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Record Information
Version	2.0
Creation Date	2012-10-10 12:20:05 -0600
Update Date	2015-06-03 17:26:04 -0600
Secondary Accession Numbers	ECMDB23166
Identification
Name:	malonyl-CoA methyl ester
Description	Malonyl-CoA methyl ester is an intermediate in biotin synthesis. It a substrate for the enzyme Malonyl-CoA O-methyltransferase BioC which onverts the free carboxyl group of a malonyl-thioester to its methyl ester by transfer of a methyl group from S-adenosyl-L-methionine (SAM). It allows to synthesize pimeloyl-ACP via the fatty acid synthetic pathway. E.coli employs a methylation and demethylation strategy to allow elongation of a temporarily disguised malonate moiety to a pimelate moiety by the fatty acid synthetic enzymes.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa8da1ddc> Close
Synonyms:	Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-3-oxopropanoate Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-3-oxopropanoic acid Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-3-oxopropanoate Methyl 3-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-3-oxopropanoic acid
Chemical Formula:	C25H40N7O19P3S
Weight:	Average: 867.607 Monoisotopic: 867.131252359
InChI Key:	CHQAJZULNPRMEN-ITIYDSSPSA-N
InChI:	InChI=1S/C25H40N7O19P3S/c1-25(2,20(37)23(38)28-5-4-14(33)27-6-7-55-16(35)8-15(34)46-3)10-48-54(44,45)51-53(42,43)47-9-13-19(50-52(39,40)41)18(36)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,36-37H,4-10H2,1-3H3,(H,27,33)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,18-,19-,20+,24-/m1/s1
CAS number:	Not Available
IUPAC Name:	{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:	[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
SMILES:	COC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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 Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates 1,3-dicarbonyl compounds Imidolactams N-acyl amines N-substituted imidazoles Methyl esters Heteroaromatic compounds Tetrahydrofurans Thioesters Secondary alcohols Secondary carboxylic acid amides Carbothioic S-esters Oxacyclic compounds Monocarboxylic acids and derivatives Sulfenyl compounds Azacyclic compounds Primary amines Hydrocarbon derivatives Organic oxides Organopnictogen compounds
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 Aminopyrimidine Monoalkyl phosphate Organic phosphoric acid derivative N-substituted imidazole N-acyl-amine Phosphoric acid ester Monosaccharide Alkyl phosphate Imidolactam Pyrimidine 1,3-dicarbonyl compound Fatty amide Imidazole Azole Heteroaromatic compound Tetrahydrofuran Methyl ester Carbothioic s-ester Thiocarboxylic acid ester Secondary carboxylic acid amide Secondary alcohol Carboxamide group Carboxylic acid ester Amino acid or derivatives Thiocarboxylic acid or derivatives Sulfenyl compound Carboxylic acid derivative Organoheterocyclic compound Azacycle Oxacycle Monocarboxylic acid or derivatives Organic oxygen compound Amine Organonitrogen compound Carbonyl group Organic nitrogen compound Organosulfur compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organooxygen compound Primary amine Alcohol Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.96 g/L ALOGPS logP -0.48 ALOGPS logP -6.9 ChemAxon logS -2.3 ALOGPS pKa (Strongest Acidic) 0.83 ChemAxon pKa (Strongest Basic) 4.95 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 18 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 389.93 Ų ChemAxon Rotatable Bond Count 23 ChemAxon Refractivity 183.32 m³·mol⁻¹ ChemAxon Polarizability 74.61 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:	S-adenosyl-L-methionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
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-1911000130-7ec4913dc885ca0c311c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0912000000-27289dd346d4bf2fa94c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-2911000000-d9ea2c85350a03c21b68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00o0-9821140460-6cd71ffedc1f6bf135fb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-003r-5910010010-ec3af4a8c64ab1635995 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-6900100000-7ce4f36975b302bc9c95 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:	Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
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 46926156 Kegg ID C19673 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes