4-guanidinobutanamide (YMDB00586)

Identification

YMDB ID

YMDB00586

Name

4-guanidinobutanamide

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

4-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

MOL SDF PDB SMILES InChI

Synonyms

4-Guanidinobutanamide
4-Guanidinobutyramide
4-guanidobutanamide
Tiformin
Tyformin
gamma-Guanidinobutyramide

CAS number

Not Available

Weight

Average: 144.175
Monoisotopic: 144.101111026

InChI Key

YHVFECVVGNXFKO-UHFFFAOYSA-N

InChI

InChI=1S/C5H12N4O/c6-4(10)2-1-3-9-5(7)8/h1-3H2,(H2,6,10)(H4,7,8,9)

IUPAC Name

4-carbamimidamidobutanamide

Traditional IUPAC Name

tiformin

Chemical Formula

C₅H₁₂N₄O

SMILES

NC(=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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Guanidine
Carboximidamide
Carboximidic acid derivative
Carboximidic acid
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:18062 )
butanamides (CHEBI:18062 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.8 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.8	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	16.55	ChemAxon
pKa (Strongest Basic)	12.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	104.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.99 m³·mol⁻¹	ChemAxon
Polarizability	14.92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Arginine and proline metabolism

ec00330

SMPDB Reactions

Not Available

KEGG Reactions

water + 4-guanidinobutanamide → 4-guanidinobutanoic acid + Ammonium

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-ae2727d9f39955b4b64b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-68cf6250392b00e8aece	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-9700000000-bc4346c980b745fde210	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-7da32aa7407f832a5c11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6x-3900000000-84c726f7fa1000af1d50	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfu-9500000000-999e630f0351c962c210	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-67d6b405df4e6e5075f7	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	18062
HMDB ID	Not Available
Pubchem Compound ID	25243936
Kegg ID	C03078
ChemSpider ID	120
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Glutamyl-tRNA(Gln) amidotransferase subunit A, mitochondrial

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.

Structure for #<Compound:0xaaa909fc>

Enzymes

Reactions