Record Information
Version2.0
Creation Date2012-08-15 08:51:29 -0600
Update Date2015-06-03 17:21:59 -0600
Secondary Accession Numbers
  • ECMDB21641
Identification
Name:(R)-Methylmalonyl-CoA
Description:(R)-methylmalonyl-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.
Structure
Thumb
Synonyms:
  • (R)-2-methyl-3-oxopropanoyl-coa
  • (R)-2-methyl-3-oxopropionyl-coa
  • (R)-3-oxo-2-methylpropanoyl-coa
  • (R)-Methylmalonyl-CoA
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2R)-2-methyl-3-oxopropanoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2R)-2-methyl-3-oxopropanoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2R)-2-methyl-3-oxopropanoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2R)-2-methyl-3-oxopropanoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
  • L-MeMal-CoA
  • L-Methylmalonyl-CoA
  • METHYLMALONYL-COENZYME A
Chemical Formula:C25H40N7O19P3S
Weight:Average: 867.607
Monoisotopic: 867.131252359
InChI Key:MZFOKIKEPGUZEN-AGCMQPJKSA-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-/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-3-({2-[(3-{[(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)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid
Traditional IUPAC Name:(2R)-3-({2-[(3-{[(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]-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid
SMILES:[H][C@@](C)(C(O)=O)C(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)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
DescriptionThis compound belongs to the class of chemical entities known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentAcyl CoAs
Alternative Parents
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
  • Fatty amide
  • Monosaccharide
  • Pyrimidine
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Phosphoric acid ester
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carbothioic s-ester
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Sulfenyl compound
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.49 g/LALOGPS
logP-0.4ALOGPS
logP-3.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area407.91 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity184.17 m³·mol⁻¹ChemAxon
Polarizability76.01 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Glyoxylate and dicarboxylate metabolism ec00630
  • Metabolic pathways eco01100
  • Microbial metabolism in diverse environments ec01120
  • Propanoate metabolism ec00640
  • Reductive carboxylate cycle (CO2 fixation) ec00720
  • Valine, leucine and isoleucine degradation ec00280
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00l2-9811041650-6ff1106e71f7373df82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4911110010-0041cbe45f5267a47176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-da5c7610b3b97c5fb82fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3931000120-503dfdefbc3bdbb5e1bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-1911000000-cd0632f31aad1955e31eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3910000000-6b360fd99bac9c77be27View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15465
HMDB IDNot Available
Pubchem Compound ID439439
Kegg IDC01213
ChemSpider ID388548
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoMCA

Enzymes

General function:
Involved in isomerase activity
Specific function:
Specific function unknown
Gene Name:
sbm
Uniprot ID:
P27253
Molecular weight:
77871
Reactions
(R)-methylmalonyl-CoA = succinyl-CoA.