ChemFOnt: Showing chemical card for 2-amino-3-phenylpropanoic acid (CFc000140152)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:16:05 UTC

Chemfont ID

CFc000140152

Molecule Identification

Common Name

2-amino-3-phenylpropanoic acid

Definition

L-Phenylalanine, also known as Phe or 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. L-Phenylalanine is a very strong basic compound (based on its pKa). L-Phenylalanine exists in all living species, ranging from bacteria to humans. Outside of the human body, L-Phenylalanine has been detected, but not quantified in, watermelons. This could make L-phenylalanine a potential biomarker for the consumption of these foods. L-Phenylalanine is a potentially toxic compound. L-Phenylalanine, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, gout, dengue fever, and eosinophilic esophagitis; L-phenylalanine has also been linked to the inborn metabolic disorder maple syrup urine disease. The L-enantiomer oL-Phenylalanine phenylalanine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-Amino-3-phenylpropionic acid	ChEBI
(S)-alpha-Amino-beta-phenylpropionic acid	ChEBI
3-Phenyl-L-alanine	ChEBI
beta-Phenyl-L-alanine	ChEBI
F	ChEBI
Phe	ChEBI
PHENYLALANINE	ChEBI
(S)-2-Amino-3-phenylpropionate	Generator
(S)-a-Amino-b-phenylpropionate	Generator
(S)-a-Amino-b-phenylpropionic acid	Generator
(S)-alpha-Amino-beta-phenylpropionate	Generator
(S)-Α-amino-β-phenylpropionate	Generator
(S)-Α-amino-β-phenylpropionic acid	Generator
b-Phenyl-L-alanine	Generator
Β-phenyl-L-alanine	Generator
(-)-beta-Phenylalanine	HMDB
(L)-Phenylalanine	HMDB
(S)-(-)-Phenylalanine	HMDB
(S)-2-Amino-3-phenylpropanoate	HMDB
(S)-2-Amino-3-phenylpropanoic acid	HMDB
(S)-alpha-Amino-benzenepropanoate	HMDB
(S)-alpha-Amino-benzenepropanoic acid	HMDB
(S)-alpha-Aminobenzenepropanoate	HMDB
(S)-alpha-Aminobenzenepropanoic acid	HMDB
(S)-alpha-Aminohydrocinnamate	HMDB
(S)-alpha-Aminohydrocinnamic acid	HMDB
(S)-Phenylalanine	HMDB
alpha-Aminohydrocinnamate	HMDB
alpha-Aminohydrocinnamic acid	HMDB
beta-Phenyl-alpha-alanine	HMDB
beta-Phenylalanine	HMDB
L-2-Amino-3-phenylpropionate	HMDB
L-2-Amino-3-phenylpropionic acid	HMDB
Phenyl-alanine	HMDB
Phenylalamine	HMDB
L-Isomer phenylalanine	HMDB
Phenylalanine, L isomer	HMDB
Phenylalanine, L-isomer	HMDB
Endorphenyl	HMDB
(6S)-Tetrahydrofolate	HMDB
(6S)-Tetrahydrofolic acid	HMDB
(6S)-THFA	HMDB
5,6,7,8-Tetrahydrofolate	HMDB
Tetrahydrofolate	HMDB
THF	HMDB
5,6,7,8-Tetrahydrofolic acid	HMDB

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

(2S)-2-amino-3-phenylpropanoic acid

Traditional Name

L-phenylalanine

CAS Registry Number

63-91-2

SMILES

N[C@@H](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)/t8-/m0/s1

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17295 )
L-alpha-amino acid (CHEBI:17295 )
phenylalanine (CHEBI:17295 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17295 )
Common amino acids (C00079 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

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	17.03 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