L-Acetylcarnitine (YMDB00351)

Identification

YMDB ID

YMDB00351

Name

L-Acetylcarnitine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

L-Acetylcarnitine, also known as alcar or branigen, 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. Thus, L-acetylcarnitine is considered to be a fatty ester. Based on a literature review a significant number of articles have been published on L-Acetylcarnitine.

Structure

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

Synonyms

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

CAS number

3040-38-8

Weight

Average: 203.2356
Monoisotopic: 203.115758037

InChI Key

RDHQFKQIGNGIED-UHFFFAOYSA-N

InChI

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

IUPAC Name

(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

Traditional IUPAC Name

acetyl-L-carnitine

Chemical Formula

C₉H₁₇NO₄

SMILES

[H]C([H])([H])C(=O)OC([H])(C([H])([H])C([O-])=O)C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

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 salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acetylcarnitine (CHEBI:57589 )
O-acyl-L-carnitine (CHEBI:57589 )

Physical Properties

State

Solid

Charge

Melting point

145 °C

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.82 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

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

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	splash10-00di-9100000000-c3bf4495e8c4abf714db	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-71230651236adb31fa6f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9050000000-2a63f200e23202870ebe	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	JSpectraViewer
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	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
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:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834

Synthesis Reference:

Gu, Heng-da; Shi, Shuang; Yang, Ying; Shi, Zhao-xin; Yu, Zhan-long. Synthesis of acetyl-L-carnitine by direct acylation method. Shenyang Huagong Xueyuan Xuebao (2006), 20(2), 154-155, 160.

External Links:

Resource	Link
CHEBI ID	57589
HMDB ID	HMDB00201
Pubchem Compound ID	18230
Kegg ID	C02571
ChemSpider ID	21243783
FOODB ID	FDB093666
Wikipedia	Acetylcarnitine
BioCyc ID	(-)o-acetylcarnitine

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.

Structure for #<Compound:0xb3dcb190>

Enzymes

Reactions

Reactions

Reactions