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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:43:34 UTC

Update Date

2023-02-21 17:23:48 UTC

HMDB ID

HMDB0033952

Secondary Accession Numbers

HMDB33952

Metabolite Identification

Common Name

Gyromitrin

Description

Gyromitrin 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetaldehyde formylmethylhydrazone	HMDB
Acetaldehyde methylformylhydrazone	HMDB
Acetaldehyde N-formyl-N-methylhydrazone	HMDB
Acetaldehyde N-methyl-N-formylhydrazone	HMDB
Acetaldehyde N-methylformylhydrazone	HMDB
Acetaldehyde, N-formyl-N-methylhydrazone	HMDB
Acetaldehyde-N-formyl-N-methylhydrazone	HMDB
Acetaldehyde-N-methyl-N-formylhydrazone	HMDB
Acetylaldehyde-N-methyl-N-formylhydrazone	HMDB
Cetaldehyde methylformylhydrazone	HMDB
Ethylidene gyromitrin	HMDB
Ethylidenemethyl-hydrazine carboxaldehyde	HMDB
Ethylidenemethyl-hydrazine carboxyaldehyde	HMDB
Ethylidenemethyl-hydrazinecarboxaldehyde	HMDB
Ethylidenemethylhydrazinecarboxaldehyde, 9ci	HMDB
Formic acid 2-ethylidene-1-methylhydrazide	HMDB
Formic acid, 2-ethylidene-1-methylhydrazide	HMDB
Formic acid, ethylidenemethylhydrazide	HMDB
Hydrazinecarboxaldehyde, ethylidenemethyl- (9ci)	HMDB
N'-ethylidene-N-formyl-N-methylhydrazine	HMDB
N'-ethylidene-N-methylformic hydrazide	HMDB
N'-ethylidene-N-methylformohydrazide	HMDB
N'-[(1E)-ethylidene]-N-methylformic hydrazide	HMDB
N'-[-ethylidene]-N-methylformic hydrazide	HMDB
N-Methyl-N-formyl hydrazone OF acetaldehyde	HMDB
N-Methyl-N-formylhydrazone acetaldehyde	HMDB

Chemical Formula

C₄H₈N₂O

Average Molecular Weight

100.1191

Monoisotopic Molecular Weight

100.063662888

IUPAC Name

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

Traditional Name

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

CAS Registry Number

16568-02-8

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 Key

IMAGWKUTFZRWSB-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).

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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033952)
Cytoplasm (HMDB: HMDB0033952)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033952)

Source

Exogenous

Food

Food (HMDB: HMDB0033952)

Plant (HMDB: HMDB0033952)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033952)

Environmental role

Environmental contaminant (HMDB: HMDB0033952)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	19.5 °C	Not Available
Boiling Point	135.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	360800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.300 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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 Acidic)	19.98	ChemAxon
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	10.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	124.706	30932474
DeepCCS	[M-H]-	122.699	30932474
DeepCCS	[M-2H]-	158.601	30932474
DeepCCS	[M+Na]+	133.212	30932474
AllCCS	[M+H]+	126.5	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	130.5	32859911
AllCCS	[M+Na]+	131.6	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	129.2	32859911
AllCCS	[M+HCOO]-	133.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gyromitrin	C\C=N/N(C)C=O	1326.7	Standard polar	33892256
Gyromitrin	C\C=N/N(C)C=O	848.0	Standard non polar	33892256
Gyromitrin	C\C=N/N(C)C=O	969.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gyromitrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-82bb9a93e2af8126e584	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gyromitrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 10V, Positive-QTOF	splash10-0uk9-7900000000-0ede84e41f933f79197b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 20V, Positive-QTOF	splash10-00di-9000000000-48a51d43fac5c01ab28f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 40V, Positive-QTOF	splash10-05dl-9000000000-37521978a56f8b071a87	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 10V, Negative-QTOF	splash10-00di-9000000000-62b339afc5956fa82611	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 20V, Negative-QTOF	splash10-00di-9000000000-0d2ea23b9aefd416147b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 40V, Negative-QTOF	splash10-0006-9000000000-7b9c2846e3d7bb96feaa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 10V, Positive-QTOF	splash10-0fk9-9500000000-97902feb14fdd58896a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 20V, Positive-QTOF	splash10-00di-9000000000-4ad1cb2a85d84cb9a8df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 40V, Positive-QTOF	splash10-0002-9000000000-cd336bdaba13a492b8ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 10V, Negative-QTOF	splash10-052f-9000000000-7275df4cc5eb82427f08	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 20V, Negative-QTOF	splash10-0006-9000000000-e4aad895b9211f0b93a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gyromitrin 40V, Negative-QTOF	splash10-0006-9000000000-77abacf2e152c7efca1b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gyromitrin

METLIN ID

Not Available

PubChem Compound

5365327

PDB ID

Not Available

ChEBI ID

5583

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1379341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Gyromitrin (HMDB0033952)

MOL for HMDB0033952 (Gyromitrin)

3D MOL for HMDB0033952 (Gyromitrin)

3D SDF for HMDB0033952 (Gyromitrin)

3D-SDF for HMDB0033952 (Gyromitrin)

PDB for HMDB0033952 (Gyromitrin)

3D PDB for HMDB0033952 (Gyromitrin)

SMILES for HMDB0033952 (Gyromitrin)

INCHI for HMDB0033952 (Gyromitrin)

Structure for HMDB0033952 (Gyromitrin)

3D Structure for HMDB0033952 (Gyromitrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra