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Showing Compound Guanidino acetic acid (FDB005417)

Record Information
Version1.0
Creation date2010-04-08 22:06:40 UTC
Update date2024-11-29 22:25:37 UTC
Primary IDFDB005417
Secondary Accession Numbers
  • FDB021898
Chemical Information
FooDB NameGuanidino acetic acid
DescriptionGuanidino acetic acid, also known as guanidinoacetate or glycocyamine, belongs to alpha amino acids and derivatives class of compounds. Those 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. Guanidino acetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Guanidino acetic acid can be found in apple and loquat, which makes guanidino acetic acid a potential biomarker for the consumption of these food products. Guanidino acetic acid can be found primarily in most biofluids, including cellular cytoplasm, feces, urine, and cerebrospinal fluid (CSF), as well as in human brain, kidney and liver tissues. In humans, guanidino acetic acid is involved in a couple of metabolic pathways, which include arginine and proline metabolism and glycine and serine metabolism. Guanidino acetic acid is also involved in several metabolic disorders, some of which include dihydropyrimidine dehydrogenase deficiency (DHPD), hyperprolinemia type II, prolinemia type II, and hyperornithinemia-hyperammonemia-homocitrullinuria [hhh-syndrome]. Moreover, guanidino acetic acid is found to be associated with chronic renal failure and schizophrenia. Guanidino acetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
CAS Number352-97-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Predicted Properties
PropertyValueSource
Water Solubility4.19 g/LALOGPS
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
Chemical FormulaC3H7N3O2
IUPAC name2-carbamimidamidoacetic acid
InChI IdentifierInChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)
InChI KeyBPMFZUMJYQTVII-UHFFFAOYSA-N
Isomeric SMILESNC(=N)NCC(O)=O
Average Molecular Weight117.1066
Monoisotopic Molecular Weight117.053826483
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-0901000000-4a89fe463d29379e6339Spectrum
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-0911000000-542baca9dcca73225bf0Spectrum
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-006t-0911200000-bb7ea068f193f39c283bSpectrum
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-0901000000-4a89fe463d29379e6339Spectrum
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-00di-0911000000-542baca9dcca73225bf0Spectrum
GC-MSGuanidino acetic acid, non-derivatized, GC-MS Spectrumsplash10-006t-0911200000-bb7ea068f193f39c283bSpectrum
Predicted GC-MSGuanidino acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-c703c631a81e400681bdSpectrum
Predicted GC-MSGuanidino acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9700000000-1dae820000c4f9ec1662Spectrum
Predicted GC-MSGuanidino acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGuanidino acetic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-7900000000-4777d20e1ab29262427e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-9000000000-a1b5501bf0f7a9b0489d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-b61a48cf749b57a2c77e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0gk9-7900000000-5ba298286886c1fabdf52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9100000000-a5b77a913821d637210f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-9100000000-a5b77a913821d637210f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gk9-7900000000-5ba298286886c1fabdf52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-6900000000-4d655a894c702bdfdb592017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-23d5c2795ed49f0431272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-ae360cd8919c8fbce3ee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-93406e2cdb79770abc7d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-c6bd00733ea6fa3f6e5d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-2667e0007de6a723415e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0100-9400000000-c5561d5ccaf260c048ec2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0g29-9400000000-421d076c4b6868ca69fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-53db4bf2729a2990a9382021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-2cad7322e574eb9921752021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-01di-9800000000-967331a78fe4a79174082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-7b281fae734baaa2695d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-1b831140a3071dd98e0c2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9300000000-b27aea734be08f5d2ddc2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-dea2f28faa5430d7e56f2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-9500000000-1ba345c7064e9cb70f9c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-6864d4355d3462fbc69f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c36299ab8746bbf67a52017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGUANIDINOACETIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of CreatinineSMP0123283 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).