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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:16:40 UTC

Update Date

2021-09-26 23:04:56 UTC

HMDB ID

HMDB0252391

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Fluoro-2-oxopropanoic acid

Description

3-Fluoro-2-oxopropanoic acid, also known as 3-fluoropyruvate or fluoropyruvic acid, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Based on a literature review a significant number of articles have been published on 3-Fluoro-2-oxopropanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-fluoro-2-oxopropanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Fluoro-2-oxopropanoic 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
3-Fluoropyruvate	ChEBI
Fluoropyruvic acid	ChEBI
3-Fluoropyruvic acid	Generator
Fluoropyruvate	Generator
3-Fluoro-2-oxopropanoate	Generator
3-Fluoropyruvate, sodium salt	HMDB
3-Fluoro-2-oxopropanoic acid	ChEBI

Chemical Formula

C₃H₃FO₃

Average Molecular Weight

106.052

Monoisotopic Molecular Weight

106.00662212

IUPAC Name

3-fluoro-2-oxopropanoic acid

Traditional Name

fluoropyruvic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(=O)CF

InChI Identifier

InChI=1S/C3H3FO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)

InChI Key

CXABZTLXNODUTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Alpha-haloketone
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organofluoride
Organohalogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organofluorine compound (CHEBI:55521 )
2-oxo monocarboxylic acid (CHEBI:55521 )

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	-0.42	ALOGPS
logP	0.14	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	18 m³·mol⁻¹	ChemAxon
Polarizability	7.4 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]+	122.402	30932474
DeepCCS	[M-H]-	119.598	30932474
DeepCCS	[M-2H]-	156.214	30932474
DeepCCS	[M+Na]+	130.973	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.6	32859911
AllCCS	[M+NH4]+	130.9	32859911
AllCCS	[M+Na]+	132.1	32859911
AllCCS	[M-H]-	120.8	32859911
AllCCS	[M+Na-2H]-	124.6	32859911
AllCCS	[M+HCOO]-	128.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Fluoro-2-oxopropanoic acid	OC(=O)C(=O)CF	1632.0	Standard polar	33892256
3-Fluoro-2-oxopropanoic acid	OC(=O)C(=O)CF	1202.7	Standard non polar	33892256
3-Fluoro-2-oxopropanoic acid	OC(=O)C(=O)CF	824.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Fluoro-2-oxopropanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C	1092.1	Semi standard non polar	33892256
3-Fluoro-2-oxopropanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C	1079.2	Standard non polar	33892256
3-Fluoro-2-oxopropanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C	1068.7	Standard polar	33892256
3-Fluoro-2-oxopropanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C(C)(C)C	1529.6	Semi standard non polar	33892256
3-Fluoro-2-oxopropanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C(C)(C)C	1464.1	Standard non polar	33892256
3-Fluoro-2-oxopropanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CF)O[Si](C)(C)C(C)(C)C	1434.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01po-9000000000-8b63b5fbccc267c043c0	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Fluoro-2-oxopropanoic acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 10V, Negative-QTOF	splash10-0udi-1900000000-2fe01644596273510387	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 20V, Negative-QTOF	splash10-014l-9000000000-83ab758c5f3e2599fdfc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 40V, Negative-QTOF	splash10-07bf-9000000000-c6c13d30c63dc6c2df25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 10V, Positive-QTOF	splash10-000i-9200000000-d4fe3986ccb121cdaea3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 20V, Positive-QTOF	splash10-03di-9000000000-9119b183979c08a825e0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Fluoro-2-oxopropanoic acid 40V, Positive-QTOF	splash10-03e9-9000000000-f892561616b4daa37a64	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	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	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	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	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	¹H NMR Spectrum (1D, 800 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	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

61263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67946

PDB ID

Not Available

ChEBI ID

55521

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 3-Fluoro-2-oxopropanoic acid (HMDB0252391)

MOL for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

3D MOL for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

3D SDF for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

3D-SDF for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

PDB for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

3D PDB for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

SMILES for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

INCHI for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

Structure for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

3D Structure for HMDB0252391 (3-Fluoro-2-oxopropanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra