-ethylidene-1-methylhydrazideHMDB
Formic acid, 2-ethylidene-1-methylhydrazideHMDB
Formic acid, ethylidenemethylhydrazideHMDB
Hydrazinecarboxaldehyde, ethylidenemethyl- (9ci)HMDB
N'-ethylidene-N-formyl-N-methylhydrazineHMDB
N'-ethylidene-N-methylformic hydrazideHMDB
N'-ethylidene-N-methylformohydrazideHMDB
N'-[(1E)-ethylidene]-N-methylformic hydrazideHMDB
N'-[-ethylidene]-N-methylformic hydrazideHMDB
N-Methyl-N-formyl hydrazone OF acetaldehydeHMDB
N-Methyl-N-formylhydrazone acetaldehydeHMDB
Chemical FormulaC4H8N2O
Average Molecular Weight100.1191
Monoisotopic Molecular Weight100.063662888
IUPAC NameN'-[(1Z)-ethylidene]-N-methylformohydrazide
Traditional NameN'-[(1Z)-ethylidene]-N-methylformohydrazide
CAS Registry Number16568-02-8
SMILES
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 KeyIMAGWKUTFZRWSB-HYXAFXHYSA-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).
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassHydrazines and derivatives
Direct ParentN-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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Biological role:

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point19.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility36.2 g/LALOGPS
logP-0.61ALOGPS
logP-0.78ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)19.98ChemAxon
pKa (Strongest Basic)2.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.05 m³·mol⁻¹ChemAxon
Polarizability10.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-82bb9a93e2af8126e5842017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-7900000000-0ede84e41f933f79197b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-48a51d43fac5c01ab28f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-9000000000-37521978a56f8b071a872017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-62b339afc5956fa826112017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-0d2ea23b9aefd416147b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7b9c2846e3d7bb96feaa2017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012167
KNApSAcK IDC00001412
Chemspider ID19957776
KEGG Compound IDC08305
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGyromitrin
METLIN IDNot Available
PubChem Compound5365327
PDB IDNot Available
ChEBI ID5583
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .