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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:29:40 UTC

Update Date

2022-09-22 17:45:02 UTC

HMDB ID

HMDB0252570

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gaboxadol

Description

Gaboxadol, also known as THIP, 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. In 2015, Lundbeck sold its rights to the molecule to Ovid Therapeutics, whose plan is to develop it for FXS and Angelman syndrome. Gaboxadol is a very strong basic compound (based on its pKa). It was not until 1996 that researchers attempted to harness gaboxadol's frequently reported sedative "adverse effect" for the treatment of insomnia, resulting in a series of clinical trials sponsored by Lundbeck and Merck. Lundbeck states that gaboxadol also increases deep sleep (stage 4). It acts on the GABA system, but in a different way from benzodiazepines, Z-Drugs, and barbiturates. It is, however, not reinforcing like benzodiazepines are. It is known internally in Ovid as OV101. In March, 2007, Merck and Lundbeck cancelled work on the drug, citing safety concerns and the failure of an efficacy trial. In the early 1980s gaboxadol was the subject of a series of pilot studies that tested its efficacy as an analgesic and anxiolytic, as well as a treatment for tardive dyskinesia, Huntington's disease, Alzheimer's disease, and spasticity. This compound has been identified in human blood as reported by (PMID: 31557052 ). Gaboxadol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Gaboxadol 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
THIP	Kegg
4,5,6,7-tetrahydroisoxazolo(5,4-c)Pyridin-3-ol	MeSH

Chemical Formula

C₆H₈N₂O₂

Average Molecular Weight

140.1399

Monoisotopic Molecular Weight

140.05857751

IUPAC Name

2H,3H,4H,5H,6H,7H-[1,2]oxazolo[5,4-c]pyridin-3-one

Traditional Name

gaboxadol

CAS Registry Number

Not Available

SMILES

O=C1NOC2=C1CCNC2

InChI Identifier

InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)

InChI Key

ZXRVKCBLGJOCEE-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
Heteroaromatic compound
Isoxazole
Azole
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxazole (CHEBI:34373 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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	-1.3	ALOGPS
logP	-2	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	5.12	ChemAxon
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.5 m³·mol⁻¹	ChemAxon
Polarizability	13.31 Å³	ChemAxon
Number of Rings	2	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]+	127.096	30932474
DeepCCS	[M-H]-	124.784	30932474
DeepCCS	[M-2H]-	160.76	30932474
DeepCCS	[M+Na]+	135.651	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	123.6	32859911
AllCCS	[M+NH4]+	132.9	32859911
AllCCS	[M+Na]+	134.2	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	127.9	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gaboxadol	O=C1NOC2=C1CCNC2	2309.9	Standard polar	33892256
Gaboxadol	O=C1NOC2=C1CCNC2	1352.9	Standard non polar	33892256
Gaboxadol	O=C1NOC2=C1CCNC2	1625.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gaboxadol,1TMS,isomer #1	C[Si](C)(C)N1OC2=C(CCNC2)C1=O	1585.5	Semi standard non polar	33892256
Gaboxadol,1TMS,isomer #1	C[Si](C)(C)N1OC2=C(CCNC2)C1=O	1560.9	Standard non polar	33892256
Gaboxadol,1TMS,isomer #1	C[Si](C)(C)N1OC2=C(CCNC2)C1=O	2266.1	Standard polar	33892256
Gaboxadol,1TMS,isomer #2	C[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	1646.4	Semi standard non polar	33892256
Gaboxadol,1TMS,isomer #2	C[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	1726.5	Standard non polar	33892256
Gaboxadol,1TMS,isomer #2	C[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	2342.0	Standard polar	33892256
Gaboxadol,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C)C2=O	1707.6	Semi standard non polar	33892256
Gaboxadol,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C)C2=O	1791.4	Standard non polar	33892256
Gaboxadol,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C)C2=O	2065.8	Standard polar	33892256
Gaboxadol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OC2=C(CCNC2)C1=O	1847.2	Semi standard non polar	33892256
Gaboxadol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OC2=C(CCNC2)C1=O	1792.4	Standard non polar	33892256
Gaboxadol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OC2=C(CCNC2)C1=O	2374.1	Standard polar	33892256
Gaboxadol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	1939.4	Semi standard non polar	33892256
Gaboxadol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	2003.9	Standard non polar	33892256
Gaboxadol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)O[NH]C2=O	2587.1	Standard polar	33892256
Gaboxadol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C(C)(C)C)C2=O	2189.9	Semi standard non polar	33892256
Gaboxadol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C(C)(C)C)C2=O	2265.5	Standard non polar	33892256
Gaboxadol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)ON([Si](C)(C)C(C)(C)C)C2=O	2275.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gaboxadol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pp-7900000000-3f464c21f7a2942a54a2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gaboxadol 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 - Gaboxadol 10V, Positive-QTOF	splash10-0006-0900000000-99ae65689d4c5172f4ac	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 20V, Positive-QTOF	splash10-0006-1900000000-83d2598351298d95b4d7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 40V, Positive-QTOF	splash10-001i-9100000000-9679022b9f2e092edd7e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 10V, Negative-QTOF	splash10-000i-0900000000-e3a549beadb364d499b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 20V, Negative-QTOF	splash10-000i-1900000000-2c0e46c4dc3a7e76b266	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 40V, Negative-QTOF	splash10-0006-9000000000-afeb636cbed74297f642	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 10V, Positive-QTOF	splash10-0006-0900000000-f0e0a5eee91f78e12b7a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 20V, Positive-QTOF	splash10-0006-3900000000-06bac57a16b6d95de481	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 40V, Positive-QTOF	splash10-001l-9100000000-9b2eb6996eee5a559786	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 10V, Negative-QTOF	splash10-000i-3900000000-7805ae1b442d50a8759c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 20V, Negative-QTOF	splash10-000i-7900000000-485c24fd4fcf5a761d38	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gaboxadol 40V, Negative-QTOF	splash10-0006-9000000000-e033059c865e77d713e0	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06554

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C13693

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gaboxadol

METLIN ID

Not Available

PubChem Compound

3448

PDB ID

Not Available

ChEBI ID

Not Available

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 Gaboxadol (HMDB0252570)

MOL for HMDB0252570 (Gaboxadol)

3D MOL for HMDB0252570 (Gaboxadol)

3D SDF for HMDB0252570 (Gaboxadol)

3D-SDF for HMDB0252570 (Gaboxadol)

PDB for HMDB0252570 (Gaboxadol)

3D PDB for HMDB0252570 (Gaboxadol)

SMILES for HMDB0252570 (Gaboxadol)

INCHI for HMDB0252570 (Gaboxadol)

Structure for HMDB0252570 (Gaboxadol)

3D Structure for HMDB0252570 (Gaboxadol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra