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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 is a metabolite in the Urea cycle and metabolism of amino groups, and in the metabolic pathways of several amino acids. This includes glycine, serine, threonine, arginine and proline metabolism. Guanidinoacetic acid is also a precursor of creatine, an essential substrate for muscle energy metabolism.
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0901000000-4a89fe463d29379e6339View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0911000000-542baca9dcca73225bf0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0911200000-bb7ea068f193f39c283bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0901000000-4a89fe463d29379e6339View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0911000000-542baca9dcca73225bf0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-0911200000-bb7ea068f193f39c283bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-c703c631a81e400681bdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9700000000-1dae820000c4f9ec1662View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-7900000000-4777d20e1ab29262427eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-9000000000-a1b5501bf0f7a9b0489dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-b61a48cf749b57a2c77eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0gk9-7900000000-5ba298286886c1fabdf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9100000000-a5b77a913821d637210fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-9100000000-a5b77a913821d637210fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gk9-7900000000-5ba298286886c1fabdf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-6900000000-4d655a894c702bdfdb59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-1b831140a3071dd98e0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-b27aea734be08f5d2ddcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-dea2f28faa5430d7e56fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9500000000-1ba345c7064e9cb70f9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-6864d4355d3462fbc69fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c36299ab8746bbf67a5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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 IDFDB021898
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