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Human Metabolome Database Version 3.5

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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 | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
    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
    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:
    • (R)-methylmalonyl-CoA = (S)-methylmalonyl-CoA [RN:R02765]
    Gene Name: MCEE
    Uniprot ID: Q96PE7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Methylmalonyl-CoA mutase, mitochondrial
    Reactions:
    • (R)-methylmalonyl-CoA = succinyl-CoA [RN:R00833]
    Gene Name: MUT
    Uniprot ID: P22033 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA