AFCDB: (±)-Phenylalanine (FDB013245)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:36 UTC

Update date

2019-11-26 03:08:11 UTC

Primary ID

FDB013245

Secondary Accession Numbers

FDB014705

Chemical Information

FooDB Name

(±)-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 dills (Anethum graveolens), greater sturgeons (Acipenser), and gadiformes (Gadiformes) (±)-Phenylalanine has also been detected, but not quantified in, several different foods, such as tallow, sesame oil, sunflower oil, rapeseed oil, and lard. This could make (±)-phenylalanine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-Phenylalanine.

CAS Number

150-30-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.14 g/L	ALOGPS
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

Chemical Formula

C9H11NO2

IUPAC name

2-amino-3-phenylpropanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

Classification

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

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.44%; H 6.71%; N 8.48%; O 19.37%	DFC
Melting Point	Mp 318-320° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	14.2 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-1.44	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00dl-9300000000-4782928378caea601f9b	2014-09-20	View Spectrum
Predicted GC-MS	(±)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-1880f5dae4360fab4947	Spectrum
Predicted GC-MS	(±)-Phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(±)-Phenylalanine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(±)-Phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(±)-Phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(±)-Phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C02057

Pubchem Compound ID

994

Pubchem Substance ID

Not Available

ChEBI ID

28044

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JVC81-S:HQC15-W

EAFUS ID

2994

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1037691

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).

(±)-Phenylalanine (FDB013245)

Structure for FDB013245 ((±)-Phenylalanine)