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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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.0864 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	669.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	292.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	664.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	717.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	219.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	773.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	200.7 seconds	40023050

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

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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes