Showing metabocard for Guanidoacetic acid (MMDBc0000496)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:05 UTC
Update Date2024-09-29 15:09:28 UTC
Metabolite IDMMDBc0000496
Metabolite Identification
Common NameGuanidoacetic acid
DescriptionGuanidoacetic acid (GAA), also known as guanidinoacetate or glycocyamine, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Guanidinoacetic acid was first prepared in 1861 by Adolph Strecker by reaction of cyanamide with glycine in aqueous solution. Manufactured guanidinoacetic acid is primarily used a feed additive approved by EFSA in poultry farming (for fattening), and pigs for fattening. Guanidoacetic acid exists naturally in all vertebrates. It is formed primarily in the kidneys by transferring the guanidine group of L-arginine to the amino acid glycine via the enzyme known as L-Arg:Gly-amidinotransferase (AGAT). In a further step, guanidinoacetate is methylated to generate creatine using S-adenosyl methionine (as the methyl donor) via the enzyme known as guanidinoacetate N-methyltransferase (GAMT). The resulting creatine is released into the bloodstream. Elevated levels of guanidoacetic acid are a characteristic of an inborn metabolic disorder known as Guanidinoacetate Methyltransferase (GAMT) Deficiency. GAMT converts guanidinoacetate to creatine and deficiency of this enzyme results in creatine depletion and accumulation of guanidinoacetate The disorder is transmitted in an autosomal recessive fashion and is localized to mutations on chromosome 19p13.3. GAMT deficiency is characterized by developmental arrest, medication-resistant epilepsy (myoclonic, generalized tonic-clonic, partial complex, atonic), severe speech impairment, progressive dystonia, dyskinesias, hypotonia, ataxia, and autistic-like behavior.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923b6539a0>


  Mrv1652305271900142D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -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:0x00007f923b6539a0>

HMDB0000128
     RDKit          3D
Guanidoacetic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0620   -1.1972   -0.4757 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1646   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    1.1153   -0.4704 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4159   -0.2839    0.9085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    0.2128    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521   -0.5078   -0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   -1.4472   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -0.1768   -0.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450   -2.1749   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    1.7707    0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    1.4305   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370   -0.7748    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673    0.1169    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238    1.3269    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969    0.7540   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 10  1  0
  3 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:0x00007f923b6539a0>


  Mrv1652305271900142D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -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>
MMDBc0000496

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=N)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)

> <INCHI_KEY>
BPMFZUMJYQTVII-UHFFFAOYSA-N

> <FORMULA>
C3H7N3O2

> <MOLECULAR_WEIGHT>
117.1066

> <EXACT_MASS>
117.053826483

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.53697099662325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-carbamimidamidoacetic acid

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-3.1262055894355907

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3686966251675314

> <JCHEM_PKA_STRONGEST_BASIC>
12.241335630709775

> <JCHEM_POLAR_SURFACE_AREA>
99.20000000000002

> <JCHEM_REFRACTIVITY>
36.718

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycocyamine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f923b6539a0>

HMDB0000128
     RDKit          3D
Guanidoacetic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0620   -1.1972   -0.4757 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1646   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    1.1153   -0.4704 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4159   -0.2839    0.9085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169    0.2128    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521   -0.5078   -0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   -1.4472   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -0.1768   -0.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450   -2.1749   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750    1.7707    0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7468    1.4305   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6370   -0.7748    1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673    0.1169    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238    1.3269    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969    0.7540   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 10  1  0
  3 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:0x00007f923b6539a0>

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  N   UNK     0      -0.357   1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.976   3.644   0.000  0.00  0.00           N+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       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -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:0x00007f923b6539a0>

COMPND    HMDB0000128
HETATM    1  N1  UNL     1       2.062  -1.197  -0.476  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.459  -0.165  -0.022  1.00  0.00           C  
HETATM    3  N2  UNL     1       1.856   1.115  -0.470  1.00  0.00           N  
HETATM    4  N3  UNL     1       0.416  -0.284   0.909  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.917   0.213   0.717  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.652  -0.508  -0.325  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.088  -1.447  -0.931  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.952  -0.177  -0.654  1.00  0.00           O  
HETATM    9  H1  UNL     1       1.845  -2.175  -0.210  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.275   1.771   0.220  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.747   1.431  -1.472  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.637  -0.775   1.808  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.467   0.117   1.673  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.924   1.327   0.515  1.00  0.00           H  
HETATM   15  H7  UNL     1      -3.297   0.754  -0.748  1.00  0.00           H  
CONECT    1    2    2    9
CONECT    2    3    4
CONECT    3   10   11
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:0x00007f923b6539a0>

NC(=N)NCC(O)=O
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INCHI for #<Metabolite:0x00007f923b6539a0>

InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)
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Synonyms
ValueSource
GlycocyamineChEBI
GuanidinoacetateChEBI
N-(Carbamimidoyl)glycineChEBI
N-[Amino(imino)methyl]glycineChEBI
N-AmidinoglycineChEBI
Guanidinoacetic acidKegg
GuanidoacetateGenerator
(Carboxymethyl)-guanidineHMDB
2-[[Amino(imino)methyl]amino]acetateHMDB
2-[[Amino(imino)methyl]amino]acetic acidHMDB
a-GuanidinoacetateHMDB
a-Guanidinoacetic acidHMDB
alpha-GuanidinoacetateHMDB
alpha-Guanidinoacetic acidHMDB
b-GuanidinoacetateHMDB
b-Guanidinoacetic acidHMDB
beta-GuanidinoacetateHMDB
beta-Guanidinoacetic acidHMDB
BetacyamineHMDB
BetasyamineHMDB
GuanidineacetateHMDB
Guanidineacetic acidHMDB
GuanidylacetateHMDB
Guanidylacetic acidHMDB
Guanyl glycineHMDB
N-Amidino-glycineHMDB
[(Aminoiminomethyl)amino]-acetateHMDB
[(Aminoiminomethyl)amino]-acetic acidHMDB
Glycocyamine, 2-(14)C-labeledHMDB
Glycocyamine, ion (1-)HMDB
Glycocyamine monohydrochlorideHMDB
Molecular FormulaC3H7N3O2
Average Mass117.1066
Monoisotopic Mass117.053826483
IUPAC Name2-carbamimidamidoacetic acid
Traditional Nameglycocyamine
CAS Registry NumberNot Available
SMILES
NC(=N)NCC(O)=O
InChI Identifier
InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)
InChI KeyBPMFZUMJYQTVII-UHFFFAOYSA-N