You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:41:22 UTC
Update Date2016-07-20 21:03:10 UTC
LmdbLMDB00054
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanidoacetic 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 is a very strong basic compound (based on its pKa). Guanidoacetic acid exists in all living organisms, ranging from bacteria to humans. Within humans, guanidoacetic acid participates in a number of enzymatic reactions. In particular, guanidoacetic acid and orotidylic acid can be biosynthesized from glycine and L-arginine; which is mediated by the enzyme glycine amidinotransferase, mitochondrial. In addition, guanidoacetic acid and S-adenosylhomocysteine can be converted into S-adenosylmethionine and creatine through its interaction with the enzyme guanidinoacetate N-methyltransferase. In humans, guanidoacetic acid is involved in glycine and serine metabolism. The N-amidino derivative of glycine. Outside of the human body, Guanidoacetic acid has been detected, but not quantified in, apples and loquats. This could make guanidoacetic acid a potential biomarker for the consumption of these foods. Guanidoacetic acid is a potentially toxic compound.
Structure
Thumb
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 Molecular Weight117.1066
Monoisotopic Molecular Weight117.053826483
IUPAC Name2-carbamimidamidoacetic acid
Traditional Nameglycocyamine
CAS Registry Number352-97-6
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
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0901000000-4a89fe463d29379e6339Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0911000000-542baca9dcca73225bf0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0911200000-bb7ea068f193f39c283bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0901000000-4a89fe463d29379e6339Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0911000000-542baca9dcca73225bf0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0911200000-bb7ea068f193f39c283bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-c703c631a81e400681bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9700000000-1dae820000c4f9ec1662Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-7900000000-4777d20e1ab29262427eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-9000000000-a1b5501bf0f7a9b0489dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-b61a48cf749b57a2c77eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0gk9-7900000000-5ba298286886c1fabdf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9100000000-a5b77a913821d637210fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-9100000000-a5b77a913821d637210fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gk9-7900000000-5ba298286886c1fabdf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-6900000000-4d655a894c702bdfdb59Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-23d5c2795ed49f043127Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-ae360cd8919c8fbce3eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-93406e2cdb79770abc7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-c6bd00733ea6fa3f6e5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-2667e0007de6a723415eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0100-9400000000-c5561d5ccaf260c048ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0g29-9400000000-421d076c4b6868ca69faSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-53db4bf2729a2990a938Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-2cad7322e574eb992175Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01di-9800000000-967331a78fe4a7917408Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-7b281fae734baaa2695dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-1b831140a3071dd98e0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-b27aea734be08f5d2ddcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-dea2f28faa5430d7e56fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9500000000-1ba345c7064e9cb70f9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-6864d4355d3462fbc69fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c36299ab8746bbf67a5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB02751
HMDB IDHMDB0000128
FooDB IDFDB005417
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1594816
BioCyc IDGUANIDOACETIC_ACID
METLIN ID5163
PDB IDNot Available
Wikipedia LinkGlycocyamine
Chemspider ID743
ChEBI ID16344
PubChem Compound ID763
Kegg Compound IDC00581
YMDB IDNot Available
ECMDB IDM2MDB005216
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available