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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2021-09-11 07:53:57 UTC

Update Date

2022-07-18 23:53:32 UTC

HMDB ID

HMDB0250791

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Phenylalanine

Description

(±)-Phenylalanine, also known as F, 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 (±)-Phenylalanine is an odorless tasting compound (±)-Phenylalanine is found, on average, in the highest concentration within a few different foods, such as red bell peppers (Capsicum annuum), wheats (Triticum), and oats (Avena sativa) and in a lower concentration in carp breams (Abramis brama), common lings (Molva molva), and rainbow smelts (Osmerus mordax) (±)-Phenylalanine has also been detected, but not quantified in, several different foods, such as oil palms (Elaeis), ucuhubas (Virola surinamensis), lard, cocoa butter, and beer. This could make (±)-phenylalanine a potential biomarker for the consumption of these foods (±)-Phenylalanine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (±)-Phenylalanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). D-phenylalanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically D-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                                 07-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-OCT-17         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    7    8                                                       
CONECT    7    4    5    6                                                  
CONECT    8    6    9   10                                                  
CONECT    9    8   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Amino-beta-phenylpropionic acid	ChEBI
DL-Phenylalanine	ChEBI
F	ChEBI
Fenilalanina	ChEBI
PHE	ChEBI
Phenylalanin	ChEBI
a-Amino-b-phenylpropionate	Generator
a-Amino-b-phenylpropionic acid	Generator
alpha-Amino-beta-phenylpropionate	Generator
Α-amino-β-phenylpropionate	Generator
Α-amino-β-phenylpropionic acid	Generator
L-Isomer phenylalanine	MeSH
Endorphenyl	MeSH
L-Phenylalanine	MeSH
Phenylalanine	MeSH
Phenylalanine, L isomer	MeSH
Phenylalanine, L-isomer	MeSH

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

2-amino-3-phenylpropanoic acid

Traditional Name

phenylalanin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

InChI Key

COLNVLDHVKWLRT-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
Monocyclic benzene moiety
Benzenoid
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-amino acid (CHEBI:28044 )
aromatic amino acid (CHEBI:28044 )

