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Identification
YMDB IDYMDB00586
Name4-guanidinobutanamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-guanidinobutanamide, also known as tiformin, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. 4-guanidinobutanamide is a very strong basic compound (based on its pKa). 4-guanidinobutanamide exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • 4-Guanidinobutanamide
  • 4-Guanidinobutyramide
  • 4-guanidobutanamide
  • Tiformin
  • Tyformin
  • gamma-Guanidinobutyramide
CAS numberNot Available
WeightAverage: 144.175
Monoisotopic: 144.101111026
InChI KeyYHVFECVVGNXFKO-UHFFFAOYSA-N
InChIInChI=1S/C5H12N4O/c6-4(10)2-1-3-9-5(7)8/h1-3H2,(H2,6,10)(H4,7,8,9)
IUPAC Name4-carbamimidamidobutanamide
Traditional IUPAC Nametiformin
Chemical FormulaC5H12N4O
SMILESNC(=O)CCCNC(N)=N
Chemical Taxonomy
Description belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Guanidine
  • Carboximidamide
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.8 g/LALOGPS
logP-2.4ALOGPS
logP-1.8ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)16.55ChemAxon
pKa (Strongest Basic)12.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area104.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.99 m³·mol⁻¹ChemAxon
Polarizability14.92 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
water + 4-guanidinobutanamide4-guanidinobutanoic acid + Ammonium
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-ae2727d9f39955b4b64bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-68cf6250392b00e8aeceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-9700000000-bc4346c980b745fde210JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-7da32aa7407f832a5c11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-3900000000-84c726f7fa1000af1d50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-9500000000-999e630f0351c962c210JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-67d6b405df4e6e5075f7JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18062
HMDB IDNot Available
Pubchem Compound ID25243936
Kegg IDC03078
ChemSpider ID120
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Furnishes a means for formation of correctly charged Gln-tRNA(Gln) through the transamidation of misacylated Glu- tRNA(Gln) in the mitochondria. The reaction takes place in the presence of glutamine and ATP through an activated gamma-phospho- Glu-tRNA(Gln). Required for HMG2-induced ER-remodeling
Gene Name:
HER2
Uniprot ID:
Q03557
Molecular weight:
50918.0
Reactions
ATP + L-glutamyl-tRNA(Gln) + L-glutamine → ADP + phosphate + L-glutaminyl-tRNA(Gln) + L-glutamate.