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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:54 UTC

HMDB ID

HMDB0000512

Secondary Accession Numbers

HMDB00512

Metabolite 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‚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 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>
HMDB0000512

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000512)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0000512)
Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

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

Source

Endogenous

Endogenous (HMDB: HMDB0000512)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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,PG ET AL. (1991)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	144.198	30932474
[M-H]-	Not Available	146.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000018

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.234	31661259
DarkChem	[M-H]-	145.206	31661259
AllCCS	[M+H]+	146.559	32859911
AllCCS	[M-H]-	146.378	32859911
DeepCCS	[M+H]+	142.468	30932474
DeepCCS	[M-H]-	140.073	30932474
DeepCCS	[M-2H]-	173.974	30932474
DeepCCS	[M+Na]+	148.672	30932474
AllCCS	[M+H]+	146.6	32859911
AllCCS	[M+H-H2O]+	142.6	32859911
AllCCS	[M+NH4]+	150.2	32859911
AllCCS	[M+Na]+	151.3	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	146.9	32859911
AllCCS	[M+HCOO]-	147.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-phenylalanine	CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	2997.4	Standard polar	33892256
N-Acetyl-L-phenylalanine	CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	1758.7	Standard non polar	33892256
N-Acetyl-L-phenylalanine	CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	1765.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-L-phenylalanine,1TMS,isomer #1	CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1805.5	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,1TMS,isomer #2	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	1800.2	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1799.6	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1862.1	Standard non polar	33892256
N-Acetyl-L-phenylalanine,2TMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2182.4	Standard polar	33892256
N-Acetyl-L-phenylalanine,1TBDMS,isomer #1	CC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2053.8	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,1TBDMS,isomer #2	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	2030.6	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2277.7	Semi standard non polar	33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2293.4	Standard non polar	33892256
N-Acetyl-L-phenylalanine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2455.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (2 TMS)	splash10-00kf-3980000000-205dc96635b498baa46c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (1 TMS)	splash10-00dl-3920000000-50af7cdc34df34b89e91	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized)	splash10-00kf-3980000000-205dc96635b498baa46c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized)	splash10-00dl-3920000000-50af7cdc34df34b89e91	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)	splash10-0fr7-1950000000-8c9c63efeb473bcf7625	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)	splash10-00dl-2920000000-f0ce2160cf1eb9d38d56	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-EI-TOF (Non-derivatized)	splash10-0f6x-2910000000-33afe725162942dc296a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-2c91eb9a78faef00e1da	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9110000000-e910d5b4824d2e88d697	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-L-phenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0900000000-9e69c187ac8560365826	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-0900000000-04559809a9c6261f18b6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ufr-5900000000-a8bb0fc573e6143527aa	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0a4i-0090000000-2dcdf0ed503251026e40	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-03di-2920000000-7447f1e30d868cae5af6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0lxy-8900000000-3b53da8f8106adfdd677	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0pbc-9400000000-1737db9a05bf29f3701a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4l-9100000000-f015dd2066ebbefec15a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0a4l-1960000000-20faf15c3d02bbe80ad2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00di-0900000000-891ecddb54dab32f4dce	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00di-1900000000-6867cba730dee8712265	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-00di-2900000000-2e77f5a51bec17ed674e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0udi-4900000000-c9aadc8231b14121aa8c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-02tc-0900000000-ac3b438665d0b035a7e2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0900000000-a426a7fbff06e9213f59	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-00di-0900000000-0d8dd7876525745785ff	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0fdo-6900000000-ad4d31f8b5e3e0474416	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ , negative-QTOF	splash10-0a4i-0090000000-2dcdf0ed503251026e40	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine LC-ESI-QQ , negative-QTOF	splash10-03di-2920000000-7447f1e30d868cae5af6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 10V, Positive-QTOF	splash10-0btc-2950000000-2865ae294df6193f5a75	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 20V, Positive-QTOF	splash10-044l-2900000000-1b1f3d364775a1619b26	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 40V, Positive-QTOF	splash10-0006-9200000000-9bb5ea6eb4c3ab49ee32	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 10V, Negative-QTOF	splash10-0a4i-2890000000-293238d6264d01ab86c4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 20V, Negative-QTOF	splash10-0900-5910000000-b912a04d31d0b03a8552	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-L-phenylalanine 40V, Negative-QTOF	splash10-052f-9200000000-1b69d466f84616cfe628	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1265531

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]

Showing metabocard for N-Acetyl-L-phenylalanine (HMDB0000512)

MOL for HMDB0000512 (N-Acetyl-L-phenylalanine)

3D MOL for HMDB0000512 (N-Acetyl-L-phenylalanine)

3D SDF for HMDB0000512 (N-Acetyl-L-phenylalanine)

3D-SDF for HMDB0000512 (N-Acetyl-L-phenylalanine)

PDB for HMDB0000512 (N-Acetyl-L-phenylalanine)

3D PDB for HMDB0000512 (N-Acetyl-L-phenylalanine)

SMILES for HMDB0000512 (N-Acetyl-L-phenylalanine)

INCHI for HMDB0000512 (N-Acetyl-L-phenylalanine)

Structure for HMDB0000512 (N-Acetyl-L-phenylalanine)

3D Structure for HMDB0000512 (N-Acetyl-L-phenylalanine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra