ECMDB: L-Carnitinyl-CoA (ECMDB20578) (M2MDB001380)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (23)

Record Information

Version

2.0

Creation Date

2012-05-31 14:51:34 -0600

Update Date

2015-06-04 18:01:01 -0600

Secondary Accession Numbers

ECMDB20578

Identification

Name:

L-Carnitinyl-CoA

Description

L-carnitinyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. L-carnityl-CoA is involved in carnitine metabolism

Structure

MOL SDF PDB SMILES InChI

Synonyms:

D-Carnitinyl-coa
L-Carnityl-coa

Chemical Formula:

C₂₈H₅₀N₈O₁₈P₃S

Weight:

Average: 911.726
Monoisotopic: 911.217662062

InChI Key:

BBRISSLDTUHWKG-UHFFFAOYSA-O

InChI:

InChI=1S/C28H49N8O18P3S/c1-28(2,23(41)26(42)31-7-6-18(38)30-8-9-58-19(39)10-16(37)11-36(3,4)5)13-51-57(48,49)54-56(46,47)50-12-17-22(53-55(43,44)45)21(40)27(52-17)35-15-34-20-24(29)32-14-33-25(20)35/h14-17,21-23,27,37,40-41H,6-13H2,1-5H3,(H7-,29,30,31,32,33,38,42,43,44,45,46,47,48,49)/p+1

CAS number:

Not Available

IUPAC Name:

[4-({2-[(3-{[4-({[({[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)-2-hydroxy-4-oxobutyl]trimethylazanium

Traditional IUPAC Name:

{4-[(2-{[3-({4-[({[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]-2-hydroxy-4-oxobutyl}trimethylazanium

SMILES:

CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CC(O)C[N+](C)(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Monosaccharide
Alpha-hydroxyaldehyde
Secondary alcohol
1,2-diol
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Primary alcohol
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glyceraldehyde (CHEBI:27975 )
Aldoses (C02426 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.72 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-8.8	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	390.84 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	213.26 m³·mol⁻¹	ChemAxon
Polarizability	84.68 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
L-Carnitinyl-CoA <> D-Carnitinyl-CoA
Adenosine triphosphate + Coenzyme A + Carnitine > ADP + L-Carnitinyl-CoA + Phosphate
Carnitine + Crotonobetainyl-CoA <> L-Carnitinyl-CoA + Crotonobetaine
gamma-Butyrobetainyl-CoA + Carnitine <> L-Carnitinyl-CoA + gamma-Butyrobetaine
L-Carnitinyl-CoA > Crotonobetainyl-CoA + Water
Coenzyme A + Carnitine + Adenosine triphosphate > L-Carnitinyl-CoA + Adenosine monophosphate + Pyrophosphate
Carnitine + gamma-Butyrobetainyl-CoA > L-Carnitinyl-CoA + gamma-Butyrobetaine
L-Carnitinyl-CoA <> (E)-4-(Trimethylammonio)but-2-enoyl-CoA + Water
(E)-4-(Trimethylammonio)but-2-enoyl-CoA + L-Carnitine + 4-Trimethylammoniobutanoyl-CoA <> Crotonobetaine + L-Carnitinyl-CoA + gamma-Butyrobetaine

SMPDB Pathways:

Not Available

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-1931220230-e52d91f4884c00ba801f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0940200000-0668fa03846bd3b54f4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910101000-38b8fba9fc2e0e0f772b	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	Not Available
HMDB ID	Not Available
Pubchem Compound ID	605
Kegg ID	C20750
ChemSpider ID	585
Wikipedia ID	Not Available
BioCyc ID	L-CARNITINYL-COA
EcoCyc ID	L-CARNITINYL-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. 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

L-Carnitinyl-CoA (ECMDB20578) (M2MDB001380)

Structure for #<Compound:0xaece5730>

Enzymes

Reactions