O-acetylcarnitinium (YMDB00617)

Identification

YMDB ID

YMDB00617

Name

O-acetylcarnitinium

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

O-acetylcarnitinium belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. O-acetylcarnitinium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

O-Acetyl-L-carnitine
O-Acetylcarnitine
(-)-Acetylcarnitine
(R)-Acetylcarnitine
Acetyl-L-(-)-carnitine
Acetyl-L-carnitine
L-Acetylcarnitine
L-Carnitine acetyl ester
L-O-Acetylcarnitine
O-Acetyl-(R)-carnitine
R-Acetylcarnitine
Branigen
Levocarnitine acetyl
Acetyl carnitine
Carnitine, acetyl
Alcar
Acetyl L carnitine
Acetylcarnitine, (R)-isomer
Medosan
ALC
3-(Acetyloxy)-4-(trimethylammonio)butanoate
Acetyl-DL-carnitine
Acetylcarnitine
DL-O-Acetylcarnitine
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid
(+-)-Acetylcarnitine
Acetyl-carnitine
Nicetile
(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate
C2 Carnitine
Acylcarnitine C2:0
C2:0 Carnitine

CAS number

Not Available

Weight

Average: 204.2435
Monoisotopic: 204.123583069

InChI Key

RDHQFKQIGNGIED-MRVPVSSYSA-O

InChI

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/p+1/t8-/m1/s1

IUPAC Name

[(2R)-2-(acetyloxy)-3-carboxypropyl]trimethylazanium

Traditional IUPAC Name

(+-)-acetylcarnitine

Chemical Formula

C₉H₁₈NO₄

SMILES

CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Amine
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:15960 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
logP	-4.4	ChemAxon
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.8 m³·mol⁻¹	ChemAxon
Polarizability	21.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
peroxisome
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

(R)-Carnitine + Acetyl-CoA ↔ O-acetylcarnitinium + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9400000000-d53cbc72a0b9e219206d	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-3930000000-1af0468e51346890699f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15960
HMDB ID	HMDB0000201
Pubchem Compound ID	439756
Kegg ID	C02571
ChemSpider ID	388815
FOODB ID	FDB093666
Wikipedia ID	Acetyl-L-carnitine
BioCyc ID	Not Available

Enzymes

Protein Details

1. Carnitine O-acetyltransferase, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Carnitine acetylase is specific for short chain fatty acids. Carnitine acetylase seems to affect the flux through the pyruvate dehydrogenase complex. It may be involved as well in the transport of acetyl-CoA into mitochondria
Gene Name:: CAT2
Uniprot ID:: P32796
Molecular weight:: 77241.20313

Reactions

Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.

Protein Details

2. Putative mitochondrial carnitine O-acetyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Involved in the transfer of acetyl-CoA into mitochondria. May also be involved in the metabolism of acetate and of ethanol
Gene Name:: YAT1
Uniprot ID:: P80235
Molecular weight:: 77764.79688

Reactions

Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.

Protein Details

3. Carnitine O-acetyltransferase YAT2

General function:: Involved in acyltransferase activity
Specific function:: Involved in the shutteling of acetyl-CoA in the cell
Gene Name:: YAT2
Uniprot ID:: P40017
Molecular weight:: 103333.0

Reactions

Acetyl-CoA + carnitine → CoA + O-acetylcarnitine.

Transporters

Protein Details

1. Mitochondrial carnitine carrier

General function:: Involved in binding
Specific function:: Transports carnitine, acetylcarnitine, propionylcarnitine and to a much lower extent medium- and long- chain acylcarnitines
Gene Name:: CRC1
Uniprot ID:: Q12289
Molecular weight:: 34753.89844

Structure for #<Compound:0xa8fc7788>

Enzymes

Reactions

Reactions

Reactions

Transporters