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Showing Compound Guanidinosuccinic acid (FDB023116)

Record Information
Version1.0
Creation date2011-09-21 00:24:55 UTC
Update date2015-10-09 22:32:39 UTC
Primary IDFDB023116
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuanidinosuccinic acid
DescriptionGuanidinosuccinic acid (GSA) is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806) [HMDB]
CAS Number6133-30-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2S)-2-Carbamimidamidobutanedioic acidChEBI
L-N-Amidinoaspartic acidChEBI
N-(Aminoiminomethyl)-L-aspartic acidChEBI
N-Amidino-L-aspartic acidKegg
(2S)-2-CarbamimidamidobutanedioateGenerator
L-N-AmidinoaspartateGenerator
N-(Aminoiminomethyl)-L-aspartateGenerator
N-Amidino-L-aspartateGenerator
GuanidinosuccinateGenerator
N-Carbamimidoyl-L-aspartic acidHMDB
Guanidinosuccinic acid, (DL)-isomerMeSH, HMDB
Guanidinosuccinic acidChEBI
L-N-amidinoaspartic acidhmdb
N-(aminoiminomethyl)-L-aspartic acidhmdb
N-amidino-L-aspartic acidhmdb
N-carbamimidoyl-L-aspartic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.82 g/LALOGPS
logP-1.6ALOGPS
logP-3.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)12.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability15.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9N3O4
IUPAC name(2S)-2-carbamimidamidobutanedioic acid
InChI IdentifierInChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1
InChI KeyVVHOUVWJCQOYGG-REOHCLBHSA-N
Isomeric SMILESNC(=N)N[C@@H](CC(O)=O)C(O)=O
Average Molecular Weight175.1427
Monoisotopic Molecular Weight175.059305791
Classification
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Predicted GC-MSGuanidinosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-9600000000-6898be602fa231388ab5Spectrum
Predicted GC-MSGuanidinosuccinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9282000000-37ec05543d3d8d30ad15Spectrum
Predicted GC-MSGuanidinosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-1900000000-466615ceb5129f0853332012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-e5868bbf32c1407fa0302012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-f34cd801b9c1e714a6fc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9200000000-2cad41f1508b5f26c3a42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0079-9100000000-05168c0ae4e3fdabfb732021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3900000000-df5df4302173fb4e9d292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001r-5900000000-a31472885115c01298852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36781515ea42c79fcca52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-005i-5900000000-37fe8d8d0c84140e147c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ba089dcdaa7d9545ac432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-005i-2900000000-d58d2731ca71e2359e242021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-005i-3900000000-e366d1ed9f73879bd47f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-49e8a9df2b750e4946852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9000000000-948b748bb9ac50e676a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9100000000-ac4c3bddfe7b0a568fff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-e7544c898162e6c51b542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-3900000000-f755abe1d2fcfc810e3f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0079-9200000000-78e26e891d49a63dc6b62021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-766bed5b22ec642474b72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-090r-6900000000-c59abb9d78dd85396ad92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-809ece24ff681a9892302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1900000000-ab305bd5f1306019d2bb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-9500000000-e46a9bb7a8167700416d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-cf381fa0309c6e1df17d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02a9-6900000000-3e4021155970f30bc06c2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID388951
ChEMBL IDNot Available
KEGG Compound IDC03139
Pubchem Compound ID439918
Pubchem Substance IDNot Available
ChEBI ID17072
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03157
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
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
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference