NP-MRD: Showing NP-Card for N-Acetyl-L-phenylalanine (NP0001493)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:38:48 UTC

NP-MRD ID

NP0001493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-L-phenylalanine

Description

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’s (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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Acetylphenylalanine.mol
  Mrv1652305271900222D          

 15 15  0  0  0  0            999 V2000
   -1.6500   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.3572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
  1 11  2  0  0  0  0
  1 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001493

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.2258

> <EXACT_MASS>
207.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.206590010906925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-acetamido-3-phenylpropanoic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.8964616559999996

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.290533824652414

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.024367585343858

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9831528879816744

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
54.560100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyl-L-phenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Acetylphenylalanine.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.080  -0.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.770   0.667   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.540  -0.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -2.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -2.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540  -0.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -0.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850  -2.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -3.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540  -3.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.850   0.667   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.850  -2.001   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.540   2.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.080   2.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.770   3.334   0.000  0.00  0.00           C+0
CONECT    1    3   11   12                                                  
CONECT    2    3   13                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13   14   15    2                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000512
HETATM    1  C1  UNL     1       4.487   1.312  -0.013  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.125   1.019   0.501  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.773   1.613   1.558  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.246   0.114  -0.155  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.916  -0.178   0.340  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.059   0.302  -0.698  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.465   0.089  -0.368  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.134   1.086   0.329  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.462   0.996   0.693  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.158  -0.143   0.348  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.498  -1.142  -0.347  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.172  -1.044  -0.707  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.824  -1.614   0.630  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.810  -2.368   0.436  1.00  0.00           O  
HETATM   15  O3  UNL     1      -0.326  -2.227   1.126  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.559   2.381  -0.351  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.197   1.195   0.841  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.771   0.662  -0.858  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.597  -0.344  -1.023  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.780   0.428   1.267  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.220  -0.160  -1.684  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.107   1.390  -0.834  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.621   2.003   0.621  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.970   1.791   1.240  1.00  0.00           H  
HETATM   25  H10 UNL     1      -5.202  -0.214   0.635  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.034  -2.047  -0.626  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.645  -1.814  -1.248  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.666  -3.083   0.705  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   13   20
CONECT    6    7   21   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   14   15
CONECT   15   28
END

View in JSmol

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 Mass

207.2258 Da

Monoisotopic Mass

207.08954 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bombyx mori	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	171 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6450 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.93	Green, P. G., Hinz, R. S., Cullander, C., Yamane, G., & Guy, R. H. (1991). Lontophoretic delivery of amino acids and amino acid derivatives across the skin in vitro. Pharmaceutical research, 8(9), 1113-1120.

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

FoodDB 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

Good Scents ID

rw1265531

References

General References

Kucerova Z, Ticha M: Aromatic amino acids and their derivatives as ligands for the isolation of aspartic proteinases. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Apr 25;770(1-2):121-8. [PubMed:12013218 ]
Mach H, Middaugh CR, Lewis RV: Detection of proteins and phenol in DNA samples with second-derivative absorption spectroscopy. Anal Biochem. 1992 Jan;200(1):20-6. [PubMed:1375815 ]
Okajima K, Inoue M, Morino Y: Studies on the mechanism for renal elimination of N-acetylphenylalanine: its pathophysiologic significance in phenylketonuria. J Lab Clin Med. 1985 Jan;105(1):132-8. [PubMed:4038506 ]
Jellum E, Horn L, Thoresen O, Kvittingen EA, Stokke O: Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolism. Scand J Clin Lab Invest Suppl. 1986;184:21-6. [PubMed:3473611 ]

Showing NP-Card for N-Acetyl-L-phenylalanine (NP0001493)

MOL for NP0001493 (N-Acetyl-L-phenylalanine)

3D MOL for NP0001493 (N-Acetyl-L-phenylalanine)

3D SDF for NP0001493 (N-Acetyl-L-phenylalanine)

3D-SDF for NP0001493 (N-Acetyl-L-phenylalanine)

PDB for NP0001493 (N-Acetyl-L-phenylalanine)

3D PDB for NP0001493 (N-Acetyl-L-phenylalanine)

SMILES for NP0001493 (N-Acetyl-L-phenylalanine)

INCHI for NP0001493 (N-Acetyl-L-phenylalanine)

Structure for NP0001493 (N-Acetyl-L-phenylalanine)

3D Structure for NP0001493 (N-Acetyl-L-phenylalanine)