ChemFOnt: Showing chemical card for N-Acetyl-L-phenylalanine (CFc000000392)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:46 UTC

Chemfont ID

CFc000000392

Molecule Identification

Common Name

N-Acetyl-L-phenylalanine

Definition

N-Acetyl-L-phenylalanine or N-Acetylphenylalanine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-phenylalanine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-phenylalanine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-phenylalanine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylphenylalanine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free phenylalanine can also occur. In particular, N-Acetyl-L-phenylalanine can be biosynthesized from L-phenylalanine and acetyl-CoA by the enzyme phenylalanine N-acetyltransferase (EC 2.3.1.53). N-Acetyl-L-phenylalanine is a potential uremic toxin and is considered as a hazardous amphipathic metabolite of phenylalanine (PMID: 4038506 ). Many N-acetylamino acids, including N-acetylphenylalanine, are classified as uremic toxins (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-Acetyl-L-phenylalanine appears in large amount in urine of patients with phenylketonuria (PKU), which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine (PMID: 3473611 ). N-Acetyl-L-phenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] which is found in the phenylalanine metabolism pathway. N-Acetyl-L-phenylalanine is produced for medical, feed, and nutritional applications such as in the preparation of aspartame. Afalanine (N-Acetyl-DL-phenylalanine) is also approved for use as an antidepressant.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Acetyl-L-phenylalanine	ChEBI
Acetylphenylalanine	ChEBI
L-N-Acetylphenylalanine	ChEBI
N-Acetylphenylalanine	ChEBI
N-Acetyl-3-phenyl-L-alanine	HMDB
N-Acetyl-L-phenalanine	HMDB
N-Acetylphenylalanine, (D,L)-isomer, 3H-labeled	HMDB
N-Acetylphenylalanine, (L)-isomer	HMDB
N-Acetylphenylalanine, (L)-isomer, 3H-labeled	HMDB
N-Acetylphenylalanine, (D)-isomer	HMDB

Chemical Formula

C₁₁H₁₃NO₃

Average Molecular Weight

207.2258

Monoisotopic Molecular Weight

207.089543287

IUPAC Name

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

Traditional Name

acetyl-L-phenylalanine

CAS Registry Number

2018-61-3

SMILES

CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1

InChI Key

CBQJSKKFNMDLON-JTQLQIEISA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:16259 )
N-acetylphenylalanine (CHEBI:16259 )
N-acyl-L-phenylalanine (CHEBI:16259 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000512)
Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0000512)

Source

Endogenous

Endogenous (HMDB: HMDB0000512)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	1.11	ALOGPS
logP	0.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.56 m³·mol⁻¹	ChemAxon
Polarizability	21.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000512

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022084

KNApSAcK ID

Not Available

Chemspider ID

67404

KEGG Compound ID

C03519

BioCyc ID

CPD-439

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5498

PubChem Compound

74839

PDB ID

Not Available

ChEBI ID

16259

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Borovicka, Milos; Cervinka, Otakar; Gajewski, Karel; Lukac, Juraj. Isolation of optically pure N-acetyl-L-phenylalanine after enantioselective hydrogenation of N-acetamidocinnamic acid. Czech. (1985), 2 pp.

Showing chemical card for N-Acetyl-L-phenylalanine (CFc000000392)

MOL for CFc000000392 (N-Acetyl-L-phenylalanine)

3D MOL for CFc000000392 (N-Acetyl-L-phenylalanine)

3D SDF for CFc000000392 (N-Acetyl-L-phenylalanine)

3D-SDF for CFc000000392 (N-Acetyl-L-phenylalanine)

PDB for CFc000000392 (N-Acetyl-L-phenylalanine)

3D PDB for CFc000000392 (N-Acetyl-L-phenylalanine)

SMILES for CFc000000392 (N-Acetyl-L-phenylalanine)

INCHI for CFc000000392 (N-Acetyl-L-phenylalanine)

Structure for CFc000000392 (N-Acetyl-L-phenylalanine)

3D Structure for CFc000000392 (N-Acetyl-L-phenylalanine)