Hexadecanoylcarnitine (YMDB01534)

Identification

YMDB ID

YMDB01534

Name

Hexadecanoylcarnitine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Hexadecanoylcarnitine (palmitoylcarnitine) is a long-chain fatty acid ester of carnitine with palmitoleic acid. Carnitine is used for the transport of fatty acids during beta-oxidation, during what fatty acids are broken down to acetyl-CoA. Acetyl-CoA is then used in the glyoxylate cycle for gluconeogenesis and formation of carbohydrates, or transported to mitochondrion for the generation of metabolic energy through the citric acid cycle. [Biocyc PWY-6111]

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-Palmitoylcarnitine
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid
(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoate
(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoic acid
(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoate
(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid
3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium
D-Palmitylcarnitine
Hexadecanoyl-L-carnitine
Hexadecanoylcarnitine
Hexadecenoyl carnitine
L-Carnitine palmitoyl ester
L-Palmitoyl-L-carnitine
L-Palmitoylcarnitine
L(-)-Palmitylcarnitine
O-Hexadecanoyl-(R)-carnitine
O-Hexadecanoyl-R-carnitine
Palmitoyl D-carnitine
Palmitoyl-(-)-carnitine
Palmitoyl-L-carnitine
Palmityl-L-carnitine
Palmitylcarnitine
Palmitoylcarnitine
(2R)-Palmitoylcarnitine
C16 Carnitine

CAS number

18877-64-0

Weight

Average: 399.6077
Monoisotopic: 399.334858933

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-N

InChI

InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

palmitoylcarnitine

Chemical Formula

C₂₃H₄₅NO₄

SMILES

CCCCCCCCCCCCCCCC(=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 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-acyl-L-carnitine (CHEBI:17490 )
O-palmitoylcarnitine (CHEBI:17490 )
Fatty acyl carnitines (C02990 )
Fatty acyl carnitines (LMFA07070004 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	1.2e-05 g/L	ALOGPS
logP	1.77	ALOGPS
logP	2.03	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	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	20	ChemAxon
Refractivity	137.08 m³·mol⁻¹	ChemAxon
Polarizability	50.35 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

Fatty acid metabolism

PW002460

KEGG Pathways

Fatty acid metabolism

ec00071

SMPDB Reactions

Palmityl-CoA + (R)-Carnitine ↔ Hexadecanoylcarnitine + Coenzyme A

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
0.4 ± 0.0 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

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-9220000000-890219021b84f6894540	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 (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, Positive (Annotated)	splash10-0udi-1000900000-109f35c9819eb5eed7b7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-9d6bb14eddb4cfa8341a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-87b1d0debe4e0cb7bd31	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0139500000-21c36c851939b94d4523	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0029600000-69ebe292c2ce42c8d810	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-197944fd1aa4ac44bdd2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000613900-006582b143e5906e51cc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000614900-14a5d773f652b71671fb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-b0528be9c13e412551af	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-b54b0a7f2164f15f15f2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9000500000-d7434e08a3e0942fa2e9	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	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:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17490
HMDB ID	HMDB00222
Pubchem Compound ID	11953816
Kegg ID	C02990
ChemSpider ID	10128117
FOODB ID	FDB021910
Wikipedia ID	Palmitoylcarnitine
BioCyc ID	CPD-419

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. 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:0xa77b74cc>

Enzymes

Reactions

Reactions