MiMeDB: Showing metabocard for N-a-Acetyl-L-arginine (MMDBc0000432)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:37 UTC

Update Date

2024-10-10 01:12:30 UTC

Metabolite ID

MMDBc0000432

Metabolite Identification

Common Name

N-a-Acetyl-L-arginine

Description

N-alpha-Acetyl-L-arginine, also known as N-alpha-acetylarginine, 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-Acetylarginine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylarginine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-arginine. 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-acetylarginine 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 arginine can also occur. Many N-acetylamino acids, including N-acetylarginine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ; PMID: 7777105 ). 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-alpha-Acetyl-L-arginine serum levels (and other guanidino compounds) were elevated of all the hyperargininemic patients are higher than the normal range. Untreated hyperargininemic patients have the highest guanidino compound levels in cerebrospinal fluid. N-alpha-Acetyl-L-arginine is also increased in the urine or hyperargininemic patients. N-alpha-Acetyl-L-arginine is one of the guanidino compounds found elevated in the serum of hemodialyzed renal insufficient (uremic) pediatric patients.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0004620
     RDKit          3D
N-a-Acetyl-L-arginine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.5215   -1.0908   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4456   -0.0797   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7744    1.1337   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.4103   -0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    0.6011   -0.8914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2546    0.7279    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.5006    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901   -1.0588   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -0.0846   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.1871    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8222   -0.7588    1.7171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.5273    1.4056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.4145   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -0.5582   -2.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    1.2821   -2.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9553   -1.0459    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -0.9911   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -2.0948   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.4037   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    1.5753   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289    1.1620    1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    1.5641    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.3030    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -1.3041    1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -1.9232    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.4774   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995    0.3750   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485   -1.7655    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406    2.2152    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.9085    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.1767   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END


  Mrv0541 02231215522D          

 15 14  0  0  1  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000432

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H](CCCNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N4O3/c1-5(13)12-6(7(14)15)3-2-4-11-8(9)10/h6H,2-4H2,1H3,(H,12,13)(H,14,15)(H4,9,10,11)/t6-/m0/s1

> <INCHI_KEY>
SNEIUMQYRCDYCH-LURJTMIESA-N

> <FORMULA>
C8H16N4O3

> <MOLECULAR_WEIGHT>
216.2376

> <EXACT_MASS>
216.122240398

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.035673991789412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-carbamimidamido-2-acetamidopentanoic acid

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-3.3150728885286282

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.729376673324762

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6821119170709866

> <JCHEM_PKA_STRONGEST_BASIC>
12.244879969649634

> <JCHEM_POLAR_SURFACE_AREA>
128.3

> <JCHEM_REFRACTIVITY>
63.3669

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N~2~-acetyl-L-arginine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004620
     RDKit          3D
N-a-Acetyl-L-arginine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.5215   -1.0908   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4456   -0.0797   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7744    1.1337   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.4103   -0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    0.6011   -0.8914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2546    0.7279    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.5006    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901   -1.0588   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -0.0846   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.1871    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8222   -0.7588    1.7171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.5273    1.4056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.4145   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -0.5582   -2.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    1.2821   -2.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9553   -1.0459    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -0.9911   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -2.0948   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.4037   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    1.5753   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289    1.1620    1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    1.5641    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.3030    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -1.3041    1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -1.9232    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.4774   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995    0.3750   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485   -1.7655    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406    2.2152    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.9085    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.1767   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596   6.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.930   4.001   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      13.598   4.771   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      16.266   4.771   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      14.932   2.461   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.264   6.311   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.597   7.081   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.930   7.081   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0004620
HETATM    1  C1  UNL     1      -4.522  -1.091  -0.566  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.446  -0.080  -0.728  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.774   1.134  -0.869  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.081  -0.410  -0.731  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.046   0.601  -0.891  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.255   0.728   0.355  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.426  -0.501   0.845  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.490  -1.059  -0.031  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.573  -0.085  -0.168  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.331   0.187   1.012  1.00  0.00           C  
HETATM   11  N3  UNL     1       3.822  -0.759   1.717  1.00  0.00           N  
HETATM   12  N4  UNL     1       3.541   1.527   1.406  1.00  0.00           N  
HETATM   13  C8  UNL     1      -0.255   0.414  -2.087  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.459  -0.558  -2.871  1.00  0.00           O  
HETATM   15  O3  UNL     1       0.760   1.282  -2.445  1.00  0.00           O  
HETATM   16  H1  UNL     1      -4.955  -1.046   0.453  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.286  -0.991  -1.359  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.042  -2.095  -0.693  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.777  -1.404  -0.616  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.648   1.575  -0.996  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.929   1.162   1.149  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.501   1.564   0.176  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.819  -0.303   1.890  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.359  -1.304   1.003  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.990  -1.923   0.528  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.165  -1.477  -0.977  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.800   0.375  -1.044  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.748  -1.765   1.550  1.00  0.00           H  
HETATM   29  H14 UNL     1       2.741   2.215   1.457  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.486   1.909   1.664  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.640   2.177  -2.860  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   23   24
CONECT    8    9   25   26
CONECT    9   10   27
CONECT   10   11   11   12
CONECT   11   28
CONECT   12   29   30
CONECT   13   14   14   15
CONECT   15   31
END

