Showing metabocard for Acetylglycine (MMDBc0000353)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:58 UTC
Update Date2022-08-31 06:02:31 UTC
Metabolite IDMMDBc0000353
Metabolite Identification
Common NameAcetylglycine
DescriptionN-Acetyl-glycine or N-Acetylglycine, 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-Acetylglycine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylglycine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid glycine. 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-acetylglycine 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 glycine can also occur. In particular, N-Acetylglycine can be biosynthesized from glycine and acetyl-CoA by the enzyme glycine N-acyltransferase (GLYAT) (EC 2.3.1.13). Excessive amounts N-acetyl amino acids including N-acetylglycine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, Nacetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylglycine, are classified as uremic toxins if present in high abundance in the serum or plasma (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 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be1b56c90>


  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812    1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.1105    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000560be1b56c90>

HMDB0000532
     RDKit          3D
Acetylglycine
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.6713    0.3317    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630    0.7184    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.9057   -0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2615    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.1352   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -0.9927   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -2.1427    0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021   -0.7618   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.1270    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.6224    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2118   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -1.2524    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.4950   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    0.9671    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    0.1416   -0.5106 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
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3D SDF for #<Metabolite:0x0000560be1b56c90>


  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812    1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.1105    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000353

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)

> <INCHI_KEY>
OKJIRPAQVSHGFK-UHFFFAOYSA-N

> <FORMULA>
C4H7NO3

> <MOLECULAR_WEIGHT>
117.1033

> <EXACT_MASS>
117.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.690091704986068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamidoacetic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-1.3286289540000003

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.581933746898102

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.772480582340469

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0460057413187704

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
25.4472

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aceturate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000560be1b56c90>

HMDB0000532
     RDKit          3D
Acetylglycine
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.6713    0.3317    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630    0.7184    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.9057   -0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2615    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.1352   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -0.9927   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -2.1427    0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021   -0.7618   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.1270    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.6224    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2118   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -1.2524    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.4950   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    0.9671    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    0.1416   -0.5106 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
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PDB for #<Metabolite:0x0000560be1b56c90>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.978   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.312   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.978  -0.206   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x0000560be1b56c90>

COMPND    HMDB0000532
HETATM    1  C1  UNL     1      -2.671   0.332   0.317  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.263   0.718   0.036  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.952   1.906  -0.261  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.242  -0.261   0.099  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.119   0.135  -0.179  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.065  -0.993  -0.074  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.683  -2.143   0.225  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.402  -0.762  -0.312  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.143   1.127   0.958  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.694  -0.622   0.885  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.232   0.212  -0.633  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.500  -1.252   0.346  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.176   0.495  -1.244  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.455   0.967   0.493  1.00  0.00           H  
HETATM   15  H7  UNL     1       3.798   0.142  -0.511  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12
CONECT    5    6   13   14
CONECT    6    7    7    8
CONECT    8   15
END
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SMILES for #<Metabolite:0x0000560be1b56c90>

CC(=O)NCC(O)=O
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INCHI for #<Metabolite:0x0000560be1b56c90>

InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
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Synonyms
ValueSource
Ac-gly-OHChEBI
Acetamidoacetic acidChEBI
Aceturic acidChEBI
Acetylamino-acetic acidChEBI
Acetylaminoacetic acidChEBI
Ethanoylaminoethanoic acidChEBI
AcetamidoacetateGenerator
AcetateGenerator
Acetic acidGenerator
Acetylamino-acetateGenerator
AcetylaminoacetateGenerator
EthanoylaminoethanoateGenerator
15N-Acetylglycine a-radicalHMDB
2-AcetamidoacetateHMDB
2-Acetamidoacetic acidHMDB
Ac glyHMDB
AceturateHMDB
AcetylglycocollHMDB
N-Acetyl-glycineHMDB
N-AcetylglycineHMDB
N-Acetylglycine sodium saltHMDB
AcetylglycinateHMDB
AcetylglycineChEBI
Molecular FormulaC4H7NO3
Average Mass117.1033
Monoisotopic Mass117.042593095
IUPAC Name2-acetamidoacetic acid
Traditional Nameaceturate
CAS Registry NumberNot Available
SMILES
CC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
InChI KeyOKJIRPAQVSHGFK-UHFFFAOYSA-N