Bovine Metabolome Database: Showing metabocard for L-Palmitoylcarnitine (BMDB0000222)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:58 UTC

Update Date

2020-06-04 20:42:28 UTC

BMDB ID

BMDB0000222

Secondary Accession Numbers

BMDB00222

Metabolite Identification

Common Name

L-Palmitoylcarnitine

Description

L-Palmitoylcarnitine, also known as hexadecanoylcarnitine or C16 carnitine, 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-palmitoylcarnitine is considered to be a fatty ester lipid molecule. L-Palmitoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Palmitoylcarnitine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₃H₄₅NO₄

Average Molecular Weight

399.6077

Monoisotopic Molecular Weight

399.334858933

IUPAC Name

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

Traditional Name

palmitoylcarnitine

CAS Registry Number

2364-67-2

SMILES

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

InChI Identifier

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

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9220000000-890219021b84f6894540	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-1000900000-109f35c9819eb5eed7b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-9d6bb14eddb4cfa8341a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-87b1d0debe4e0cb7bd31	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0139500000-21c36c851939b94d4523	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0029600000-69ebe292c2ce42c8d810	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-197944fd1aa4ac44bdd2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000613900-006582b143e5906e51cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000614900-14a5d773f652b71671fb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-b0528be9c13e412551af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-b54b0a7f2164f15f15f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9000500000-d7434e08a3e0942fa2e9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane
Mitochondria

Biospecimen Locations

Blood
Liver
Longissimus Thoracis Muscle
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fatty Acid Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.02 +/- 0.01 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Liver	Detected and Quantified	0.012 +/- 0.004 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.02 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.016 +/- 0.004 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.011 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.04 +/- 0.015 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.01 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.03 +/- 0.004 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	0.028 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.027 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.036 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.029 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	0.02 +/- 0.012 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semimembranosus Muscle	Detected and Quantified	0.009 +/- 0.004 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.02 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000222

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021910

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17490

References

Synthesis Reference

Norum, Kaare R. Palmityl coenzyme A-carnitine palmityltransferase. Purification from calf-liver mitochondria and some properties of the enzyme. Biochimica et Biophysica Acta, Specialized Section on Enzymological Subjects (1964), 89(1), 95-108.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carnitine O-palmitoyltransferase 1, muscle isoform

General function:: Involved in carnitine O-palmitoyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1B
Uniprot ID:: Q58DK1
Molecular weight:: 88512.0

Reactions

Palmityl-CoA + L-Carnitine → L-Palmitoylcarnitine + Coenzyme A	details

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in carnitine O-palmitoyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: Q2KJB7
Molecular weight:: 74483.0

Reactions

Palmityl-CoA + L-Carnitine → L-Palmitoylcarnitine + Coenzyme A	details

Showing metabocard for L-Palmitoylcarnitine (BMDB0000222)

Structure for BMDB0000222 (L-Palmitoylcarnitine)

Enzymes

Reactions

Reactions