Human Metabolome Database Version 3.5

Showing metabocard for R-Methylmalonyl-CoA (HMDB02255)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:44 -0600
Update Date 2013-02-08 17:11:38 -0700
HMDB ID HMDB02255
Secondary Accession Numbers None
Metabolite Identification
Common Name R-Methylmalonyl-CoA
Description Methylmalonyl-CoA is an intermediate in the metabolism of Propanoate. It is a substrate for Malonyl-CoA decarboxylase (mitochondrial), Methylmalonyl-CoA mutase (mitochondrial) and Methylmalonyl-CoA epimerase (mitochondrial).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C25H40N7O19P3S
Average Molecular Weight 867.607
Monoisotopic Molecular Weight 867.131252359
IUPAC Name (2R)-3-[(2-{3-[(2R)-3-[({[({[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 (2R)-3-[(2-{3-[(2R)-3-{[({[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
CAS Registry Number 73173-92-9
SMILES C[C@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier 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
InChI Key MZFOKIKEPGUZEN-YLYUOEEYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Carboxamide Group
  • Carboxylic Acid
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside 3',5' Bisphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.57 g/L ALOGPS
LogP -0.60 ALOGPS
LogP -6.5 ChemAxon
LogS -2.39 ALOGPS
pKa (strongest acidic) 0.82 ChemAxon
pKa (strongest basic) 4.97 ChemAxon
Hydrogen Acceptor Count 19 ChemAxon
Hydrogen Donor Count 10 ChemAxon
Polar Surface Area 400.93 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 183.13 ChemAxon
Polarizability 76.4 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -5 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Propanoate Metabolism SMP00016 map00640 Link_out
Threonine and 2-Oxobutanoate Degradation SMP00452 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022930
KNApSAcK ID Not Available
Chemspider ID 17216177 Link_out
KEGG Compound ID C01213 Link_out
BioCyc ID METHYL-MALONYL-COA Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02255 Link_out
Metagene Link HMDB02255 Link_out
METLIN ID 6577 Link_out
PubChem Compound 22833590 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Michenfelder M, Hull WE, Retey J: Quantitative measurement of the error in the cryptic stereospecificity of methylmalonyl-CoA mutase. Eur J Biochem. 1987 Nov 2;168(3):659-67. Pubmed: 2889598 Link_out

Enzymes
Name: Methylmalonyl-CoA epimerase, mitochondrial
Reactions: Not Available
Gene Name: MCEE
Uniprot ID: Q96PE7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonyl-CoA mutase, mitochondrial
Reactions: Not Available
Gene Name: MUT
Uniprot ID: P22033 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA