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Record Information
Version	2.0
Creation Date	2015-09-08 17:48:53 -0600
Update Date	2015-09-08 17:48:53 -0600
Secondary Accession Numbers	ECMDB24063
Identification
Name:	Methylmalonyl-CoA
Description
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xad442f70> Close
Synonyms:	Value Source (R)-Methylmalonyl-CoA HMDB (R)-Methylmalonyl-coenzyme A HMDB (S)-2-Methyl-3-oxopropanoyl-CoA HMDB (S)-Methyl-malonyl-CoA HMDB (S)-Methyl-malonyl-coenzyme A HMDB CH3-Malonyl-CoA HMDB CH3-Malonyl-coenzyme A HMDB D-Methylmalonyl-CoA HMDB D-Methylmalonyl-coenzyme A HMDB L-Methylmalonyl-CoA HMDB L-Methylmalonyl-coenzyme A HMDB Methyl-malonyl-coenzyme A HMDB
Chemical Formula:	C25H40N7O19P3S
Weight:	Average: 867.607 Monoisotopic: 867.131252359
InChI Key:	MZFOKIKEPGUZEN-PNEPRAIJSA-N
InChI:	InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13+,16+,17+,18?,22+/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S)-3-{[2-(3-{3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid
Traditional IUPAC Name:	(2S)-3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid
SMILES:	C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
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 Imidolactams N-substituted imidazoles N-acyl amines 1,3-dicarbonyl compounds Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Secondary carboxylic acid amides Thioesters Carbothioic S-esters Amino acids Carboxylic acids Oxacyclic compounds Sulfenyl compounds Azacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Primary amines Hydrocarbon derivatives 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 Alkyl phosphate 1,3-dicarbonyl compound Imidolactam N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Monosaccharide Pyrimidine Fatty amide Phosphoric acid ester Tetrahydrofuran Imidazole Heteroaromatic compound Azole Thiocarboxylic acid ester Carbothioic s-ester Secondary alcohol Amino acid Carboxamide group Amino acid or derivatives Secondary carboxylic acid amide Organoheterocyclic compound Sulfenyl compound Thiocarboxylic acid or derivatives Azacycle Oxacycle Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Organic oxygen compound Primary amine Hydrocarbon derivative Carbonyl group Organosulfur compound Organopnictogen compound Organic oxide Organooxygen compound Organonitrogen compound Organic nitrogen compound Alcohol Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.57 g/L ALOGPS logP -0.6 ALOGPS logP -6.5 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon pKa (Strongest Basic) 4.97 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 400.93 Ų ChemAxon Rotatable Bond Count 22 ChemAxon Refractivity 183.13 m³·mol⁻¹ ChemAxon Polarizability 75.35 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:	Succinyl-CoA + Succinyl-CoA > Methylmalonyl-CoA Methylmalonyl-CoA + Hydrogen ion > Carbon dioxide + Propionyl-CoA + Propionyl-CoA
SMPDB Pathways:	Propanoate metabolism PW000940 threonine biosynthesis PW000817
KEGG Pathways:	Propanoate metabolism ec00640
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 splash10-000i-4911000020-3f5d871d28d1f2657e02 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-1913000000-eb05e99fd73a630e7c4a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-3911000000-ec1f0018f511db865738 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-017j-9811140550-4b48b6e3d5690659e256 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-4911110010-d9e5414e595f184f73ca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-464114c146993e32adb3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-0000000490-c603c70c007f70ef33b6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9100001110-674e7f26ced429f76abf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0fia-6002504900-00628ec73e3d0c21b3b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-0000000190-d1ac902744892ad8fd49 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900002540-5a0ea7d9050df0a16eac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-1159000000-73eadba5e764ea21f78b 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15466 HMDB ID HMDB0001269 Pubchem Compound ID 439291 Kegg ID C00683 ChemSpider ID 388424 Wikipedia ID Methylmalonyl-CoA BioCyc ID Not Available

Enzymes