MiMeDB: Showing metabocard for 9,12-Hexadecadienylcarnitine (MMDBc0033538)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:44 UTC

Update Date

2024-04-30 20:12:09 UTC

Metabolite ID

MMDBc0033538

Metabolite Identification

Common Name

9,12-Hexadecadienylcarnitine

Description

9,12-Hexadecadienoylcarnitine is an acylcarnitine. More specifically, it is an 9,12-hexadecadienoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. 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. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. 9,12-Hexadecadienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 9,12-hexadecadienoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223162D          

 28 27  0  0  1  0            999 V2000
    2.1730   -1.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461   -4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -5.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139   -5.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -6.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0439   -6.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234   -6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -7.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266   -6.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825   -6.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -7.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6298   -7.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2535   -7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0330   -7.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6567   -8.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4362   -7.7805    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.5007   -8.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7857   -6.4302    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.5959   -6.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9756   -6.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416   -5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  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  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  CHG  2  23  -1  25   1
M  END


  Mrv0541 02241223162D          

 28 27  0  0  1  0            999 V2000
    2.1730   -1.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816   -3.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461   -4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -5.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139   -5.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -6.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407   -6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0439   -6.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234   -6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -7.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266   -6.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825   -6.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -7.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6298   -7.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2535   -7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0330   -7.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6567   -8.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4362   -7.7805    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.5007   -8.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7857   -6.4302    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.5959   -6.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9756   -6.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9416   -5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  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  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  CHG  2  23  -1  25   1
M  END
> <DATABASE_ID>
MMDBc0033538

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC=CCC=CCCCCCCCC(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(24(2,3)4)19-20-22(25)26/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/t21-/m0/s1

> <INCHI_KEY>
AHZCIODFJPNPKS-NRFANRHFSA-N

> <FORMULA>
C23H41NO4

> <MOLECULAR_WEIGHT>
395.5759

> <EXACT_MASS>
395.303558805

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.487926808194096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-(hexadeca-9,12-dienoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
1.6357752801949204

> <ALOGPS_LOGS>
-7.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.17471681475821

> <JCHEM_PKA_STRONGEST_BASIC>
-7.185041591485152

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
139.24269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-(hexadeca-9,12-dienoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.056  -2.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.765  -4.442   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -4.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.019  -6.458   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -6.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.273  -8.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.437  -9.483   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.146 -10.995   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310 -12.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.765 -11.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.929 -12.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.384 -12.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.549 -13.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.004 -12.507   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.168 -13.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.623 -13.011   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.914 -11.499   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.787 -14.019   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.242 -13.515   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.407 -14.524   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.862 -14.019   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.026 -15.028   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      19.481 -14.524   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0      17.735 -16.540   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0      14.533 -12.003   0.000  0.00  0.00           N+1
HETATM   26  C   UNK     0      16.046 -12.294   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.021 -11.712   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.824 -10.491   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₄₁NO₄

Average Mass

395.5759

Monoisotopic Mass

395.303558805

IUPAC Name

(4S)-4-(hexadeca-9,12-dienoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

(4S)-4-(hexadeca-9,12-dienoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCCC=CCC=CCCCCCCCC(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C

InChI Identifier

InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(24(2,3)4)19-20-22(25)26/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/t21-/m0/s1

InChI Key

AHZCIODFJPNPKS-NRFANRHFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.6e-05 g/L	ALOGPS
logP	0.54	ALOGPS
logP	1.64	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-7.2	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	18	ChemAxon
Refractivity	139.24 m³·mol⁻¹	ChemAxon
Polarizability	47.49 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f92-1109000000-eb5b74c30982e98fcaff	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-3920000000-abf1ed22b7ded8c0b18d	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-5920000000-bfbfb7b5568842d2ad72	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-0059000000-3baa5346a9141b44eca5	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-0094000000-a1ef9031a46b0f6a0600	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc3-6290000000-19dd8a13b0880b16a400	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Activity	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	0.01				uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Urine	Detected and Quantified			0.0	0.01	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.0010		0.0005	0.0040	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.11	0.04			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Feces	Detected and Quantified	0.19	0.09			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Saliva	Detected and Quantified	0.011	0.002			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.0080	0.0250	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. doi: 10.1016/s1388-1981(02)00296-2. [PubMed:12385891 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 9,12-Hexadecadienylcarnitine (MMDBc0033538)

MOL for #<Metabolite:0x00007fca2d938dd0>

3D MOL for #<Metabolite:0x00007fca2d938dd0>

3D SDF for #<Metabolite:0x00007fca2d938dd0>

3D-SDF for #<Metabolite:0x00007fca2d938dd0>

PDB for #<Metabolite:0x00007fca2d938dd0>

3D PDB for #<Metabolite:0x00007fca2d938dd0>

SMILES for #<Metabolite:0x00007fca2d938dd0>

INCHI for #<Metabolite:0x00007fca2d938dd0>

Structure for #<Metabolite:0x00007fca2d938dd0>

3D Structure for #<Metabolite:0x00007fca2d938dd0>