Ontology

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	-1.4	ALOGPS
logP	-1.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.47	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	45.12 m³·mol⁻¹	ChemAxon
Polarizability	17.2 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
AllCCS	[M+H]+	136.8	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.1	32859911
AllCCS	[M-H]-	135.2	32859911
AllCCS	[M+Na-2H]-	136.3	32859911
AllCCS	[M+HCOO]-	137.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Phenylalanine	NC(CC1=CC=CC=C1)C(O)=O	2752.5	Standard polar	33892256
D-Phenylalanine	NC(CC1=CC=CC=C1)C(O)=O	1443.6	Standard non polar	33892256
D-Phenylalanine	NC(CC1=CC=CC=C1)C(O)=O	1814.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1628.6	Semi standard non polar	33892256
D-Phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1664.3	Standard non polar	33892256
D-Phenylalanine,2TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1948.3	Standard polar	33892256
D-Phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	1767.2	Semi standard non polar	33892256
D-Phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	1741.2	Standard non polar	33892256
D-Phenylalanine,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2119.8	Standard polar	33892256
D-Phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1829.5	Semi standard non polar	33892256
D-Phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1789.9	Standard non polar	33892256
D-Phenylalanine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1938.7	Standard polar	33892256
D-Phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2070.9	Semi standard non polar	33892256
D-Phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2086.0	Standard non polar	33892256
D-Phenylalanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2231.1	Standard polar	33892256
D-Phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2211.6	Semi standard non polar	33892256
D-Phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2161.7	Standard non polar	33892256
D-Phenylalanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2305.7	Standard polar	33892256
D-Phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2455.2	Semi standard non polar	33892256
D-Phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2394.5	Standard non polar	33892256
D-Phenylalanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2287.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-1880f5dae4360fab4947	2018-04-09	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-amino-3-phenylpropanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9300000000-4782928378caea601f9b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 35V, Positive-QTOF	splash10-00di-0900000000-58b3e0504dfeb61254e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 15V, Positive-QTOF	splash10-00di-0900000000-3cc5d610e74436c96c19	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 10V, Positive-QTOF	splash10-00di-0900000000-23ba76644ba103a54f61	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 6V, Negative-QTOF	splash10-01ot-0900000000-73ddf7eb5a4bdf975083	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 20V, Positive-QTOF	splash10-00di-0900000000-0ddf3e263974f732a55e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 20V, Positive-QTOF	splash10-00di-0900000000-b92f5a299928b72a0c15	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 40V, Positive-QTOF	splash10-0fb9-9300000000-a9cd15dd22c7c4c67549	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 6V, Positive-QTOF	splash10-00di-0900000000-a7383573a0010855fafa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 35V, Positive-QTOF	splash10-00di-0900000000-c990ee531fa1fddaad6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 10V, Positive-QTOF	splash10-00di-0900000000-cf6d59da738657f88ea6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 20V, Positive-QTOF	splash10-00di-2900000000-1a69a7a4025aa0ee4c77	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 25V, Positive-QTOF	splash10-00di-0900000000-6528c07eab2c79fd47e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 45V, Positive-QTOF	splash10-00di-0900000000-e98ddf2ca45f03019591	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 25V, Positive-QTOF	splash10-00di-0900000000-ceb4bd7dd8e1f71d5603	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 40V, Positive-QTOF	splash10-0udi-2900000000-00e5545144646ccd72e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 30V, Positive-QTOF	splash10-00di-0900000000-4858dd4ae63964321d5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 45V, Positive-QTOF	splash10-00di-0900000000-8819a69344a55991578f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 40V, Positive-QTOF	splash10-00di-0900000000-259adf768bdd45a62a93	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Phenylalanine 35V, Positive-QTOF	splash10-00di-1900000000-3436f16ff1c07507e613	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 10V, Positive-QTOF	splash10-00xs-0900000000-ff1b3ddc479e70084786	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 20V, Positive-QTOF	splash10-00di-1900000000-fc318d4d3cde828334e4	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 40V, Positive-QTOF	splash10-0006-9400000000-866eeb88a50bd575fa09	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 10V, Negative-QTOF	splash10-03di-0900000000-407406ada2082438a579	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 20V, Negative-QTOF	splash10-03dj-1900000000-347dc84ca7da32c5c176	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Phenylalanine 40V, Negative-QTOF	splash10-00dl-9600000000-a608d60e21d3beb49b12	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	152(100-450) uM	Adult (>18 years old)	Both	Sepsis	26847922	details

Associated Disorders and Diseases

Disease References

Sepsis
Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013245

KNApSAcK ID

Not Available

Chemspider ID

969

KEGG Compound ID

C02057

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylalanine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28044

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037691

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 ]

Enzymes

Enzyme Details

1. D-amino acid dehydrogenase

General function:: Not Available
Specific function:: Catalyzes the oxidative deamination of D-amino acids. Has broad substrate specificity; is mostly active on D-proline, and to a lesser extent, on several other D-amino acids such as D-alanine, D-phenylalanine and D-serine. Mediates electron transport from D-proline to coenzyme Q1 in vitro, and is involved in the electron transport chain from D-proline to the c-type cytochrome in vivo.
Gene Name:: DADA
Uniprot ID:: Q9ZKQ7
Molecular weight:: 46101.245

Showing metabocard for D-Phenylalanine (HMDB0250791)

MOL for HMDB0250791 (D-Phenylalanine)

3D MOL for HMDB0250791 (D-Phenylalanine)

3D SDF for HMDB0250791 (D-Phenylalanine)

3D-SDF for HMDB0250791 (D-Phenylalanine)

PDB for HMDB0250791 (D-Phenylalanine)

3D PDB for HMDB0250791 (D-Phenylalanine)

SMILES for HMDB0250791 (D-Phenylalanine)

INCHI for HMDB0250791 (D-Phenylalanine)

Structure for HMDB0250791 (D-Phenylalanine)

3D Structure for HMDB0250791 (D-Phenylalanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes