ECMDB: Crotonobetainyl-CoA (ECMDB20539) (M2MDB001346)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (4)

Record Information

Version

2.0

Creation Date

2012-05-31 14:49:40 -0600

Update Date

2015-06-03 17:20:11 -0600

Secondary Accession Numbers

ECMDB20539

Identification

Name:

Crotonobetainyl-CoA

Description

Crotonobetainyl-coa belongs to the class of Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(9R,20E)-1-(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl-3,5,9-trihydroxy-N,N,N,8,8-pentamethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosph adocos-20-en-22-aminium 3,5-dioxide (non-preferred name)
(E)-4-(trimethylammonio)but-2-enoyl-coenzyme A
(E)-4-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulfanyl-4-oxobut-2-enyl-trimethylazanium
(e)-4-2-3-(2R)-4-(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-ylmethoxy-hydroxyphosphoryloxy-hydroxyphosphoryloxy-2-hydroxy-3,3-dimethylbutanoylaminopropanoylaminoethylsulphanyl-4-oxobut-2-enyl-trimethylazanium
Crotonobetainyl-CoA
Crotonobetainyl-coenzyme A

Chemical Formula:

C₂₈H₄₈N₈O₁₇P₃S

Weight:

Average: 893.71
Monoisotopic: 893.207097376

InChI Key:

WAUPBDVHJXXZGW-HXPULJKESA-O

InChI:

InChI=1S/C28H47N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h6-7,15-17,21-23,27,39-40H,8-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1/b7-6+/t17-,21-,22-,23+,27-/m1/s1

CAS number:

Not Available

IUPAC Name:

[(2E)-4-({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)-4-oxobut-2-en-1-yl]trimethylazanium

Traditional IUPAC Name:

[(2E)-4-({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)-4-oxobut-2-en-1-yl]trimethylazanium

SMILES:

[H]\C(C[N+](C)(C)C)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@@](O)([H])[C@]1([H])OP(=O)(O)O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Pentose phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
Organic pyrophosphate
Pentose monosaccharide
Monosaccharide phosphate
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Fatty amide
Imidolactam
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
Quaternary ammonium salt
Heteroaromatic compound
Imidazole
Azole
Tetraalkylammonium salt
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carbothioic s-ester
Amino acid or derivatives
Carboxylic acid derivative
Sulfenyl compound
Organoheterocyclic compound
Oxacycle
Thiocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Organic salt
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA (CHEBI:61123 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.74 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-7.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	212.99 m³·mol⁻¹	ChemAxon
Polarizability	82.51 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:

L-Carnitinyl-CoA <> Crotonobetainyl-CoA + Water
Adenosine triphosphate + Coenzyme A + Crotonobetaine > ADP + Crotonobetainyl-CoA + Phosphate
Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine
L-Carnitinyl-CoA > Crotonobetainyl-CoA + Water
gamma-Butyrobetainyl-CoA + an oxidized electron acceptor <> Crotonobetainyl-CoA + a reduced electron acceptor
Crotonobetainyl-CoA + reduced electron acceptor > gamma-Butyrobetainyl-CoA + oxidized electron acceptor
D-Carnitinyl-CoA > Crotonobetainyl-CoA + Water

SMPDB Pathways:

L-carnitine degradation I

PW002037

KEGG Pathways:

Not Available

EcoCyc Pathways:

carnitine degradation I CARNMET-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1923030130-cf2c21224ca3946d70dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0932000000-a7b012b71b0c16ec17aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-54da84e88cbcc84e3754	View in MoNA
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:

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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	61123
HMDB ID	Not Available
Pubchem Compound ID	591
Kegg ID	Not Available
ChemSpider ID	571
Wikipedia ID	Not Available
BioCyc ID	CROTONOBETAINYL-COA
EcoCyc ID	CROTONOBETAINYL-COA

Enzymes

Protein Details

1. Carnitinyl-CoA dehydratase

General function:: Involved in hydro-lyase activity
Specific function:: Catalyzes the reversible dehydration of L-carnitinyl-CoA to crotonobetainyl-CoA
Gene Name:: caiD
Uniprot ID:: P31551
Molecular weight:: 28190

Reactions

L-carnitinyl-CoA = H(2)O + crotonobetainyl-CoA.

Protein Details

2. Crotonobetainyl-CoA:carnitine CoA-transferase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reversible transfer of the CoA moiety from gamma-butyrobetainyl-CoA to L-carnitine to generate L-carnitinyl- CoA and gamma-butyrobetaine. Is also able to catalyze the reversible transfer of the CoA moiety from gamma-butyrobetainyl- CoA or L-carnitinyl-CoA to crotonobetaine to generate crotonobetainyl-CoA
Gene Name:: caiB
Uniprot ID:: P31572
Molecular weight:: 45126

Protein Details

3. Crotonobetainyl-CoA dehydrogenase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the reduction of crotonobetainyl-CoA to gamma- butyrobetainyl-CoA
Gene Name:: caiA
Uniprot ID:: P60584
Molecular weight:: 42558

Protein Details

4. Probable crotonobetaine/carnitine-CoA ligase

General function:: Involved in catalytic activity
Specific function:: Could catalyze the transfer of CoA to carnitine, generating the initial carnitinyl-CoA needed for the CaiB reaction cycle
Gene Name:: caiC
Uniprot ID:: P31552
Molecular weight:: 58559

Crotonobetainyl-CoA (ECMDB20539) (M2MDB001346)

Structure for #<Compound:0xa8c50a14>

Enzymes

Reactions