HMDB0004620
     RDKit          3D
N-a-Acetyl-L-arginine
 31 30  0  0  0  0  0  0  0  0999 V2000
   -4.5215   -1.0908   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4456   -0.0797   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7744    1.1337   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.4103   -0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0459    0.6011   -0.8914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2546    0.7279    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.5006    0.8447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901   -1.0588   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -0.0846   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314    0.1871    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8222   -0.7588    1.7171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407    1.5273    1.4056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.4145   -2.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -0.5582   -2.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    1.2821   -2.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9553   -1.0459    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -0.9911   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -2.0948   -0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771   -1.4037   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    1.5753   -0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289    1.1620    1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005    1.5641    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.3030    1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -1.3041    1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -1.9232    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.4774   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995    0.3750   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485   -1.7655    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406    2.2152    1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.9085    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    2.1767   -2.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 15 31  1  0
M  END

Synonyms

Value	Source
N-Ac-L-arg-OH	ChEBI
N-Acetyl-L-arginine	ChEBI
N(2)-Acetyl-L-arginine	ChEBI
N-alpha-Acetyl-L-arginine	HMDB
N-alpha-L-Acetyl-arginine	HMDB
N2-Acetyl-L-arginine	HMDB
Acetyl arginine	MeSH, HMDB
N-alpha-Acetylarginine	MeSH, HMDB
N(a)-Acetyl-L-arginine	Generator, HMDB
N(Α)-acetyl-L-arginine	Generator, HMDB
N-a-L-Acetyl-arginine	Generator, HMDB
N-Α-L-acetyl-arginine	Generator, HMDB

Molecular Formula

C₈H₁₆N₄O₃

Average Mass

216.2376

Monoisotopic Mass

216.122240398

IUPAC Name

(2S)-5-carbamimidamido-2-acetamidopentanoic acid

Traditional Name

N~2~-acetyl-L-arginine

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C8H16N4O3/c1-5(13)12-6(7(14)15)3-2-4-11-8(9)10/h6H,2-4H2,1H3,(H,12,13)(H,14,15)(H4,9,10,11)/t6-/m0/s1

InChI Key

SNEIUMQYRCDYCH-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Fatty acid
Acetamide
Carboxamide group
Guanidine
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:40521 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	12.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.37 m³·mol⁻¹	ChemAxon
Polarizability	22.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-1ceaef8ce37a7b0824d7	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9520000000-c079d35b9012a55883d2	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-053u-9800000000-21b92cfd48ed4a2653df	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-58b164576b6245ba5e98	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-58a41f9d8b6b341edbad	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-01c0-2940000000-8c72ed0fc62303b7f4a2	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-1940000000-495d7eb88df38bf7a81f	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03mi-2900000000-a1ce241787b062182472	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9400000000-d6685c90df9e6a8f2a03	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-2930000000-c8a853d3dffa744063ac	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-4900000000-99f3a540de4819b0d14e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-e57d664a81b0164998d5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ba-0950000000-2fea8c9022bec91ce56b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008a-2910000000-69304c511117e4cfb10c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-368bed42fdebf4188927	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0490000000-399f9d9369bbdc8e156f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0900-1900000000-bd5e452ef23574028f09	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9400000000-38ff35c82244b5d8dc7d	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Hyperargininemia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	3433275
Uremia	Increased	Association	Human Blood	HMDB	12675874

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	8	Human feces; Human ; Human stool; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	3	Human feces; Human stool; Human urine; Human saliva; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Shoot	Malus pumila	FooDB	DUKE
Plant	Shoot	Eriobotrya japonica	FooDB	DUKE

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.5		0.0	1.0	uM	Adult (>18 years old)	Not Specified	Hyperargininemia	HMDB	3433275
Human Blood	Detected and Quantified	1.520	0.660			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	0.0838	0.115			uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.15		0.07	0.23	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	3433275
Human Blood	Detected and Quantified	1.25	0.28			uM	Adult (>18 years old)	Both	Normal	HMDB	3433275
Human Urine	Detected and Quantified	1.38		0.64	2.12	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	18818040
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0004620

DrugBank ID

DB01985

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023383

KNApSAcK ID

Not Available

Chemspider ID

60752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67427

PDB ID

Not Available

ChEBI ID

40521

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. doi: 10.1203/00006450-199003000-00020. [PubMed:1690873 ]
Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. doi: 10.1620/tjem.153.197. [PubMed:3433275 ]
Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. doi: 10.1016/0009-8981(85)90120-2. [PubMed:3987036 ]
De Deyn PP, Robitaille P, Vanasse M, Qureshi IA, Marescau B: Serum guanidino compound levels in uremic pediatric patients treated with hemodialysis or continuous cycle peritoneal dialysis. Correlations between nerve conduction velocities and altered guanidino compound concentrations. Nephron. 1995;69(4):411-7. doi: 10.1159/000188511. [PubMed:7777105 ]
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. doi: 10.1086/500563. Epub 2006 Jan 18. [PubMed:16465618 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for N-a-Acetyl-L-arginine (MMDBc0000432)

MOL for #<Metabolite:0x00007fdb0eeecc80>

3D MOL for #<Metabolite:0x00007fdb0eeecc80>

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3D-SDF for #<Metabolite:0x00007fdb0eeecc80>

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3D PDB for #<Metabolite:0x00007fdb0eeecc80>

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INCHI for #<Metabolite:0x00007fdb0eeecc80>

Structure for #<Metabolite:0x00007fdb0eeecc80>

3D Structure for #<Metabolite:0x00007fdb0eeecc80>