Showing metabocard for 4-guanidinobutanoic acid (MMDBc0033043)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:32:17 UTC
Update Date2024-04-30 19:59:20 UTC
Metabolite IDMMDBc0033043
Metabolite Identification
Common Name4-guanidinobutanoic acid
Description4-Guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-Guanidinobutanoic acid is a normal metabolite present in low concentrations. 4-Guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, 4-Guanidinobutanoic acid has been detected, but not quantified in a few different foods, such as apples, french plantains, and loquats. This could make 4-guanidinobutanoic acid a potential biomarker for the consumption of these foods. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000564aeff72250>

 
  Mrv1652309042000292D          

 10  9  0  0  0  0            999 V2000
   31.2515  -24.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5404  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7875  -24.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0764  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3653  -24.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6124  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9013  -24.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1484  -25.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5404  -26.0357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9013  -23.9442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  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  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  2  0  0  0  0
  7 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000564aeff72250>

HMDB0003464
     RDKit          3D
4-Guanidinobutanoic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.7626   -0.3987   -0.3203 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764    0.1679    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    1.5824    0.0888 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709   -0.6391    0.4090 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2802   -0.2466   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200   -1.1718    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -0.7144   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    0.6255    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    1.3541    1.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512    1.1048   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8287   -1.4170   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    2.0169    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190    2.1707   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.4680    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    0.7824    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -0.3258   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803   -1.2041    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -2.1859   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329   -1.4793   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640   -0.6347   -1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    2.0808   -0.3219 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x0000564aeff72250>

 
  Mrv1652309042000292D          

 10  9  0  0  0  0            999 V2000
   31.2515  -24.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5404  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7875  -24.7808    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0764  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3653  -24.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6124  -25.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9013  -24.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1484  -25.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5404  -26.0357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9013  -23.9442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  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  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  2  0  0  0  0
  7 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033043

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8)

> <INCHI_KEY>
TUHVEAJXIMEOSA-UHFFFAOYSA-N

> <FORMULA>
C5H11N3O2

> <MOLECULAR_WEIGHT>
145.1597

> <EXACT_MASS>
145.085126611

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.705032842824645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(diaminomethylidene)amino]butanoic acid

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-2.654531034416961

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.23994567518324

> <JCHEM_PKA_STRONGEST_BASIC>
12.068589169762964

> <JCHEM_POLAR_SURFACE_AREA>
101.69999999999999

> <JCHEM_REFRACTIVITY>
35.879599999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(diaminomethylidene)amino]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000564aeff72250>

HMDB0003464
     RDKit          3D
4-Guanidinobutanoic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.7626   -0.3987   -0.3203 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764    0.1679    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    1.5824    0.0888 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709   -0.6391    0.4090 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2802   -0.2466   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200   -1.1718    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -0.7144   -0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    0.6255    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    1.3541    1.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512    1.1048   -0.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8287   -1.4170   -0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    2.0169    0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190    2.1707   -0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.4680    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    0.7824    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -0.3258   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803   -1.2041    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -2.1859   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329   -1.4793   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640   -0.6347   -1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519    2.0808   -0.3219 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
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PDB for #<Metabolite:0x0000564aeff72250>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0      58.336 -46.257   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      57.009 -47.038   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      55.603 -46.257   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      54.276 -47.038   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      52.949 -46.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.543 -47.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.216 -46.257   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      48.810 -47.038   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      57.009 -48.600   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      50.216 -44.696   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7                                                            
CONECT    9    2                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x0000564aeff72250>

COMPND    HMDB0003464
HETATM    1  N1  UNL     1       3.763  -0.399  -0.320  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.676   0.168   0.039  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.519   1.582   0.089  1.00  0.00           N  
HETATM    4  N3  UNL     1       1.571  -0.639   0.409  1.00  0.00           N  
HETATM    5  C2  UNL     1       0.280  -0.247  -0.101  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.820  -1.172   0.353  1.00  0.00           C  
HETATM    7  C4  UNL     1      -2.135  -0.714  -0.213  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.554   0.625   0.232  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.961   1.354   1.053  1.00  0.00           O  
HETATM   10  O2  UNL     1      -3.751   1.105  -0.349  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.829  -1.417  -0.340  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.931   2.017   0.815  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.019   2.171  -0.632  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.668  -1.468   1.012  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.008   0.782   0.141  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.325  -0.326  -1.225  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.880  -1.204   1.463  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.538  -2.186  -0.006  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.933  -1.479  -0.068  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.064  -0.635  -1.340  1.00  0.00           H  
HETATM   21  H11 UNL     1      -3.952   2.081  -0.322  1.00  0.00           H  
CONECT    1    2    2   11
CONECT    2    3    4
CONECT    3   12   13
CONECT    4    5   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for #<Metabolite:0x0000564aeff72250>

NC(=N)NCCCC(O)=O
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INCHI for #<Metabolite:0x0000564aeff72250>

InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8)
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Synonyms
ValueSource
4-GuanidinobutanoateChEBI
4-Guanidinobutyric acidChEBI
gamma-GuanidinobutyrateChEBI
gamma-Guanidinobutyric acidChEBI
4-GuanidinobutyrateGenerator
g-GuanidinobutyrateGenerator
g-Guanidinobutyric acidGenerator
Γ-guanidinobutyrateGenerator
Γ-guanidinobutyric acidGenerator
4-(Carbamimidamido)butanoateHMDB
4-(Carbamimidamido)butanoic acidHMDB
gamma-Guanidinobutyrate, monosodium saltHMDB
4-[(Aminoiminomethyl)amino]butanoateHMDB
4-[(Aminoiminomethyl)amino]butanoic acidHMDB
N-(4-Butanoate)guanidineHMDB
N-(4-Butanoic acid)guanidineHMDB
gamma-GuanidinebutyrateHMDB
gamma-Guanidinebutyric acidHMDB
Γ-guanidinebutyrateHMDB
Γ-guanidinebutyric acidHMDB
4-Guanidinobutanoic acidGenerator
Molecular FormulaC5H11N3O2
Average Mass145.1597
Monoisotopic Mass145.085126611
IUPAC Name4-[(diaminomethylidene)amino]butanoic acid
Traditional Name4-[(diaminomethylidene)amino]butanoic acid
CAS Registry Number463-00-3
SMILES
NC(=N)NCCCC(O)=O
InChI Identifier
InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8)
InChI KeyTUHVEAJXIMEOSA-UHFFFAOYSA-N