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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2019-07-23 05:45:27 UTC
HMDB IDHMDB0002310
Secondary Accession Numbers
  • HMDB02310
Metabolite Identification
Common NameS-Methylmalonyl-CoA
DescriptionMethylmalonyl-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
Data?1563860727
Synonyms
ValueSource
(S)-Methylmalonyl-CoAHMDB
(S)-Methylmalonyl-coenzyme AHMDB
Chemical FormulaC25H40N7O19P3S
Average Molecular Weight867.607
Monoisotopic Molecular Weight867.131252359
IUPAC Name(2S)-3-[(2-{3-[(2R)-3-[({[({[(3S,4R)-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 Name(2S)-3-[(2-{3-[(2R)-3-{[({[(3S,4R)-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 Number73173-91-8
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@H](O)[C@@H]1OP(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?/m0/s1
InChI KeyMZFOKIKEPGUZEN-JDVCRUKVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentSophorolipids
Alternative Parents
Substituents
  • Sophorolipid
  • Diterpene glycoside
  • Diterpenoid
  • Terpene glycoside
  • Long-chain fatty acid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Oxane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.57 g/LALOGPS
logP-0.6ALOGPS
logP-6.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.97ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.13 m³·mol⁻¹ChemAxon
Polarizability76.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4911000020-c392edc35bfe7a605c16JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-d7d73fa71a22c4b9e10cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-1c3ee05de5b5cf1c067cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00nb-9811140550-fade85d2dd723fe43fdaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5911110010-2c7ce12039a0e299c300JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-5900100000-48f1904d8b30fe71d5e4JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022959
KNApSAcK IDNot Available
Chemspider ID13628334
KEGG Compound IDC00683
BioCyc IDNot Available
BiGG ID35689
Wikipedia LinkMethylmalonyl-CoA
METLIN ID6609
PubChem Compound21252287
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMutka, Sarah C.; Bondi, Shana M.; Carney, John R.; Da Silva, Nancy A.; Kealey, James T. Metabolic pathway engineering for complex polyketide biosynthesis in Saccharomyces cerevisiae .FEMS Yeast Research (2006), 6(1), 40-47.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
MCEE
Uniprot ID:
Q96PE7
Molecular weight:
18748.755
Reactions
Methylmalonyl-CoA → S-Methylmalonyl-CoAdetails
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular weight:
58215.13
Reactions
Adenosine triphosphate + Propionyl-CoA + Hydrogen carbonate → ADP + Phosphate + S-Methylmalonyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PCCA
Uniprot ID:
P05165
Molecular weight:
80058.295
Reactions
Adenosine triphosphate + Propionyl-CoA + Hydrogen carbonate → ADP + Phosphate + S-Methylmalonyl-CoAdetails
General function:
Not Available
Specific function:
Decarboxylases ethylmalonyl-CoA decarboxylase, a potentially toxic metabolite, to form butyryl-CoA, suggesting it might be involved in metabolite proofreading. Also has methylmalonyl-CoA decarboxylase activityx at lower level.
Gene Name:
ECHDC1
Uniprot ID:
Q9NTX5
Molecular weight:
32996.93
Reactions
S-Methylmalonyl-CoA → Propionyl-CoA + CO(2)details