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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 00:52:45 UTC
Update Date2019-07-25 18:12:31 UTC
HMDB IDHMDB0003584
Secondary Accession Numbers
  • HMDB03584
Metabolite Identification
Common NameTaurocyamine
DescriptionTaurocyamine is a guanidino-taurine analogue derived from taurine. It is an intermediate of taurine and hypotaurine metabolism. The concentration of taurocyamine present in the human urine and serum could be as low as 8-78 pmol/ml. (PMID: 6520173 ) Plasma levels of taurocyamine are significantly increased in patients with chronic renal failure with or without hemodialysis. (PMID: 10516995 ). Taurocyamine is an endogenous alkaline "shifter". It effectively reduces the extent of brain intracellular lactic acidosis brought about by anoxic insult. A pH alkaline shift may protect the brain against the deleterious effects of lactic acidosis. (PMID: 8241459 ). Taurocyamine is an inhibitor of taurine transport and a glycine receptor antagonist in the brain (PMID: 12411417 ).
Structure
Data?1563860750
Synonyms
ValueSource
2-{[amino(imino)methyl]amino}ethanesulfonic acidChEBI
Guanidinoethane sulfonic acidChEBI
N-(Aminoiminomethyl) taurineChEBI
2-{[amino(imino)methyl]amino}ethanesulfonateGenerator
2-{[amino(imino)methyl]amino}ethanesulphonateGenerator
2-{[amino(imino)methyl]amino}ethanesulphonic acidGenerator
Guanidinoethane sulfonateGenerator
Guanidinoethane sulphonateGenerator
Guanidinoethane sulphonic acidGenerator
2-{Carbamimidamido}ethanesulfonateHMDB
2-{Carbamimidamido}ethanesulfonic acidHMDB
GuanidinoethanesulfonateHMDB
Guanidinoethanesulfonic acidHMDB
Guanidinoethyl sulfonateHMDB
Guanodinoethane sulfonateHMDB
Chemical FormulaC3H9N3O3S
Average Molecular Weight167.187
Monoisotopic Molecular Weight167.036461859
IUPAC Name2-[(diaminomethylidene)amino]ethane-1-sulfonic acid
Traditional Name2-[(diaminomethylidene)amino]ethanesulfonic acid
CAS Registry Number543-18-0
SMILES
NC(N)=NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C3H9N3O3S/c4-3(5)6-1-2-10(7,8)9/h1-2H2,(H4,4,5,6)(H,7,8,9)
InChI KeyJKLRIMRKZBSSED-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Guanidine
  • Carboximidamide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility39 mg/mL at 21 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.2 g/LALOGPS
logP-2.3ALOGPS
logP-2.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)11.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.77 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.03 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-5d0ff50ed9e292bc5761JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-d81934294777501815ceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0rr9-6900000000-b75d6cbc0d63f52cdcf6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-5c6e66d0f7839693913aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4900000000-4f6a8534ca438c883a3bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-6900000000-f233f7d655f669f23b46JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6712fd95b9d7a75c12d6JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.33 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.41 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified<0.300 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.56 uMAdult (>18 years old)MaleUremia details
BloodDetected and Quantified1.31 uMAdult (>18 years old)FemaleArteriosclerosis details
Associated Disorders and Diseases
Disease References
Uremia
  1. Kai M, Miyazaki T, Ohkura Y: High-performance liquid chromatographic measurement of guanidino compounds of clinical importance in human urine and serum by pre-column fluorescence derivatization using benzoin. J Chromatogr. 1984 Nov 28;311(2):257-66. [PubMed:6520173 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023202
KNApSAcK IDNot Available
Chemspider ID61635
KEGG Compound IDC01959
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6962
PubChem Compound68340
PDB IDNot Available
ChEBI ID17228
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kai M, Miyazaki T, Ohkura Y: High-performance liquid chromatographic measurement of guanidino compounds of clinical importance in human urine and serum by pre-column fluorescence derivatization using benzoin. J Chromatogr. 1984 Nov 28;311(2):257-66. [PubMed:6520173 ]
  2. Tanaka A, Takahashi Y, Mizokuchi M, Shimada N, Koide H: Plasma, urinary, and erythrocyte concentrations of guanidino compounds in patients with chronic renal failure. Ren Fail. 1999 Sep;21(5):499-514. [PubMed:10516995 ]
  3. Nakada T, Kwee IL: Guanidinoethane sulfate: brain pH alkaline shifter. Neuroreport. 1993 Aug;4(8):1035-8. [PubMed:8241459 ]
  4. Sergeeva OA, Chepkova AN, Haas HL: Guanidinoethyl sulphonate is a glycine receptor antagonist in striatum. Br J Pharmacol. 2002 Nov;137(6):855-60. [PubMed:12411417 ]