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Record Information
Version	2.0
Creation Date	2012-05-31 13:45:26 -0600
Update Date	2015-06-03 15:53:44 -0600
Secondary Accession Numbers	ECMDB01113
Identification
Name:	Isovaleryl-CoA
Description	Isovaleryl-CoA is a member of the chemical class known as Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond. Isovaleryl-coenzyme A is an intermediate in branched-chain amino acids metabolism. (WikiPedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8ead6928> Close
Synonyms:	3-Methylbutanoyl-CoA 3-Methylbutanoyl-Coenzyme A 3-Methylbutyryl-CoA 3-Methylbutyryl-Coenzyme A Iso-valeryl-CoA Isovaleryl CoA Isovaleryl coenzyme A Isovaleryl-coa Isovaleryl-Coenzyme A S-(3-Methylbutanoate S-(3-Methylbutanoate) coenzyme A S-(3-Methylbutanoic acid S-(3-Methylbutanoic acid) coenzyme A S-isovalerate CoA S-isovalerate Coenzyme A S-Isovaleric acid CoA S-Isovaleric acid coenzyme A
Chemical Formula:	C26H44N7O17P3S
Weight:	Average: 851.651 Monoisotopic: 851.172723243
InChI Key:	UYVZIWWBJMYRCD-ZMHDXICWSA-N
InChI:	InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1
CAS number:	6244-91-3
IUPAC Name:	(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
Traditional IUPAC Name:	(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid
SMILES:	[H][C@](O)(C(O)=NCCC(O)=NCCSC(=O)CC(C)C)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
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 Pentose phosphates Ribonucleoside 3'-phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates N-substituted imidazoles N-acyl amines Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Thioesters Carbothioic S-esters Oxacyclic compounds Azacyclic compounds Sulfenyl compounds Carbonyl compounds Hydrocarbon derivatives Primary amines Organopnictogen compounds Organic oxides
Substituents	Coenzyme a or derivatives Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Ribonucleoside 3'-phosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Pentose monosaccharide Imidazopyrimidine Purine Monoalkyl phosphate Aminopyrimidine Imidolactam N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Monosaccharide Pyrimidine Alkyl phosphate Fatty amide Phosphoric acid ester Tetrahydrofuran Imidazole Azole Heteroaromatic compound Carbothioic s-ester Secondary alcohol Thiocarboxylic acid ester Carboxamide group Secondary carboxylic acid amide Amino acid or derivatives Sulfenyl compound Thiocarboxylic acid or derivatives Organoheterocyclic compound Azacycle Oxacycle Carboxylic acid derivative Organosulfur compound Organic oxygen compound Hydrocarbon derivative Carbonyl group Organic nitrogen compound Primary amine Organopnictogen compound Organic oxide Organooxygen compound Organonitrogen compound Alcohol Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	methylbutanoyl-CoA (CHEBI:15487 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.7 g/L ALOGPS logP -0.27 ALOGPS logP -4.2 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon pKa (Strongest Basic) 6.48 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 370.61 Ų ChemAxon Rotatable Bond Count 22 ChemAxon Refractivity 187.03 m³·mol⁻¹ ChemAxon Polarizability 77.01 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:	Isovaleryl-CoA + ETF-Oxidized 3-Methylcrotonyl-CoA + ETF-Reduced
SMPDB Pathways:	Not Available
KEGG Pathways:	Valine, leucine and isoleucine degradation ec00280
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0019-1931000110-6e3304ddeec458db8be7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01p9-1921000000-845de549ae7b1f22043e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01p9-2910000000-29adb979741d1997fa5b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-8930042460-024bd1d6086dda709313 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-4910010000-a35d045727f719b447d4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-591d51d8eae3a2ce93c8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0udi-0000000190-4b16d8d4cc222eda0259 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0911000680-73061d5c94e047b37bab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-0129000000-ec67a7152f37ad83b9b8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0000000090-c7bb34373c79017b3e8d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-9200102240-ba323ed0ad94f6033a94 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0gds-5002310910-6680dbb92fa184e85ac1 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
References
References:	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 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 15487 HMDB ID HMDB01113 Pubchem Compound ID 165435 Kegg ID C02939 ChemSpider ID 145017 Wikipedia Isovaleryl-coenzyme A BioCyc ID ISOVALERYL-COA EcoCyc ID ISOVALERYL-COA