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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:26:39 UTC

Update Date

2021-09-26 22:55:29 UTC

HMDB ID

HMDB0246423

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Fluoro-L-phenylalanine

Description

4-fluorophenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 4-fluorophenylalanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-fluoro-l-phenylalanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Fluoro-L-phenylalanine 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

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  F   UNK     0       1.334   3.850   0.000  0.00  0.00           F+0
HETATM   11  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    4   10                                                  
CONECT    8    5    9   11                                                  
CONECT    9    8   12   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
DL-Fluorophenylalanine	ChEBI
DL-p-Fluorophenylalanine	ChEBI
p-Fluoro-DL-phenylalanine	ChEBI
p-Fluorophenylalanine	ChEBI
4 Fluorophenylalanine	MeSH
Fluorophenylalanine, p	MeSH
p Fluorophenylalanine	MeSH
Para fluorophenylalanine	MeSH
Para-fluorophenylalanine	MeSH
4-Fluorophenylalanine	MeSH

Chemical Formula

C₉H₁₀FNO₂

Average Molecular Weight

183.182

Monoisotopic Molecular Weight

183.069556729

IUPAC Name

2-amino-3-(4-fluorophenyl)propanoic acid

Traditional Name

DL-P-fluorophenylalanine

CAS Registry Number

Not Available

SMILES

NC(CC1=CC=C(F)C=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

InChI Key

XWHHYOYVRVGJJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
Aralkylamine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Organofluoride
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:84060 )
monofluorobenzenes (CHEBI:84060 )
phenylalanine derivative (CHEBI:84060 )
a small molecule (CPD0-1900 )

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	-1.5	ALOGPS
logP	-1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.33 m³·mol⁻¹	ChemAxon
Polarizability	17.31 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]+	136.583	30932474
DeepCCS	[M-H]-	132.755	30932474
DeepCCS	[M-2H]-	170.121	30932474
DeepCCS	[M+Na]+	145.66	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.3	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	139.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Fluoro-L-phenylalanine	NC(CC1=CC=C(F)C=C1)C(O)=O	2715.6	Standard polar	33892256
4-Fluoro-L-phenylalanine	NC(CC1=CC=C(F)C=C1)C(O)=O	1418.5	Standard non polar	33892256
4-Fluoro-L-phenylalanine	NC(CC1=CC=C(F)C=C1)C(O)=O	1705.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Fluoro-L-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C	1639.1	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C	1689.0	Standard non polar	33892256
4-Fluoro-L-phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C	1876.3	Standard polar	33892256
4-Fluoro-L-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C	1803.5	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C	1765.4	Standard non polar	33892256
4-Fluoro-L-phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C	2046.6	Standard polar	33892256
4-Fluoro-L-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1844.4	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1817.2	Standard non polar	33892256
4-Fluoro-L-phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1843.9	Standard polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2091.9	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2104.7	Standard non polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=C(F)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2159.9	Standard polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2247.8	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2163.2	Standard non polar	33892256
4-Fluoro-L-phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=C(F)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2237.1	Standard polar	33892256
4-Fluoro-L-phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2509.0	Semi standard non polar	33892256
4-Fluoro-L-phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2405.5	Standard non polar	33892256
4-Fluoro-L-phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(F)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2192.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-5900000000-0df8d3693fddbe5267c3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Fluoro-L-phenylalanine 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 - 4-Fluoro-L-phenylalanine 10V, Positive-QTOF	splash10-0019-0900000000-1266c4f2c50072ce8205	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 20V, Positive-QTOF	splash10-000i-0900000000-9c02629c9440a25b8acd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 40V, Positive-QTOF	splash10-044r-5900000000-95b3c3d4f36975a68d83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 10V, Negative-QTOF	splash10-001i-0900000000-3ded43b1e218cbe8cd6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 20V, Negative-QTOF	splash10-001i-0900000000-2533d09ee1040c0e04f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 40V, Negative-QTOF	splash10-00di-7900000000-48a61c63791813f2a1bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 10V, Positive-QTOF	splash10-000i-0900000000-0b2141fa2c6e4a96d753	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 20V, Positive-QTOF	splash10-000i-0900000000-67c3868ad6de4d4c7479	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 40V, Positive-QTOF	splash10-066r-3900000000-b75a111aaa591f9dc1e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 10V, Negative-QTOF	splash10-00lr-1900000000-40539908066026f2c941	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 20V, Negative-QTOF	splash10-00di-2900000000-952c1a1103dbf94f05b6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Fluoro-L-phenylalanine 40V, Negative-QTOF	splash10-0002-9200000000-460321473d05573ceaba	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	¹³C NMR Spectrum (1D, 1000 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	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	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	¹H NMR Spectrum (1D, 900 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

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

4493

KEGG Compound ID

C11217

BioCyc ID

CPD0-1900

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4654

PDB ID

Not Available

ChEBI ID

84060

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-Fluoro-L-phenylalanine (HMDB0246423)

MOL for HMDB0246423 (4-Fluoro-L-phenylalanine)

3D MOL for HMDB0246423 (4-Fluoro-L-phenylalanine)

3D SDF for HMDB0246423 (4-Fluoro-L-phenylalanine)

3D-SDF for HMDB0246423 (4-Fluoro-L-phenylalanine)

PDB for HMDB0246423 (4-Fluoro-L-phenylalanine)

3D PDB for HMDB0246423 (4-Fluoro-L-phenylalanine)

SMILES for HMDB0246423 (4-Fluoro-L-phenylalanine)

INCHI for HMDB0246423 (4-Fluoro-L-phenylalanine)

Structure for HMDB0246423 (4-Fluoro-L-phenylalanine)

3D Structure for HMDB0246423 (4-Fluoro-L-phenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra