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Showing NP-Card for Guanidinoacetic Acid (NP0331791)

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Record Information
Version2.0
Created at2023-09-05 20:05:56 UTC
Updated at2024-09-03 04:16:57 UTC
NP-MRD IDNP0331791
Natural Product DOIhttps://doi.org/10.57994/0867
Secondary Accession NumbersNone
Natural Product Identification
Common NameGuanidinoacetic Acid
DescriptionGuanidoacetic acid, also known as guanidinoacetate or N-amidinoglycine, 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. Guanidoacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, guanidoacetic acid is involved in the glycine and serine metabolism pathway. Guanidoacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Guanidinoacetic Acid was first documented in 1995 (PMID: 8547310). Based on a literature review a significant number of articles have been published on Guanidoacetic acid (PMID: 8651275) (PMID: 16855203) (PMID: 12701824) (PMID: 34498202) (PMID: 33664666) (PMID: 32936572).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331791 (Guanidinoacetic Acid)


  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
Download

3D MOL for NP0331791 (Guanidinoacetic Acid)

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
Download

3D SDF for NP0331791 (Guanidinoacetic Acid)


  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>
NP0331791

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0331791 (Guanidinoacetic Acid)

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
Download

PDB for NP0331791 (Guanidinoacetic Acid)

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 NP0331791 (Guanidinoacetic Acid)

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 NP0331791 (Guanidinoacetic Acid)

NC(=N)NCC(O)=O
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INCHI for NP0331791 (Guanidinoacetic Acid)

InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)
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View in JSmol
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
Chemical FormulaC3H7N3O2
Average Mass117.1066 Da
Monoisotopic Mass117.05383 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Guanidine
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)12.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.72 m³·mol⁻¹ChemAxon
Polarizability10.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000128
DrugBank IDDB02751
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005417
KNApSAcK IDC00051746
Chemspider ID743
KEGG Compound IDC00581
BioCyc IDGUANIDOACETIC_ACID
BiGG ID1594816
Wikipedia LinkGlycocyamine
METLIN ID5163
PubChem Compound763
PDB IDNot Available
ChEBI ID16344
Good Scents IDrw1248881
References
General References
  1. Isbrandt D, von Figura K: Cloning and sequence analysis of human guanidinoacetate N-methyltransferase cDNA. Biochim Biophys Acta. 1995 Dec 27;1264(3):265-7. [PubMed:8547310 ]
  2. Stockler S, Isbrandt D, Hanefeld F, Schmidt B, von Figura K: Guanidinoacetate methyltransferase deficiency: the first inborn error of creatine metabolism in man. Am J Hum Genet. 1996 May;58(5):914-22. [PubMed:8651275 ]
  3. Mercimek-Mahmutoglu S, Stoeckler-Ipsiroglu S, Adami A, Appleton R, Araujo HC, Duran M, Ensenauer R, Fernandez-Alvarez E, Garcia P, Grolik C, Item CB, Leuzzi V, Marquardt I, Muhl A, Saelke-Kellermann RA, Salomons GS, Schulze A, Surtees R, van der Knaap MS, Vasconcelos R, Verhoeven NM, Vilarinho L, Wilichowski E, Jakobs C: GAMT deficiency: features, treatment, and outcome in an inborn error of creatine synthesis. Neurology. 2006 Aug 8;67(3):480-4. Epub 2006 Jul 19. [PubMed:16855203 ]
  4. Schulze A: Creatine deficiency syndromes. Mol Cell Biochem. 2003 Feb;244(1-2):143-50. [PubMed:12701824 ]
  5. Yang H, Zhang P, Xie M, Luo J, Zhang J, Zhang G, Wang Y, Lin H, Ji Z: Parallel Metabolomic Profiling of Cerebrospinal Fluid, Plasma, and Spinal Cord to Identify Biomarkers for Spinal Cord Injury. J Mol Neurosci. 2022 Jan;72(1):126-135. doi: 10.1007/s12031-021-01903-w. Epub 2021 Sep 9. [PubMed:34498202 ]
  6. Aleidi SM, Dahabiyeh LA, Gu X, Al Dubayee M, Alshahrani A, Benabdelkamel H, Mujammami M, Li L, Aljada A, Abdel Rahman AM: Obesity Connected Metabolic Changes in Type 2 Diabetic Patients Treated With Metformin. Front Pharmacol. 2021 Feb 16;11:616157. doi: 10.3389/fphar.2020.616157. eCollection 2020. [PubMed:33664666 ]
  7. Pintus R, Bongiovanni T, Corbu S, Francavilla VC, DessI A, Noto A, Corsello G, Finco G, Fanos V, Cesare Marincola F: Sportomics in professional soccer players: metabolomics results during preseason. J Sports Med Phys Fitness. 2021 Feb;61(2):324-330. doi: 10.23736/S0022-4707.20.11200-3. Epub 2020 Sep 16. [PubMed:32936572 ]
  8. Ogunade IM, McCoun M: Average daily gain divergence in beef steers is associated with altered plasma metabolome and whole blood immune-related gene expression. Transl Anim Sci. 2020 May 27;4(3):txaa074. doi: 10.1093/tas/txaa074. eCollection 2020 Jul. [PubMed:32734144 ]
  9. Sasaki C, Hiraishi T, Oku T, Okuma K, Suzumura K, Hashimoto M, Ito H, Aramori I, Hirayama Y: Metabolomic approach to the exploration of biomarkers associated with disease activity in rheumatoid arthritis. PLoS One. 2019 Jul 11;14(7):e0219400. doi: 10.1371/journal.pone.0219400. eCollection 2019. [PubMed:31295280 ]
  10. Kim SY, Kim BK, Gwon MR, Seong SJ, Ohk B, Kang WY, Lee HW, Jung HY, Cho JH, Chung BH, Lee SH, Kim YH, Yoon YR, Kim CD, Cho S: Urinary metabolomic profiling for noninvasive diagnosis of acute T cell-mediated rejection after kidney transplantation. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Jun 15;1118-1119:157-163. doi: 10.1016/j.jchromb.2019.04.047. Epub 2019 Apr 24. [PubMed:31054449 ]
  11. Li JZ, Qu H, Wu J, Zhang F, Jia ZB, Sun JY, Lv B, Kang Y, Jiang SL, Kang K: Metabolic profiles of adipose-derived and bone marrow-derived stromal cells from elderly coronary heart disease patients by capillary liquid chromatography quadrupole time-of-flight mass spectrometry. Int J Mol Med. 2018 Jan;41(1):184-194. doi: 10.3892/ijmm.2017.3198. Epub 2017 Oct 19. [PubMed:29115374 ]
  12. Kiyatake I, Nakamura T, Koide H: Urinary guanidinoacetic acid excretion as an indicator of gentamicin nephrotoxicity in rats. Ren Fail. 2004 Jul;26(4):339-44. doi: 10.1081/jdi-120039812. [PubMed:15462098 ]
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