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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 UTC
HMDB IDHMDB0059619
Secondary Accession Numbers
  • HMDB59619
Metabolite Identification
Common Name(S)-ethylmalonyl-CoA
Description(S)-ethylmalonyl-CoA, also known as ethylmalonyl-coenzyme A or etmal-CoA, 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. Thus, (S)-ethylmalonyl-CoA is considered to be a fatty ester lipid molecule (S)-ethylmalonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563865956
Synonyms
ValueSource
(2S)-2-Ethylmalonyl-CoAChEBI
(2S)-Ethylmalonyl coenzyme AChEBI
(S)-2-Ethylmalonyl-CoAChEBI
(S)-Ethylmalonyl coenzyme AChEBI
Ethylmalonyl-CoAKegg
Ethylmalonyl coenzyme AKegg
EtMal-CoAHMDB
Ethylmalonyl-coenzyme AHMDB
(S)-Ethylmalonyl-CoAKEGG
Chemical FormulaC26H42N7O19P3S
Average Molecular Weight881.633
Monoisotopic Molecular Weight881.146902423
IUPAC Name(2S)-2-[({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)carbonyl]butanoic acid
Traditional Name(2S)-2-[({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)carbonyl]butanoic acid
CAS Registry NumberNot Available
SMILES
CC[C@@H](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@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C26H42N7O19P3S/c1-4-13(24(38)39)25(40)56-8-7-28-15(34)5-6-29-22(37)19(36)26(2,3)10-49-55(46,47)52-54(44,45)48-9-14-18(51-53(41,42)43)17(35)23(50-14)33-12-32-16-20(27)30-11-31-21(16)33/h11-14,17-19,23,35-36H,4-10H2,1-3H3,(H,28,34)(H,29,37)(H,38,39)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t13-,14+,17+,18+,19-,23+/m0/s1
InChI KeyVUGZQVCBBBEZQE-UQCJFRAESA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
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
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Secondary alcohol
  • Amino acid
  • Carboxamide group
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.57 g/LALOGPS
logP-0.25ALOGPS
logP-3.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area407.91 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity188.77 m³·mol⁻¹ChemAxon
Polarizability79.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-237.15730932474
DeepCCS[M+Na]+210.74130932474
AllCCS[M+H]+260.432859911
AllCCS[M+H-H2O]+260.932859911
AllCCS[M+NH4]+259.932859911
AllCCS[M+Na]+259.732859911
AllCCS[M-H]-258.432859911
AllCCS[M+Na-2H]-262.632859911
AllCCS[M+HCOO]-267.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-ethylmalonyl-CoACC[C@@H](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@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C125451.5Standard polar33892256
(S)-ethylmalonyl-CoACC[C@@H](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@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C124607.1Standard non polar33892256
(S)-ethylmalonyl-CoACC[C@@H](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@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C126511.3Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 10V, Positive-QTOFsplash10-01p9-1930000120-ee5f7e92330c04bb578a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 20V, Positive-QTOFsplash10-000l-0911000000-798173e67ae983a4cab52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 40V, Positive-QTOFsplash10-000i-2920000000-4241b8498e3379a656792017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 10V, Negative-QTOFsplash10-02ai-6900031450-403495d2e5a97045a55f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 20V, Negative-QTOFsplash10-001i-5910120030-9754df7ee709012a8d9c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-20d123d5f49aa9556ef42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 10V, Negative-QTOFsplash10-0019-0000000390-ef2260e0f0c1fd93864b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 20V, Negative-QTOFsplash10-0gba-6600004900-ff4ae3e29a0b7fe7cba62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 40V, Negative-QTOFsplash10-0fi0-4303507900-cbc4b98980f39175eed22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 10V, Positive-QTOFsplash10-03di-0000000190-89843e625494dcff3c962021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 20V, Positive-QTOFsplash10-01pt-0000000590-b9f0dad17536a0f961292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-ethylmalonyl-CoA 40V, Positive-QTOFsplash10-004i-0039000000-2cc2e670c392fa4a797b2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18026
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49852422
PDB IDNot Available
ChEBI ID60907
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
MCEE
Uniprot ID:
Q96PE7
Molecular weight:
18748.755
Reactions
(S)-ethylmalonyl-CoA → (2R)-Ethylmalonyl-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)-ethylmalonyl-CoA → Butyryl-CoA + CO(2)details