You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
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 is a moderately basic compound (based on its pKa). Outside of the human body, Gyromitrin has been detected, but not quantified in, mushrooms. This could make gyromitrin a potential biomarker for the consumption of these foods.
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 Properties
PropertyValueReference
Melting Point19.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-82bb9a93e2af8126e584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-7900000000-0ede84e41f933f79197bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-48a51d43fac5c01ab28fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-9000000000-37521978a56f8b071a87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-62b339afc5956fa82611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-0d2ea23b9aefd416147bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7b9c2846e3d7bb96feaaSpectrum
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 ID
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.. .