2-methylacetoacetyl-CoA (PAMDB120189)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120189
Identification
Name: 2-methylacetoacetyl-CoA
Description:An acyl-CoA(4−) that is the tetraanion of 2-methylacetoacetyl-CoA, arising from deprotonation of phosphate and diphosphate functions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-methyl-3-oxobutanoyl-CoA
  • 2-methylacetoacetyl-CoA tetraanion
  • 2-methylacetoacetyl-coenzyme A(4−)
Chemical Formula: C26H38N7O18P3S
Average Molecular Weight: 861.604
Monoisotopic Molecular Weight: 865.152
InChI Key: NHNODHRSCRALBF-UHFFFAOYSA-J
InChI:InChI=1S/C26H42N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-13,15,18-20,24,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/p-4
CAS number: 6712-01-2
IUPAC Name:3'-phosphonatoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methyl-3-oxobutanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl]diphosphate}
Traditional IUPAC Name: 2-methylacetoacetyl-coa
SMILES:CC(C(SCCNC(CCNC(=O)C(C(C)(C)COP(=O)(OP([O-])(=O)OCC3(C(C(C(N2(C=NC1(C(=NC=NC=12)N)))O3)O)OP([O-])([O-])=O))[O-])O)=O)=O)C(=O)C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent 3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Organic pyrophosphate
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • Pyrimidine
  • 1,3-dicarbonyl compound
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.56 mg/mLALOGPS
logP-0.3ALOGPS
logP-6.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity186.68 m3·mol-1ChemAxon
Polarizability76.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
2-methylacetoacetyl-CoA + coenzyme A → propanoyl-CoA + acetyl-CoA
NAD+ + 2-methyl-3-hydroxybutyryl-CoA → Hydrogen ion + NADH + 2-methylacetoacetyl-CoA
Pathways:
  • Valine, Leucine and Isoleucine Degradation pae00280
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-5f327e333328fcc70202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1913000000-650b2ea011795e9bf110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-6bbf6c241dd6d98b053cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00nb-9711030540-eef9a46a054a7b270589View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4910110010-e2d95b02d06d6a01ee2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-d40d902d22d384d0d334View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
METABOLIGHTSMTBLC57335
HMDBHMDB01157
CHEBI57335
PUBCHEM25244541
LIGAND-CPDC03344
CAS6712-01-2