Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:52:35 UTC

Update Date

2021-09-26 23:03:32 UTC

HMDB ID

HMDB0251514

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Aminoisoxazolidin-3-one

Description

4-amino-1,2-oxazolidin-3-one, also known as cycloserine, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 4-amino-1,2-oxazolidin-3-one is a very strong basic compound (based on its pKa). 4-amino-1,2-oxazolidin-3-one is a potentially toxic compound. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-aminoisoxazolidin-3-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Aminoisoxazolidin-3-one 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
Cycloserine	ChEBI

Chemical Formula

C₃H₆N₂O₂

Average Molecular Weight

102.0919

Monoisotopic Molecular Weight

102.042927446

IUPAC Name

4-amino-1,2-oxazolidin-3-one

Traditional Name

(+-)-4-amino-3-isoxazolidinone

CAS Registry Number

Not Available

SMILES

NC1CONC1=O

InChI Identifier

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)

InChI Key

DYDCUQKUCUHJBH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Oxazolidinone
Isoxazolidine
Organoheterocyclic compound
Azacycle
Oxacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

primary amino compound (CHEBI:23503 )
serine derivative (CHEBI:23503 )
oxazolidines (CHEBI:23503 )
hydroxamic acid ester (CHEBI:23503 )
Amino acid derivatives (C06682 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	-2.3	ALOGPS
logP	-2.4	ChemAxon
logS	0.93	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	8.93 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]+	129.93	30932474
DeepCCS	[M-H]-	127.133	30932474
DeepCCS	[M-2H]-	163.516	30932474
DeepCCS	[M+Na]+	138.117	30932474
AllCCS	[M+H]+	122.3	32859911
AllCCS	[M+H-H2O]+	117.3	32859911
AllCCS	[M+NH4]+	126.9	32859911
AllCCS	[M+Na]+	128.3	32859911
AllCCS	[M-H]-	114.2	32859911
AllCCS	[M+Na-2H]-	117.3	32859911
AllCCS	[M+HCOO]-	120.8	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Aminoisoxazolidin-3-one,1TMS,isomer #1	C[Si](C)(C)NC1CONC1=O	1409.2	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TMS,isomer #1	C[Si](C)(C)NC1CONC1=O	1291.9	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TMS,isomer #1	C[Si](C)(C)NC1CONC1=O	2768.3	Standard polar	33892256
4-Aminoisoxazolidin-3-one,1TMS,isomer #2	C[Si](C)(C)N1OCC(N)C1=O	1323.3	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TMS,isomer #2	C[Si](C)(C)N1OCC(N)C1=O	1160.5	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TMS,isomer #2	C[Si](C)(C)N1OCC(N)C1=O	2431.3	Standard polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #1	C[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C	1531.1	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #1	C[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C	1513.4	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #1	C[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C	2518.8	Standard polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #2	C[Si](C)(C)NC1CON([Si](C)(C)C)C1=O	1456.0	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #2	C[Si](C)(C)NC1CON([Si](C)(C)C)C1=O	1400.6	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TMS,isomer #2	C[Si](C)(C)NC1CON([Si](C)(C)C)C1=O	1977.5	Standard polar	33892256
4-Aminoisoxazolidin-3-one,3TMS,isomer #1	C[Si](C)(C)N1OCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1605.1	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,3TMS,isomer #1	C[Si](C)(C)N1OCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1569.0	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,3TMS,isomer #1	C[Si](C)(C)N1OCC(N([Si](C)(C)C)[Si](C)(C)C)C1=O	1668.6	Standard polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CONC1=O	1607.8	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CONC1=O	1554.4	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1CONC1=O	2765.7	Standard polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1OCC(N)C1=O	1516.4	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1OCC(N)C1=O	1414.9	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1OCC(N)C1=O	2456.4	Standard polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C(C)(C)C	1896.2	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C(C)(C)C	1956.6	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1CONC1=O)[Si](C)(C)C(C)(C)C	2389.5	Standard polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CON([Si](C)(C)C(C)(C)C)C1=O	1873.7	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CON([Si](C)(C)C(C)(C)C)C1=O	1851.3	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1CON([Si](C)(C)C(C)(C)C)C1=O	1994.7	Standard polar	33892256
4-Aminoisoxazolidin-3-one,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	2151.2	Semi standard non polar	33892256
4-Aminoisoxazolidin-3-one,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	2225.4	Standard non polar	33892256
4-Aminoisoxazolidin-3-one,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1OCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=O	1977.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoisoxazolidin-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0e7a5a8b0f7ce48e4509	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoisoxazolidin-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Aminoisoxazolidin-3-one 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 - 4-Aminoisoxazolidin-3-one 10V, Positive-QTOF	splash10-0udi-3900000000-9d87a38dceea150c7066	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 20V, Positive-QTOF	splash10-0f7c-9300000000-ec8bd6d69b2d6749ce74	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 40V, Positive-QTOF	splash10-0596-9000000000-4c4033f992b36b67d2a9	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 10V, Negative-QTOF	splash10-0udi-3900000000-216e3c23030c76788391	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 20V, Negative-QTOF	splash10-0k96-9300000000-53c55a634f4e5e2c9b9c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 40V, Negative-QTOF	splash10-052f-9000000000-ac299a9dab12f2841e38	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 10V, Positive-QTOF	splash10-0udi-2900000000-af5f60a17593742507ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 20V, Positive-QTOF	splash10-0udi-9500000000-d924d3621a2997cacca8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 40V, Positive-QTOF	splash10-0006-9000000000-cef77fb45fbfe2314d83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 10V, Negative-QTOF	splash10-0udl-8900000000-7a8c1bbde4ca23e0be68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 20V, Negative-QTOF	splash10-0006-9100000000-f54362d50602abb52b39	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Aminoisoxazolidin-3-one 40V, Negative-QTOF	splash10-0006-9000000000-f3902365bdb4a7cf3b71	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H 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	¹³C NMR Spectrum (1D, 400 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	¹H NMR Spectrum (1D, 500 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	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	¹H NMR Spectrum (1D, 700 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	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

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06682

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

401

PDB ID

Not Available

ChEBI ID

23503

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 4-Aminoisoxazolidin-3-one (HMDB0251514)

MOL for HMDB0251514 (4-Aminoisoxazolidin-3-one)

3D MOL for HMDB0251514 (4-Aminoisoxazolidin-3-one)

3D SDF for HMDB0251514 (4-Aminoisoxazolidin-3-one)

3D-SDF for HMDB0251514 (4-Aminoisoxazolidin-3-one)

PDB for HMDB0251514 (4-Aminoisoxazolidin-3-one)

3D PDB for HMDB0251514 (4-Aminoisoxazolidin-3-one)

SMILES for HMDB0251514 (4-Aminoisoxazolidin-3-one)

INCHI for HMDB0251514 (4-Aminoisoxazolidin-3-one)

Structure for HMDB0251514 (4-Aminoisoxazolidin-3-one)

3D Structure for HMDB0251514 (4-Aminoisoxazolidin-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra