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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:36:16 UTC

Update Date

2021-09-26 22:58:33 UTC

HMDB ID

HMDB0248327

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aminooxyacetic acid

Description

Aminooxyacetic acid, also known as aminooxyacetate or AOA, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Based on a literature review a significant number of articles have been published on Aminooxyacetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Aminooxyacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Aminooxyacetic acid 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
(Carboxymethoxy)amine	ChEBI
(O-Carboxymethyl)hydroxylamine	ChEBI
2-(Aminooxy)acetic acid	ChEBI
2-Aminooxyethanoic acid	ChEBI
AOA	ChEBI
AOAA	ChEBI
Carboxymethoxyamine	ChEBI
U-7524	ChEBI
2-(Aminooxy)acetate	Generator
2-Aminooxyethanoate	Generator
Aminooxyacetate	Generator
Acid, aminooxyacetic	HMDB
Aminooxy-acetic acid	HMDB
Aminooxy-acetate	HMDB

Chemical Formula

C₂H₅NO₃

Average Molecular Weight

91.066

Monoisotopic Molecular Weight

91.026943031

IUPAC Name

2-(aminooxy)acetic acid

Traditional Name

(aminooxy)acetic acid

CAS Registry Number

Not Available

SMILES

NOCC(O)=O

InChI Identifier

InChI=1S/C2H5NO3/c3-6-1-2(4)5/h1,3H2,(H,4,5)

InChI Key

NQRKYASMKDDGHT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen 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

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	-0.79	ALOGPS
logP	-2.2	ChemAxon
logS	0.76	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	4.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	18.42 m³·mol⁻¹	ChemAxon
Polarizability	7.61 Å³	ChemAxon
Number of Rings	0	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]+	131.725	30932474
DeepCCS	[M-H]-	128.935	30932474
DeepCCS	[M-2H]-	165.524	30932474
DeepCCS	[M+Na]+	139.958	30932474
AllCCS	[M+H]+	124.6	32859911
AllCCS	[M+H-H2O]+	120.3	32859911
AllCCS	[M+NH4]+	128.7	32859911
AllCCS	[M+Na]+	129.9	32859911
AllCCS	[M-H]-	122.5	32859911
AllCCS	[M+Na-2H]-	127.2	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aminooxyacetic acid	NOCC(O)=O	1793.9	Standard polar	33892256
Aminooxyacetic acid	NOCC(O)=O	1061.9	Standard non polar	33892256
Aminooxyacetic acid	NOCC(O)=O	1034.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aminooxyacetic acid,2TMS,isomer #1	C[Si](C)(C)NOCC(=O)O[Si](C)(C)C	1183.6	Semi standard non polar	33892256
Aminooxyacetic acid,2TMS,isomer #1	C[Si](C)(C)NOCC(=O)O[Si](C)(C)C	1246.6	Standard non polar	33892256
Aminooxyacetic acid,2TMS,isomer #1	C[Si](C)(C)NOCC(=O)O[Si](C)(C)C	1369.1	Standard polar	33892256
Aminooxyacetic acid,2TMS,isomer #2	C[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C	1365.4	Semi standard non polar	33892256
Aminooxyacetic acid,2TMS,isomer #2	C[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C	1290.9	Standard non polar	33892256
Aminooxyacetic acid,2TMS,isomer #2	C[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C	1577.4	Standard polar	33892256
Aminooxyacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CON([Si](C)(C)C)[Si](C)(C)C	1396.0	Semi standard non polar	33892256
Aminooxyacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CON([Si](C)(C)C)[Si](C)(C)C	1337.0	Standard non polar	33892256
Aminooxyacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CON([Si](C)(C)C)[Si](C)(C)C	1372.3	Standard polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NOCC(=O)O[Si](C)(C)C(C)(C)C	1599.0	Semi standard non polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NOCC(=O)O[Si](C)(C)C(C)(C)C	1608.6	Standard non polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NOCC(=O)O[Si](C)(C)C(C)(C)C	1632.4	Standard polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C(C)(C)C	1780.0	Semi standard non polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C(C)(C)C	1665.2	Standard non polar	33892256
Aminooxyacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(OCC(=O)O)[Si](C)(C)C(C)(C)C	1714.0	Standard polar	33892256
Aminooxyacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CON([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2026.7	Semi standard non polar	33892256
Aminooxyacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CON([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1951.2	Standard non polar	33892256
Aminooxyacetic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CON([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1763.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Aminooxyacetic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-3c1e974a82b7aa1974ee	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9000000000-33664d6bdf800839259a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aminooxyacetic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Aminooxyacetic acid 10V, Positive-QTOF	splash10-0006-9000000000-e2215398edd7d786d861	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 20V, Positive-QTOF	splash10-0006-9000000000-0b013b004cea323bd602	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 40V, Positive-QTOF	splash10-0006-9000000000-bb5495444c437534fc39	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 10V, Negative-QTOF	splash10-0006-9000000000-894a9edea4a3413dfdcb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 20V, Negative-QTOF	splash10-0006-9000000000-ea3d01c2a99ab7b549c0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 40V, Negative-QTOF	splash10-0092-9000000000-5110cf44cd4b3d433ff3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 10V, Positive-QTOF	splash10-0006-9000000000-fd6fe6f28e3add62100e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 20V, Positive-QTOF	splash10-0002-9000000000-997e13c8d0b81ee414c6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 40V, Positive-QTOF	splash10-0007-9000000000-5cb0e1e9a753a30f2f44	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 10V, Negative-QTOF	splash10-0006-9000000000-a52575b6924a2b9ee3f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 20V, Negative-QTOF	splash10-006x-9000000000-56e479bb23b2aac0890a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aminooxyacetic acid 40V, Negative-QTOF	splash10-00dl-9000000000-1a0e83e647c833e6bfce	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	¹³C NMR Spectrum (1D, 200 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	¹H NMR Spectrum (1D, 300 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	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	¹H NMR Spectrum (1D, 600 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, 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

DB02079

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

280

KEGG Compound ID

Not Available

BioCyc ID

CARBOXYMETHOXYLAMINE

BiGG ID

Not Available

Wikipedia Link

Aminooxyacetic_acid

METLIN ID

Not Available

PubChem Compound

286

PDB ID

Not Available

ChEBI ID

40823

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 Aminooxyacetic acid (HMDB0248327)

MOL for HMDB0248327 (Aminooxyacetic acid)

3D MOL for HMDB0248327 (Aminooxyacetic acid)

3D SDF for HMDB0248327 (Aminooxyacetic acid)

3D-SDF for HMDB0248327 (Aminooxyacetic acid)

PDB for HMDB0248327 (Aminooxyacetic acid)

3D PDB for HMDB0248327 (Aminooxyacetic acid)

SMILES for HMDB0248327 (Aminooxyacetic acid)

INCHI for HMDB0248327 (Aminooxyacetic acid)

Structure for HMDB0248327 (Aminooxyacetic acid)

3D Structure for HMDB0248327 (Aminooxyacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra