Record Information
Version1.0
Creation date2011-09-21 00:12:53 UTC
Update date2015-07-21 06:57:10 UTC
Primary IDFDB022369
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethacrylyl-CoA
DescriptionMethacrylyl-CoA is a metabolite in the valine, leucine and isoleucine degradation pathway and highly reacts with free thiol compounds (PMID 14684172; KEGG). Cirrhosis results in a significant decrease in 3--hydroxyisobutyryl-CoA hydrolase activity, a key enzyme in the valine catabolic pathway that plays an important role in the catabolism of a potentially toxic compound, methacrylyl-CoA, formed as an intermediate in the catabolism of valine and isobutyrate. (PMID: 8938168) [HMDB]
CAS Number6008-91-9
Structure
Thumb
Synonyms
SynonymSource
2-Methylprop-2-enoyl-CoAHMDB
2-Methylprop-2-enoyl-coenzyme AHMDB
Methacrylyl CoAHMDB
Methacrylyl coenzyme AHMDB
Methacrylyl-coenzyme AHMDB
Methylacrylyl-CoAHMDB
Methylacrylyl-coenzyme AHMDB
S-(2-Methyl-2-propenoateHMDB
S-(2-Methyl-2-propenoate) CoAHMDB
S-(2-Methyl-2-propenoate) coenzyme AHMDB
S-(2-Methyl-2-propenoic acidHMDB
2-Methylprop-2-enoyl-Coenzyme Ahmdb
methacrylyl CoAhmdb
methacrylyl Coenzyme Ahmdb
Methacrylyl-coenzyme ahmdb
methylacrylyl-CoAhmdb
methylacrylyl-Coenzyme Ahmdb
s-(2-methyl-2-propenoatehmdb
s-(2-methyl-2-propenoate) CoAhmdb
s-(2-methyl-2-propenoate) Coenzyme Ahmdb
s-(2-methyl-2-propenoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility4.11 g/LALOGPS
logP-0.38ALOGPS
logP-5.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity181.21 m³·mol⁻¹ChemAxon
Polarizability73.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H40N7O17P3S
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1
InChI KeyNPALUEYCDZWBOV-NNYIDDMCSA-N
Isomeric SMILESCC(=C)C(=O)SCCNC(=O)CCNC(=O)C(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=C1N=CN=C2N
Average Molecular Weight835.608
Monoisotopic Molecular Weight835.141423115
Classification
Description belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Fatty amide
  • N-acyl-amine
  • Pyridine
  • Fatty acyl
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-43e6bafbba6b6bab0398JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0912000000-599320c41cce75641963JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-53ae9df4445dfd4eb7d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4930131150-65deb538cb1e798afaa9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3910100000-5913bc83b63ee9f0b2b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-806bd274223a7dc2c783JSpectraViewer
ChemSpider ID389035
ChEMBL IDNot Available
KEGG Compound IDC03460
Pubchem Compound ID440021
Pubchem Substance IDNot Available
ChEBI ID27754
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01011
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41895
KNApSAcK IDNot Available
HET ID1RX0
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Enoyl-CoA hydratase, mitochondrialECHS1P30084
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference