Showing NP-Card for 4-Guanidinobutanoic acid (NP0001360)

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Record Information
Version2.0
Created at2006-08-12 21:31:07 UTC
Updated at2021-06-29 00:47:49 UTC
NP-MRD IDNP0001360
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001360 (4-Guanidinobutanoic acid)

 
  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
Download

3D MOL for NP0001360 (4-Guanidinobutanoic acid)

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 NP0001360 (4-Guanidinobutanoic acid)

 
  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>
NP0001360

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001360 (4-Guanidinobutanoic acid)

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 NP0001360 (4-Guanidinobutanoic acid)

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 NP0001360 (4-Guanidinobutanoic acid)

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 NP0001360 (4-Guanidinobutanoic acid)

NC(=N)NCCCC(O)=O
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INCHI for NP0001360 (4-Guanidinobutanoic acid)

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
Chemical FormulaC5H11N3O2
Average Mass145.1597 Da
Monoisotopic Mass145.08513 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Straight chain fatty acid
  • Fatty acid
  • Fatty acyl
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP-1.5ALOGPS
logP-2.7ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)12.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.88 m³·mol⁻¹ChemAxon
Polarizability14.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003464
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004103
KNApSAcK IDC00053195
Chemspider ID486
KEGG Compound IDC01035
BioCyc IDCPD-592
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6938
PubChem Compound500
PDB IDNot Available
ChEBI ID15728
Good Scents IDNot Available
References
General References
  1. 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. [PubMed:3433275 ]
  2. 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. [PubMed:3987036 ]
  3. Gatti R, Gioia MG: Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. J Pharm Biomed Anal. 2006 Sep 11;42(1):11-6. Epub 2006 Feb 3. [PubMed:16460903 ]
  4. De Deyn PP, Marescau B, Cuykens JJ, Van Gorp L, Lowenthal A, De Potter WP: Guanidino compounds in serum and cerebrospinal fluid of non-dialyzed patients with renal insufficiency. Clin Chim Acta. 1987 Jul 30;167(1):81-8. [PubMed:3665089 ]