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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:27:29 UTC

Update Date

2021-09-26 23:09:24 UTC

HMDB ID

HMDB0254955

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Muscimol

Description

Muscimol belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Muscimol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Muscimol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Muscimol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Muscimol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(Aminomethyl)-3(2H)-isoxazolone	ChEBI
Agarin	MeSH
Pantherine	MeSH

Chemical Formula

C₄H₆N₂O₂

Average Molecular Weight

114.1026

Monoisotopic Molecular Weight

114.042927446

IUPAC Name

5-(aminomethyl)-1,2-oxazol-3-ol

Traditional Name

muscimol

CAS Registry Number

Not Available

SMILES

NCC1=CC(O)=NO1

InChI Identifier

InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)

InChI Key

ZJQHPWUVQPJPQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Azole
Isoxazole
Heteroaromatic compound
Lactam
Organoheterocyclic compound
Oxacycle
Azacycle
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

alkaloid (CHEBI:7035 )
primary amino compound (CHEBI:7035 )
isoxazoles (CHEBI:7035 )
Alkaloids (C08311 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0254955)
Extracellular (HMDB: HMDB0254955)

Source

Exogenous

Exogenous (HMDB: HMDB0254955)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Psychotropic drug (HMDB: HMDB0254955)

GABA agonist (HMDB: HMDB0254955)

Biological role

Fungal metabolite (HMDB: HMDB0254955)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.95	ALOGPS
logP	-1.4	ChemAxon
logS	-0.29	ALOGPS
pKa (Strongest Acidic)	5.78	ChemAxon
pKa (Strongest Basic)	7.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.15 m³·mol⁻¹	ChemAxon
Polarizability	10.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	125.029	30932474
DeepCCS	[M-H]-	123.134	30932474
DeepCCS	[M-2H]-	158.896	30932474
DeepCCS	[M+Na]+	133.414	30932474
AllCCS	[M+H]+	124.5	32859911
AllCCS	[M+H-H2O]+	119.6	32859911
AllCCS	[M+NH4]+	129.0	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	120.6	32859911
AllCCS	[M+Na-2H]-	123.1	32859911
AllCCS	[M+HCOO]-	125.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Muscimol	NCC1=CC(O)=NO1	1966.0	Standard polar	33892256
Muscimol	NCC1=CC(O)=NO1	1324.1	Standard non polar	33892256
Muscimol	NCC1=CC(O)=NO1	1186.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Muscimol,2TMS,isomer #1	C[Si](C)(C)NCC1=CC(O[Si](C)(C)C)=NO1	1438.3	Semi standard non polar	33892256
Muscimol,2TMS,isomer #1	C[Si](C)(C)NCC1=CC(O[Si](C)(C)C)=NO1	1493.4	Standard non polar	33892256
Muscimol,2TMS,isomer #1	C[Si](C)(C)NCC1=CC(O[Si](C)(C)C)=NO1	1745.2	Standard polar	33892256
Muscimol,2TMS,isomer #2	C[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C	1691.6	Semi standard non polar	33892256
Muscimol,2TMS,isomer #2	C[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C	1649.6	Standard non polar	33892256
Muscimol,2TMS,isomer #2	C[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C	1934.7	Standard polar	33892256
Muscimol,3TMS,isomer #1	C[Si](C)(C)OC1=NOC(CN([Si](C)(C)C)[Si](C)(C)C)=C1	1630.2	Semi standard non polar	33892256
Muscimol,3TMS,isomer #1	C[Si](C)(C)OC1=NOC(CN([Si](C)(C)C)[Si](C)(C)C)=C1	1637.6	Standard non polar	33892256
Muscimol,3TMS,isomer #1	C[Si](C)(C)OC1=NOC(CN([Si](C)(C)C)[Si](C)(C)C)=C1	1693.9	Standard polar	33892256
Muscimol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=CC(O[Si](C)(C)C(C)(C)C)=NO1	1894.4	Semi standard non polar	33892256
Muscimol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=CC(O[Si](C)(C)C(C)(C)C)=NO1	1948.8	Standard non polar	33892256
Muscimol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=CC(O[Si](C)(C)C(C)(C)C)=NO1	1964.1	Standard polar	33892256
Muscimol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2104.0	Semi standard non polar	33892256
Muscimol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2104.7	Standard non polar	33892256
Muscimol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC1=CC(O)=NO1)[Si](C)(C)C(C)(C)C	2057.0	Standard polar	33892256
Muscimol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NOC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2251.8	Semi standard non polar	33892256
Muscimol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NOC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2279.3	Standard non polar	33892256
Muscimol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NOC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2051.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Muscimol EI-B (Non-derivatized)	splash10-003r-9000000000-8a5c7c8119385828f867	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9200000000-9b83d1483d2e2c7ddeb6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Muscimol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Muscimol LC-ESI-QQ , positive-QTOF	splash10-014i-3900000000-68483046cfeb7ca5d01b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Muscimol LC-ESI-QQ , positive-QTOF	splash10-0002-9000000000-6de63da45a13d454cce3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Muscimol LC-ESI-QQ , positive-QTOF	splash10-00kb-9000000000-6b5110dcd6fa6b4422e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Muscimol LC-ESI-QQ , positive-QTOF	splash10-014i-9000000000-c2fbac7befc44bdfbe43	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Muscimol LC-ESI-QQ , positive-QTOF	splash10-014r-9000000000-f4eda66dfcf7c0a3918c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 10V, Positive-QTOF	splash10-014i-3900000000-b58c956f64f0f049a64c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 20V, Positive-QTOF	splash10-014j-9600000000-164169f85b3f6f6c94db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 40V, Positive-QTOF	splash10-100u-9000000000-04ba67371609e08956ee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 10V, Negative-QTOF	splash10-03di-3900000000-2b5bf5ca3739d495ccc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 20V, Negative-QTOF	splash10-03di-9800000000-ac88ce1ff672c846f8b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 40V, Negative-QTOF	splash10-0006-9000000000-2bbb93920e5a57deff3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 10V, Positive-QTOF	splash10-00kb-9400000000-f76809dd9d9cfaa33245	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 20V, Positive-QTOF	splash10-0002-9100000000-6f3f42f82def807255c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 40V, Positive-QTOF	splash10-000i-9000000000-aa53a456f47c4c6734b8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 10V, Negative-QTOF	splash10-01ot-9500000000-e072f5ae3316e619c7f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 20V, Negative-QTOF	splash10-0006-9000000000-4072272fb0cceffda304	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Muscimol 40V, Negative-QTOF	splash10-0f6x-9000000000-79bfba881e929cb7e2c1	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12458

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001423

Chemspider ID

4116

KEGG Compound ID

C08311

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Muscimol

METLIN ID

Not Available

PubChem Compound

4266

PDB ID

Not Available

ChEBI ID

7035

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Muscimol (HMDB0254955)

MOL for HMDB0254955 (Muscimol)

3D MOL for HMDB0254955 (Muscimol)

3D SDF for HMDB0254955 (Muscimol)

3D-SDF for HMDB0254955 (Muscimol)

PDB for HMDB0254955 (Muscimol)

3D PDB for HMDB0254955 (Muscimol)

SMILES for HMDB0254955 (Muscimol)

INCHI for HMDB0254955 (Muscimol)

Structure for HMDB0254955 (Muscimol)

3D Structure for HMDB0254955 (Muscimol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra