Common Name |
Methacrylyl-CoA
Description |
Methacrylyl-CoA is a metabolite in the valine, leucine and isoleucine degradation pathway and highly reacts with free thiol compounds (PMID 14684172 ; KEGG). Cirrhosis reslits 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 ).
Structure |
Synonyms |
Value |
Source |
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
Chemical Formlia |
C25H40N7O17P3S
Average Molecliar Weight |
835.608
Monoisotopic Molecliar Weight |
835.141423115
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)slifanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name |
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)slifanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number |
6008-91-9
SMILES |
CC(=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
InChI Identifier |
InChI=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 Key |
NPALUEYCDZWBOV-NNYIDDMCSA-N
Chemical Taxonomy |
Description |
This compound belongs to the class of chemical entities known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Lipids and lipid-like moleclies
Sub Class |
Fatty Acyls
Direct Parent |
Acyl CoAs
Alternative Parents |
Coenzyme A and derivatives
Purine ribonucleoside diphosphates
Ribonucleoside 3-phosphates
Pentose phosphates
Beta amino acids and derivatives
Glycosylamines
6-aminopurines
Monosaccharide phosphates
Organic pyrophosphates
Aminopyrimidines and derivatives
Monoalkyl phosphates
Primary aromatic amines
Imidolactams
N-acyl amines
N-substituted imidazoles
Oxolanes
Heteroaromatic compounds
Thioesters
Secondary alcohols
Carbothioic S-esters
Secondary carboxylic acid amides
Oxacyclic compounds
Slifenyl compounds
Azacyclic compounds
Hydrocarbon derivatives
Carbonyl compounds
Organic oxides
Organopnictogen compounds
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
Monosaccharide phosphate
Organic pyrophosphate
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Fatty amide
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Primary aromatic amine
Pyrimidine
Oxolane
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Thiocarboxylic acid ester
Carboxamide group
Carbothioic s-ester
Secondary carboxylic acid amide
Secondary alcohol
Slifenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Amine
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organoslifur compound
Organic oxygen compound
Organopnictogen compound
Primary amine
Organic oxide
Aromatic heteropolycyclic compound
Molecliar Framework |
Aromatic heteropolycyclic compounds
External Descriptors |
Not Available
Ontology |
Status |
Expected but 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 Emlisifiers
Cellliar locations |
Extracellliar
Membrane
Mitochondria
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility4.11 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity181.21 m3·mol-1ChemAxon
Polarizability73.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Spectrum Type |
Description |
Splash Key |
|
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-000i-1912000120-43e6bafbba6b6bab0398View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-000i-0912000000-599320c41cce75641963View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-000i-2911000000-53ae9df4445dfd4eb7d6View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-4930131150-65deb538cb1e798afaa9View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-003r-3910100000-5913bc83b63ee9f0b2b9View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-057i-5900100000-806bd274223a7dc2c783View in MoNA
Biological Properties |
Cellliar Locations |
Extracellliar
Membrane
Mitochondria
Biofluid Locations |
Not Available
Tissue Location |
Not Available
Pathways |
Name |
SMPDB Link |
KEGG Link |
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencySMP00137Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencySMP00138Not Available
3-hydroxyisobutyric acid dehydrogenase deficiencySMP00521Not Available
3-hydroxyisobutyric aciduriaSMP00522Not Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type ISMP00237Not Available
3-Methylglutaconic Aciduria Type ISMP00139Not Available
3-Methylglutaconic Aciduria Type IIISMP00140Not Available
3-Methylglutaconic Aciduria Type IVSMP00141Not Available
