Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 13:52:33 -0600
Update Date	2015-09-13 12:56:11 -0600
Secondary Accession Numbers	ECMDB01432
Identification
Name:	Agmatine
Description	Agmatine (also known as (4-aminobutyl)guanidine) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. (Wikipedia) In E. coli arginine metabolism, agmatine is produced from arginine in a reaction catalyzed by arginine decarboxylase (4.1.1.19). Another enzyme, agmatinase (EC 3.5.3.11), can then convert agmatine to putrescine, which is a polyamine that can be further converted to other products such as spermidine. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xad63ce5c> Close
Synonyms:	(4-aminobutyl)-Guanidine (4-Aminobutyl)guanidine 1-(4-Aminobutyl)guanidine 1-Amino-4-guanidinobutane 1-Amino-4-guanidobutane 4-Guanidino-1-butanamine Agmatine Argmatine N-(4-Aminobutyl)guanidine N-(Aminoiminomethyl)-1,4-Butanediamine N-4-Aminobutylguanidine
Chemical Formula:	C5H14N4
Weight:	Average: 130.1915 Monoisotopic: 130.121846468
InChI Key:	QYPPJABKJHAVHS-UHFFFAOYSA-N
InChI:	InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)
CAS number:	306-60-5
IUPAC Name:	N-(4-aminobutyl)guanidine
Traditional IUPAC Name:	agmatine
SMILES:	NCCCCNC(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	Carboximidamides Organopnictogen compounds Monoalkylamines Imines Hydrocarbon derivatives
Substituents	Guanidine Carboximidamide Organopnictogen compound Hydrocarbon derivative Primary amine Primary aliphatic amine Imine Amine Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	guanidines (CHEBI:17431 ) primary amino compound (CHEBI:17431 ) Amines (C00179 )
Physical Properties
State:	Solid
Charge:	2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.61 g/L ALOGPS logP -1 ALOGPS logP -1.2 ChemAxon logS -1.6 ALOGPS pKa (Strongest Basic) 12.61 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 87.92 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 48.09 m³·mol⁻¹ ChemAxon Polarizability 15.01 ų 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
Reactions:	Agmatine + Water <> Putrescine + Urea + Ethylenediamine L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide L-Arginine + Hydrogen ion > Agmatine + Carbon dioxide L-Arginine <> Agmatine + Carbon dioxide Agmatine + Water <> Putrescine + Urea Water + Agmatine > Urea + Putrescine L-Arginine > Agmatine + Carbon dioxide L-Arginine + Hydrogen ion + Carbon dioxide > Agmatine L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide
SMPDB Pathways:	arginine metabolism PW000790
KEGG Pathways:	Arginine and proline metabolism ec00330 Metabolic pathways eco01100
EcoCyc Pathways:	arginine degradation III (arginine decarboxylase/agmatinase pathway) PWY0-823 arginine dependent acid resistance PWY0-1299 putrescine biosynthesis I PWY-40
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 10± 0 uM K12 HB101 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Mid Log Phase Shake flask 37 oC PMID: 8742354 110± 0 uM K12 HB101 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Stationary Phase Shake flask 37 oC PMID: 8742354 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0002-0900000000-a9f6a71ff1ddda580ea9 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-00di-1910000000-4c97cf5e84d752009d1a View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-00di-1910000000-de398de0f062b85c083c View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00di-1910000000-de398de0f062b85c083c View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-00di-1910000000-de398de0f062b85c083c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-008c-9000000000-ba695487db67f42d2617 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-00e9-9700000000-dcb266f2466b6490a487 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00di-9000000000-e4747ffbbb1c0aa02f4e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-00di-9000000000-e97e998997ab8bfcedb5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-001i-0900000000-4843789c1dd06e41493d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-00di-9200000000-a6b84c1241179a3739f8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-00di-9000000000-57f390519e8ddbcb80a8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-00di-9000000000-e38858b8c1a4fb2a6b14 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-00di-9000000000-2e6fd942608b84941a7d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-001i-0900000000-075bad34dbbb7544e053 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-00di-9600000000-368edccb095766335b38 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-001i-0900000000-6599222abf093d406584 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-001i-0900000000-4843789c1dd06e41493d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00di-9200000000-a6b84c1241179a3739f8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00di-9000000000-57f390519e8ddbcb80a8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00di-9000000000-e38858b8c1a4fb2a6b14 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00di-9000000000-2e6fd942608b84941a7d View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-001i-0900000000-075bad34dbbb7544e053 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-00di-9600000000-368edccb095766335b38 View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0229-9500000000-1c515d08e5bc52668dc4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03e9-3900000000-21dc8634e0e5c79fc825 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-9300000000-55aa9e9ef7923b67457f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03dl-9000000000-ec5b24cf1199482a883d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002r-9500000000-f8e119f2ba53222591a1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9000000000-c4883e27e32ef6874c13 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-2b9c32eb2684272e86a2 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Atlas D: Molecular and physiological properties of clonidine-displacing substance. Ann N Y Acad Sci. 1995 Jul 12;763:314-24. Pubmed: 7677341 Feng Y, Halaris AE, Piletz JE: Determination of agmatine in brain and plasma using high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 1997 Apr 11;691(2):277-86. Pubmed: 9174263 Halaris A, Piletz JE: Relevance of imidazoline receptors and agmatine to psychiatry: a decade of progress. Ann N Y Acad Sci. 2003 Dec;1009:1-20. Pubmed: 15028565 Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. Pubmed: 8742354 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064 Zhao S, Wang B, Yuan H, Xiao D: Determination of agmatine in biological samples by capillary electrophoresis with optical fiber light-emitting-diode-induced fluorescence detection. J Chromatogr A. 2006 Aug 4;1123(1):138-41. Epub 2006 Jul 3. Pubmed: 16820162
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 17431 HMDB ID HMDB01432 Pubchem Compound ID 199 Kegg ID C00179 ChemSpider ID 194 Wikipedia Agmatine BioCyc ID AGMATHINE EcoCyc ID AGMATHINE Ligand Expo AG2

Enzymes

Transporters