Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:18 UTC
Primary IDFDB012167
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). Gyromitrin has been detected, but not quantified in, mushrooms. This could make gyromitrin a potential biomarker for the consumption of these foods.
CAS Number16568-02-8
Structure
Thumb
Synonyms
SynonymSource
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
Acetaldehyde n-methyl-n-formylhydrazonebiospider
Acetaldehyde n-methylformylhydrazonebiospider
Acetaldehyde-n-formyl-n-methylhydrazonebiospider
Acetaldehyde-n-methyl-n-formylhydrazonebiospider
Acetaldehyde, n-formyl-n-methylhydrazonebiospider
Acetylaldehyde-n-methyl-n-formylhydrazonebiospider
Ethylidenemethylhydrazinecarboxaldehyde, 9CIdb_source
formic acid 2-ethylidene-1-methylhydrazidebiospider
Hydrazine carboxaldehyde, ethylidenemethyl-biospider
Hydrazine carboxyaldehyde, ethylidenemethyl-biospider
Hydrazinecarboxaldehyde, ethylidenemethyl-biospider
Hydrazinecarboxaldehyde, ethylidenemethyl- (9CI)biospider
N-methyl-n-formyl hydrazone of acetaldehydebiospider
N-methyl-n-formylhydrazone acetaldehydebiospider
N'-[-ethylidene]-n-methylformic hydrazidebiospider
N'-Ethylidene-N-formyl-N-methylhydrazinedb_source
N'-ethylidene-n-methylformic hydrazidebiospider
N'-ethylidene-n-methylformohydrazidebiospider
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
Chemical FormulaC4H8N2O
IUPAC nameN'-[(1Z)-ethylidene]-N-methylformohydrazide
InChI IdentifierInChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3-
InChI KeyIMAGWKUTFZRWSB-HYXAFXHYSA-N
Isomeric SMILESC\C=N/N(C)C=O
Average Molecular Weight100.1191
Monoisotopic Molecular Weight100.063662888
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 47.99%; H 8.05%; N 27.98%; O 15.98%DFC
Melting PointMp 19.5° (5°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGyromitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-9000000000-82bb9a93e2af8126e584Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-7900000000-0ede84e41f933f79197bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-48a51d43fac5c01ab28fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-9000000000-37521978a56f8b071a87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-62b339afc5956fa82611Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-0d2ea23b9aefd416147bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7b9c2846e3d7bb96feaaSpectrum
NMRNot Available
ChemSpider ID19957776
ChEMBL IDNot Available
KEGG Compound IDC08305
Pubchem Compound ID5365327
Pubchem Substance IDNot Available
ChEBI ID5583
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33952
CRC / DFC (Dictionary of Food Compounds) IDHDW49-S:HDW49-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001412
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGyromitrin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference