MiMeDB: Showing metabocard for Palmitoylcarnitine (MMDBc0000505)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:18 UTC

Update Date

2024-04-30 19:32:41 UTC

Metabolite ID

MMDBc0000505

Metabolite Identification

Common Name

Palmitoylcarnitine

Description

L-Palmitoylcarnitine or hexadecanoylcarnitine is an acylcarnitine. It is technically a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. The general role of acylcarnitines is to transport acyl-groups, organic acids and fatty acids, from the cytoplasm into the mitochondria so that they can be broken down to produce energy. As part of this process, palmitic acid is first transported into the cell via the long-chain fatty acid transport protein 1 (FATP1). Once inside the cell it undergoes a reaction to form an acyl-CoA derivative called palmitoyl-CoA. This reaction is facilitated by the Long-chain fatty-acid CoA ligase 1 protein, which adds a CoA moiety to appropriate acyl groups. Many acyl-CoA groups will then further react with other zwitterionic compounds such as carnitine (to form acylcarnitines) and amino acids (to form acyl amides). The carnitine needed to form acylcarnitines inside the cell is transported into the cell by the organic cation/carnitine transporter 2. In forming an acylcarnitine derivative, palmitoyl-CoA reacts with L-carnitine to form palmitoylcarnitine. This reaction is catalyzed by carnitine O-palmitoyltransferase. This enzyme resides in the mitochondrial outer membrane. While this reaction takes place, the palmitoylcarnitine is moved into the mitochondrial intermembrane space. Following the reaction, the newly synthesized acylcarnitine is transported into the mitochondrial matrix by a mitochondrial carnitine/acylcarnitine carrier protein found in the mitochondrial inner membrane. Once in the matrix, palmitoylcarnitine can react with the carnitine O-palmitoyltransferase 2 enzyme found in the mitochondrial inner membrane to once again form palmitoyl-CoA and L-carnitine. Palmitoyl-CoA then enters into the mitochondrial beta-oxidation pathway to form aceytl-CoA. Acetyl-CoA can go on to enter the TCA cycle, or it can react with L-carnitine to form L-acetylcarnitine in a reaction catalyzed by Carnitine O-acetyltransferase. This reaction can occur in both directions, and L-acetylcarnitine and CoA can react to form acetyl-CoA and L-carnitine in certain circumstances. Finally, acetyl-CoA in the cytosol can be catalyzed by acetyl-CoA carboxylase 1 to form malonyl-CoA, which inhibits the action of carnitine O-palmitoyltransferase 1, thereby preventing palmitoylcarnitine from forming and thereby preventing it from being transported into the mitochondria. L-Palmitoylcarnitine has been also reported to change the activity of certain proteins and to stimulate the activity of caspases 3, 7, and 8. Interestingly, the level of this long-chain acylcarnitine has been shown to increase during apoptosis. Palmitoylcarnitine has also been reported to diminish the binding of phorbol esters (protein kinase C activators) and the autophosphorylation of the enzyme. Some of the physicochemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contributes to myocardial damage through alterations in membrane molecular dynamics. This is a mechanism through which could play an important role in ischemic injury (PMID: 2540838 , 15363641 , 8706815 ). Palmitoylcarnitine is characteristically elevated in late-onset carnitine palmitoyltransferase II deficiency (OMIM: 255110 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309172004422D          

 28 27  0  0  0  0            999 V2000
   -5.2885   -0.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5742   -0.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1424   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599    0.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2885    0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.0359    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -6.7212    0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563    1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9946   -0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9946   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805   -1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7089   -1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  1  21   1
M  END


  Mrv1652309172004422D          

 28 27  0  0  0  0            999 V2000
   -5.2885   -0.1993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5742   -0.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7126   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1424   -0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8563   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599    0.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2885    0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.0359    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -6.7212    0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    1.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563    1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9946   -0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9946   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805   -1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7089   -1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  1  21   1
M  END
> <DATABASE_ID>
MMDBc0000505

> <DATABASE_NAME>
MIME

> <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/p+1/t21-/m1/s1

> <INCHI_KEY>
XOMRRQXKHMYMOC-OAQYLSRUSA-O

> <FORMULA>
C23H46NO4

> <MOLECULAR_WEIGHT>
400.623

> <EXACT_MASS>
400.342135385

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.67963430941978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-carboxy-2-(hexadecanoyloxy)propyl]trimethylazanium

> <JCHEM_LOGP>
2.033547854194921

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022335

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
126.23959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+)-palmitoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0      -9.872  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.538  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.205  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.872  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.538  -0.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.205  -1.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.872  -0.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.538  -1.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.794  -0.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.130  -1.144   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.463  -0.372   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.799  -1.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.132  -0.372   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.464  -1.144   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.797  -0.372   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.133  -1.144   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.466  -0.372   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.798  -1.144   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.205   1.167   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.872   1.167   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0     -11.205   1.934   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0     -12.546   1.163   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.205   3.474   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.798   2.854   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.190  -1.163   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.190  -2.702   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.857  -3.474   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -12.523  -3.474   0.000  0.00  0.00           O+0
CONECT    1    2   20   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

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	MeSH
C16 Carnitine	HMDB
L-Palmitoylcarnitine	HMDB
Acylcarnitine C16:0	HMDB
C16:0 Carnitine	HMDB

Molecular Formula

C₂₃H₄₆NO₄

Average Mass

400.623

Monoisotopic Mass

400.342135385

IUPAC Name

[(2R)-3-carboxy-2-(hexadecanoyloxy)propyl]trimethylazanium

Traditional Name

(+)-palmitoylcarnitine

CAS Registry Number

Not Available

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/p+1/t21-/m1/s1

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-O

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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.03	ChemAxon
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	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	20	ChemAxon
Refractivity	126.24 m³·mol⁻¹	ChemAxon
Polarizability	50.68 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-1000900000-109f35c9819eb5eed7b7	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-9d6bb14eddb4cfa8341a	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-87b1d0debe4e0cb7bd31	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0139500000-21c36c851939b94d4523	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0029600000-69ebe292c2ce42c8d810	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-197944fd1aa4ac44bdd2	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000613900-006582b143e5906e51cc	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0uxr-0000614900-14a5d773f652b71671fb	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0f6x-0139600000-b0528be9c13e412551af	2020-09-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2020-09-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2020-09-17	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria

Biospecimen Locations

Blood
Feces
Placenta
Saliva
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191978	Carnitine O-palmitoyltransferase 1, muscle isoform	Enzyme	Q92523	Homo sapiens
MMDBp0191979	Carnitine O-palmitoyltransferase 1, liver isoform	Enzyme	P50416	Homo sapiens
MMDBp0191981	Carnitine O-palmitoyltransferase 2, mitochondrial	Enzyme	P23786	Homo sapiens
MMDBp0191982	Carnitine O-palmitoyltransferase 1, brain isoform	Enzyme	Q8TCG5	Homo sapiens
MMDBp0192221	Long-chain-fatty-acid--CoA ligase 1	Unknown	P33121	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Decreased	Association	Human Blood	HMDB	16425363
Very long chain acyl-coa dehydrogenase deficiency	Increased	Association	Human Blood	HMDB	9034211
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity	Slight Increase	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	2	Human appendix biopsy; Human stool; Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4	Human feces; Human stool; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.097	0.006			uM	Adult (>18 years old)	Both	Celiac disease	HMDB	16425363
Human Blood	Detected and Quantified	1.909		1.012	2.233	uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	HMDB	9034211
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	12482618
Human Urine	Detected and Quantified	0.0022		0.0020	0.0030	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			0.01	0.06	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.01		0.01	0.03	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.01		0.01	0.07	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.06	0.04			uM	Children (1-13 years old)	Both	Normal	HMDB	24521011
Human Blood	Detected and Quantified	0.11	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Blood	Detected and Quantified	0.113	0.006			uM	Adult (>18 years old)	Both	Normal	HMDB	16425363
Human Blood	Detected and Quantified	0.12	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	0.15	0.17			uM	Children (1-13 years old)	Both	Normal	HMDB	24521011
Human Blood	Detected and Quantified	0.153		0.073	0.227	uM	Children (1-13 years old)	Both	Normal	HMDB	9034211
Human Feces	Detected and Quantified	0.22	0.07			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.36	0.27			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Urine	Detected and Quantified	0.0046	0.0018			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.096	0.032			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.101	0.026			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Urine	Detected and Quantified	0.006	0.0018			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Saliva	Detected and Quantified	0.034	0.012			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.050	0.180	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.050	0.180	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23384618
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000222

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021910

KNApSAcK ID

Not Available

Chemspider ID

146753

KEGG Compound ID

C02990

BioCyc ID

CPD-419

BiGG ID

Not Available

Wikipedia Link

Palmitoylcarnitine

METLIN ID

Not Available

PubChem Compound

167760

PDB ID

Not Available

ChEBI ID

17490

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bhuiyan AK, Jackson S, Turnbull DM, Aynsley-Green A, Leonard JV, Bartlett K: The measurement of carnitine and acyl-carnitines: application to the investigation of patients with suspected inherited disorders of mitochondrial fatty acid oxidation. Clin Chim Acta. 1992 May 15;207(3):185-204. doi: 10.1016/0009-8981(92)90118-a. [PubMed:1327583 ]
Watanabe H, Kobayashi A, Hayashi H, Yamazaki N: Effects of long-chain acyl carnitine on membrane fluidity of human erythrocytes. Biochim Biophys Acta. 1989 Apr 28;980(3):315-8. doi: 10.1016/0005-2736(89)90318-0. [PubMed:2540838 ]
Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24. doi: 10.1006/abio.1994.1201. [PubMed:8074302 ]
Poorthuis BJ, Jille-Vlckova T, Onkenhout W: Determination of acylcarnitines in urine of patients with inborn errors of metabolism using high-performance liquid chromatography after derivatization with 4'-bromophenacylbromide. Clin Chim Acta. 1993 Jul 16;216(1-2):53-61. doi: 10.1016/0009-8981(93)90138-t. [PubMed:8222273 ]
Goni FM, Requero MA, Alonso A: Palmitoylcarnitine, a surface-active metabolite. FEBS Lett. 1996 Jul 15;390(1):1-5. doi: 10.1016/0014-5793(96)00603-5. [PubMed:8706815 ]
Wasant P, Matsumoto I, Naylor E, Liammongkolkul S: Mitochondrial fatty acid oxidation disorders in Thai infants: a report of 3 cases. J Med Assoc Thai. 2002 Aug;85 Suppl 2:S710-9. [PubMed:12403251 ]
Mueller P, Schulze A, Schindler I, Ethofer T, Buehrdel P, Ceglarek U: Validation of an ESI-MS/MS screening method for acylcarnitine profiling in urine specimens of neonates, children, adolescents and adults. Clin Chim Acta. 2003 Jan;327(1-2):47-57. doi: 10.1016/s0009-8981(02)00327-3. [PubMed:12482618 ]
Moder M, Kiessling A, Loster H, Bruggemann L: The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: a new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem. 2003 Jan;375(2):200-10. doi: 10.1007/s00216-002-1654-7. Epub 2003 Jan 4. [PubMed:12560963 ]
Young SP, Matern D, Gregersen N, Stevens RD, Bali D, Liu HM, Koeberl DD, Millington DS: A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 2003 Nov;337(1-2):103-13. doi: 10.1016/j.cccn.2003.07.006. [PubMed:14568186 ]
Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. doi: 10.1016/j.mam.2004.06.001. [PubMed:15363641 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Palmitoylcarnitine (MMDBc0000505)

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