ECMDB: 3-Methylcrotonyl-CoA (ECMDB01493) (M2MDB000401)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)Transporters (1)XML

Proteins (1206)

Record Information

Version

2.0

Creation Date

2012-05-31 13:53:30 -0600

Update Date

2015-06-03 15:54:09 -0600

Secondary Accession Numbers

ECMDB01493

Identification

Name:

3-Methylcrotonyl-CoA

Description

3-Methylcrotonyl-CoA is an essential metabolite for leucine metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

β-methylcrotonoyl-CoA
3-Methylbut-2-enoyl-CoA
3-Methylbut-2-enoyl-Coenzyme A
3-Methylcrotonoyl-CoA
3-Methylcrotonoyl-Coenzyme A
3-Methylcrotonyl-CoA
3-Methylcrotonyl-Coenzyme A
b-Methylcrotonoyl-CoA
b-Methylcrotonoyl-coenzyme A
b-Methylcrotonyl-CoA
B-Methylcrotonyl-CoA (HMDB01493
B-Methylcrotonyl-Coenzyme A
B-Methylcrotonyl-Coenzyme A (HMDB01493
Beta-Methylcrotonoyl-CoA
Beta-Methylcrotonoyl-Coenzyme A
Beta-Methylcrotonyl-CoA
Beta-Methylcrotonyl-CoA (HMDB01493
Beta-Methylcrotonyl-Coenzyme A
Beta-Methylcrotonyl-Coenzyme A (HMDB01493
Dimethylacryloyl-CoA
Dimethylacryloyl-Coenzyme A
β-Methylcrotonoyl-CoA
β-Methylcrotonoyl-coenzyme A
β-Methylcrotonyl-CoA
β-Methylcrotonyl-CoA (HMDB01493
β-Methylcrotonyl-coenzyme A
β-Methylcrotonyl-coenzyme A (HMDB01493

Chemical Formula:

C₂₆H₄₂N₇O₁₇P₃S

Weight:

Average: 849.635
Monoisotopic: 849.157073179

InChI Key:

BXIPALATIYNHJN-TVCSPYKZSA-N

InChI:

InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1

CAS number:

793193-48-3

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-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name:

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

SMILES:

CC(C)=CC(=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

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl 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
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.51 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-4.3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	186.81 m³·mol⁻¹	ChemAxon
Polarizability	75.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

3-Hydroxyisovaleryl-CoA <> 3-Methylcrotonyl-CoA + Water
5-Methyl-3-oxo-4-hexenoyl-CoA + Coenzyme A <> 3-Methylcrotonyl-CoA + Acetyl-CoA
Isovaleryl-CoA + ETF-Oxidized 3-Methylcrotonyl-CoA + ETF-Reduced
Coenzyme A + 5-Methyl-3-oxo-4-hexenoyl-CoA > Acetyl-CoA + 3-Methylcrotonyl-CoA

SMPDB Pathways:

Not Available

KEGG Pathways:

Geraniol degradation ec00281
Valine, leucine and isoleucine degradation ec00280

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000120-6c047fea21fac24e0423	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1912000000-1e69b9a4b44e8aac26c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-e356c983f19414fbc82c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-8930140450-c6626636d28643a91eac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6910010010-8348d44355d1e2c70b46	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-0bfd3b35a59a8c971903	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Wysocki SJ, Hahnel R: 3-Methylcrotonylglycine excretion in 3-hydroxy-3-methylglutaric aciduria. Clin Chim Acta. 1978 May 16;86(1):101-8. Pubmed: 657530

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15486
HMDB ID	HMDB01493
Pubchem Compound ID	439869
Kegg ID	C03069
ChemSpider ID	388909
Wikipedia ID	Methylcrotonyl-CoA
BioCyc ID	3-METHYL-CROTONYL-COA
EcoCyc ID	3-METHYL-CROTONYL-COA

Enzymes

Protein Details

1. 3-ketoacyl-CoA thiolase

General function:: Involved in acetyl-CoA C-acyltransferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadA
Uniprot ID:: P21151
Molecular weight:: 40876

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

2. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

Protein Details

3. Probable enoyl-CoA hydratase paaF

General function:: Involved in catalytic activity
Specific function:: Could possibly oxidize fatty acids using specific components
Gene Name:: paaF
Uniprot ID:: P76082
Molecular weight:: 27237

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.

Protein Details

4. 3-ketoacyl-CoA thiolase_

General function:: Involved in transferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:: fadI
Uniprot ID:: P76503
Molecular weight:: 46530

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

5. Fatty acid oxidation complex subunit alpha_

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:: fadJ
Uniprot ID:: P77399
Molecular weight:: 77072

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Transporters

Protein Details

1. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

3-Methylcrotonyl-CoA (ECMDB01493) (M2MDB000401)

Structure for #<Compound:0xa92b32e4>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters

Reactions