Beta-Ketothiolase DeficiencySMP00173Not Available
Isobutyryl-coa dehydrogenase deficiencySMP00523Not Available
Isovaleric acidemiaSMP00524Not Available
Isovaleric AciduriaSMP00238Not Available
Maple Syrup Urine DiseaseSMP00199Not Available
Methylmalonate Semialdehyde Dehydrogenase DeficiencySMP00384Not Available
Methylmalonic AciduriaSMP00200Not Available
Propionic AcidemiaSMP00236Not Available
Valine, Leucine and Isoleucine DegradationSMP00032map00280
Normal Concentrations |
Not Available |
Abnormal Concentrations |
|
Not Available
Associated Disorders and Diseases |
Disease References |
None
Associated OMIM IDs |
None
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
Not Available
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB022369
KNApSAcK ID |
Not Available
Chemspider ID |
389035
KEGG Compound ID |
C03460
BioCyc ID |
METHACRYLYL-COA
BiGG ID |
41895
Wikipedia Link |
Not Available
NuGOwiki Link |
HMDB01011
Metagene Link |
HMDB01011
METLIN ID |
5941
PubChem Compound |
440021
PDB ID |
1RX0
ChEBI ID |
27754
Product: SKF-96365 (hydrochloride)
References |
Synthesis Reference |
Hawes, John W.; Harper, Edwin T. Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA. Methods in Enzymology (2 |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Shimomura Y, Honda T, Goto H, Nonami T, Kurokawa T, Nagasaki M, Murakami T: Effects of liver failure on the enzymes in the branched-chain amino acid catabolic pathway. Biochem Biophys Res Commun. 2004 Jan 9;313(2):381-5. [PubMed:14684172 ]
- Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3. [PubMed:15922108 ]
- Taniguchi K, Nonami T, Nakao A, Harada A, Kurokawa T, Sugiyama S, Fujitsuka N, Shimomura Y, Hutson SM, Harris RA, Takagi H: The valine catabolic pathway in human liver: effect of cirrhosis on enzyme activities. Hepatology. 1996 Dec;24(6):1395-8. [PubMed:8938168 ]
|
Enzymes
- General function:
- Involved in acyl-CoA dehydrogenase activity
- Specific function:
- Not Available
- Gene Name:
- ACADS
- Uniprot ID:
- P16219
- Molecular weight:
- 44296.705
Reactions
Isobutyryl-CoA + Acceptor → Methacrylyl-CoA + Reduced acceptor |
details |
- General function:
- Involved in acyl-CoA dehydrogenase activity
- Specific function:
- This enzyme is specific for acyl chain lengths of 4 to 16.
- Gene Name:
- ACADM
- Uniprot ID:
- P11310
- Molecular weight:
- 46587.98
Reactions
Isobutyryl-CoA + Acceptor → Methacrylyl-CoA + Reduced acceptor |
details |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Not Available
- Gene Name:
- EHHADH
- Uniprot ID:
- Q08426
- Molecular weight:
- 69153.26
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA |
details |
- General function:
- Involved in catalytic activity
- Specific function:
- Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
- Gene Name:
- ECHS1
- Uniprot ID:
- P30084
- Molecular weight:
- 31387.085
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA |
details |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Bifunctional subunit.
- Gene Name:
- HADHA
- Uniprot ID:
- P40939
- Molecular weight:
- 82998.97
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA |
details |
- General function:
- Involved in acyl-CoA dehydrogenase activity
- Specific function:
- Has greatest activity toward short branched chain acyl-CoA derivative such as (s)-2-methylbutyryl-CoA, isobutyryl-CoA, and 2-methylhexanoyl-CoA as well as toward short straight chain acyl-CoAs such as butyryl-CoA and hexanoyl-CoA. Can use valproyl-CoA as substrate and may play a role in controlling the metabolic flux of valproic acid in the development of toxicity of this agent.
- Gene Name:
- ACADSB
- Uniprot ID:
- P45954
- Molecular weight:
- 47485.035
Reactions
Isobutyryl-CoA + Acceptor → Methacrylyl-CoA + Reduced acceptor |
details |
- General function:
- Involved in acyl-CoA dehydrogenase activity
- Specific function:
- Has very high activity toward isobutyryl-CoA. Is an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Plays a role in transcriptional coactivation within the ARC complex.
- Gene Name:
- ACAD8
- Uniprot ID:
- Q9UKU7
- Molecular weight:
- 45069.39
Reactions
Isobutyryl-CoA + Acceptor → Methacrylyl-CoA + Reduced acceptor |
details |
PMID: 16302795