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Record Information
Version	2.0
Creation Date	2012-05-31 14:50:38 -0600
Update Date	2015-06-03 17:20:18 -0600
Secondary Accession Numbers	ECMDB20559
Identification
Name:	gamma-Butyrobetainyl-CoA
Description	Gamma-butyrobetainyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. When gamma-butyrobetainyl-CoA was used as a cosubstrate (CoA donor), the first reaction is the CoA transfer. (PMID 11551212) E. coli protein CaiB, which is a member of the recently identified type-III coenzyme A (CoA) transferase family and catalyzes the transfer of the CoA moiety between gamma-butyrobetaine-CoA and carnitine forming carnityl-CoA and gamma-butyrobetaine. (PMID 15518548)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa60c340> Close
Synonyms:	γ-butyrobetaine-CoA g-Butyrobetaine-CoA g-Butyrobetainyl-CoA Gamma-Butyrobetaine-coa γ-Butyrobetaine-CoA γ-Butyrobetainyl-CoA
Chemical Formula:	C28H50N8O17P3S
Weight:	Average: 895.726 Monoisotopic: 895.22274744
InChI Key:	QAMRRBGWSPTAEJ-UHFFFAOYSA-O
InChI:	InChI=1S/C28H49N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,39-40H,6-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1
CAS number:	Not Available
IUPAC Name:	[4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobutyl]trimethylazanium
Traditional IUPAC Name:	{4-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-4-oxobutyl}trimethylazanium
SMILES:	CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CCC[N+](C)(C)C
Chemical Taxonomy
Description	belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	Acyl CoAs
Alternative Parents	Coenzyme A and derivatives Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Pentose phosphates Glycosylamines Beta amino acids and derivatives Monosaccharide phosphates Organic pyrophosphates 6-aminopurines Monoalkyl phosphates Aminopyrimidines and derivatives Imidolactams N-acyl amines N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Tetraalkylammonium salts Secondary carboxylic acid amides Carbothioic S-esters Thioesters Secondary alcohols Sulfenyl compounds Azacyclic compounds Oxacyclic compounds Primary amines Hydrocarbon derivatives Carbonyl compounds Organic oxides Organic salts Organopnictogen compounds Organic cations
Substituents	Coenzyme a or derivatives Purine ribonucleoside diphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside 3',5'-bisphosphate Ribonucleoside 3'-phosphate Pentose-5-phosphate Pentose phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound Organic pyrophosphate Pentose monosaccharide Monosaccharide phosphate 6-aminopurine Imidazopyrimidine Purine Aminopyrimidine Monoalkyl phosphate Monosaccharide N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Fatty amide Imidolactam Phosphoric acid ester Alkyl phosphate Pyrimidine Tetrahydrofuran Quaternary ammonium salt Heteroaromatic compound Imidazole Azole Tetraalkylammonium salt Thiocarboxylic acid ester Secondary carboxylic acid amide Secondary alcohol Carboxamide group Carbothioic s-ester Amino acid or derivatives Carboxylic acid derivative Sulfenyl compound Organoheterocyclic compound Oxacycle Thiocarboxylic acid or derivatives Azacycle Organic nitrogen compound Alcohol Organonitrogen compound Organooxygen compound Organosulfur compound Primary amine Organic salt Carbonyl group Hydrocarbon derivative Organic oxide Organopnictogen compound Organic oxygen compound Amine Organic cation Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.2 g/L ALOGPS logP -1.4 ALOGPS logP -7.9 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 0.83 ChemAxon pKa (Strongest Basic) 4.79 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 370.61 Ų ChemAxon Rotatable Bond Count 24 ChemAxon Refractivity 212.05 m³·mol⁻¹ ChemAxon Polarizability 84.92 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 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:	gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine gamma-Butyrobetainyl-CoA + an oxidized electron acceptor <> Crotonobetainyl-CoA + a reduced electron acceptor Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine Crotonobetainyl-CoA + reduced electron acceptor > gamma-Butyrobetainyl-CoA + oxidized electron acceptor gamma-Butyrobetainyl-CoA + L-Carnitine > D-Carnitinyl-CoA + gamma-Butyrobetaine
SMPDB Pathways:	L-carnitine degradation I PW002037
KEGG Pathways:	Not Available
EcoCyc Pathways:	carnitine degradation I CARNMET-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-1923030230-d48b9d23973c17c674fa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0932000000-4f0839c2e3784a9a888a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1911000000-eb800903e22fa47dc186 View in MoNA 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
References
References:	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 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 726 Kegg ID Not Available ChemSpider ID 706 Wikipedia ID Not Available BioCyc ID GAMMA-BUTYROBETAINYL-COA EcoCyc ID GAMMA-BUTYROBETAINYL-COA

Enzymes