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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:44 UTC
Update Date2021-04-12 19:31:41 UTC
HMDB IDHMDB0002250
Secondary Accession Numbers
  • HMDB0062713
  • HMDB02250
  • HMDB62713
Metabolite Identification
Common NameDodecanoylcarnitine
DescriptionDodecanoylcarnitine is an acylcarnitine. More specifically, it is an dodecanoic 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. Dodecanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine Dodecanoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. In particular Dodecanoylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211 ), Yin deficiency (PMID: 31909891 ), multiple acyl coenzyme A dehydrogenase deficiency (PMID: 30510944 ), CVD in type 2 diabetes Mellitus (PMID: 32431666 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with Celiac disease (PMID: 16425363 ), psoriasis (PMID: 28695330 ), intracerebral hemorrhage (PMID: 29265114 ), and pregnancy (PMID: 24704061 - in serum of pregnant women with fetus with CHD). Dodecanoylcarnitine is elevated in the urine of individuals with renal cell carcinoma (PMID: 29658093 ). Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). Dodecanoylcarnitine is also present in fatty acid oxidation disorders such as long-chain acyl CoA dehydrogenase deficiency, carnitine palmitoyltransferase I deficiency, and carnitine palmitoyltransferase II deficiency (PMID: 12828998 ). 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
Data?1614287406
Synonyms
ValueSource
(-)-LauroylcarnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoateChEBI
(R)-DodecanoylcarnitineChEBI
Dodecanoyl-L-carnitineChEBI
L-Carnitine dodecanoyl esterChEBI
Lauroyl-L(-)-carnitinChEBI
Lauroyl-L-carnitineChEBI
LauroylcarnitineChEBI
LaurylcarnitineChEBI
O-C12:0-L-CarnitineChEBI
O-Dodecanoyl-R-carnitineChEBI
(3R)-3-(Dodecanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
C12 CarnitineHMDB
L-LauroylcarnitineHMDB
Lauroyl-L(-)-carnitineHMDB
O-DodecanoylcarnitineHMDB
O-LauroylcarnitineHMDB
O-Lauroyl-L-carnitineHMDB
DodecanoylcarnitineHMDB
Chemical FormulaC19H38NO4
Average Molecular Weight344.515
Monoisotopic Molecular Weight344.279535128
IUPAC Name(3R)-3-(dodecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namelauroyl-L(-)-carnitin
CAS Registry Number25518-54-1
SMILES
CCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C19H37NO4/c1-5-6-7-8-9-10-11-12-13-14-19(23)24-17(15-18(21)22)16-20(2,3)4/h17H,5-16H2,1-4H3/p+1/t17-/m1/s1
InChI KeyFUJLYHJROOYKRA-QGZVFWFLSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.8e-05 g/LALOGPS
logP0.03ALOGPS
logP0.26ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity118.67 m³·mol⁻¹ChemAxon
Polarizability41.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9300000000-0cd49618a50984aad982Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-0900000000-1c57ff1372236d823d80Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-ef35ea7a4d61bac8cb20Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1 +/- 0.03 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.057-0.190 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.052 +/- 0.004 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.057-0.190 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.1(0.04) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.038 (0.005-0.069) uMChildren (1-13 years old)BothNormal details
FecesDetected and Quantified0.42 +/- 0.28 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.64 +/- 0.3 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.02 (0.01-0.04) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.03-0.25 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.07(0.03-0.14) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.07(0.04-0.28) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.032 +/- 0.002 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.15(0.07) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.045 (0.0197) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.0651 (0.0228) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.080 +/- 0.025 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.086 +/- 0.038 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.124 (0.090-0.162) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022928
KNApSAcK IDNot Available
Chemspider ID147288
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6573
PubChem Compound168381
PDB IDNot Available
ChEBI ID77086
Food Biomarker OntologyNot Available
VMH IDDDECCRN
MarkerDB IDMDB00000387
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. Epub 2003 Jan 4. [PubMed:12560963 ]
  2. Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72. [PubMed:12828998 ]
  3. Vianey-Saban C, Divry P, Brivet M, Nada M, Zabot MT, Mathieu M, Roe C: Mitochondrial very-long-chain acyl-coenzyme A dehydrogenase deficiency: clinical characteristics and diagnostic considerations in 30 patients. Clin Chim Acta. 1998 Jan 12;269(1):43-62. [PubMed:9498103 ]
  4. Morrow RJ, Rose ME: Isolation of acylcarnitines from urine: a comparison of methods and application to long-chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 1992 Oct 15;211(1-2):73-81. [PubMed:1468155 ]
  5. 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 ]
  6. 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 ]
  7. Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
  8. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
  9. Yi WJ, Chen J, Li ZB, Jiang TT, Bi DQ, Liu CM, Yang S, Hu YT, Gan L, Tu HH, Huang H, Li JC: Screening of potential biomarkers for Yin-deficiency-heat syndrome based on UHPLC-MS method and the mechanism of Zhibai Dihuang granule therapeutic effect. Anat Rec (Hoboken). 2020 Aug;303(8):2095-2108. doi: 10.1002/ar.24352. Epub 2020 Jan 7. [PubMed:31909891 ]
  10. Saral NY, Aksungar FB, Aktuglu-Zeybek C, Coskun J, Demirelce O, Serteser M: Glutaric acidemia type II patient with thalassemia minor and novel electron transfer flavoprotein-A gene mutations: A case report and review of literature. World J Clin Cases. 2018 Nov 26;6(14):786-790. doi: 10.12998/wjcc.v6.i14.786. [PubMed:30510944 ]
  11. Zhao S, Feng XF, Huang T, Luo HH, Chen JX, Zeng J, Gu M, Li J, Sun XY, Sun D, Yang X, Fang ZZ, Cao YF: The Association Between Acylcarnitine Metabolites and Cardiovascular Disease in Chinese Patients With Type 2 Diabetes Mellitus. Front Endocrinol (Lausanne). 2020 May 5;11:212. doi: 10.3389/fendo.2020.00212. eCollection 2020. [PubMed:32431666 ]
  12. Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
  13. Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
  14. Ottas A, Fishman D, Okas TL, Kingo K, Soomets U: The metabolic analysis of psoriasis identifies the associated metabolites while providing computational models for the monitoring of the disease. Arch Dermatol Res. 2017 Sep;309(7):519-528. doi: 10.1007/s00403-017-1760-1. Epub 2017 Jul 10. [PubMed:28695330 ]
  15. Zhang X, Li Y, Liang Y, Sun P, Wu X, Song J, Sun X, Hong M, Gao P, Deng D: Distinguishing Intracerebral Hemorrhage from Acute Cerebral Infarction through Metabolomics. Rev Invest Clin. 2017 Nov-Dec;69(6):319-328. doi: 10.24875/RIC.17002348. [PubMed:29265114 ]
  16. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
  17. Niziol J, Bonifay V, Ossolinski K, Ossolinski T, Ossolinska A, Sunner J, Beech I, Arendowski A, Ruman T: Metabolomic study of human tissue and urine in clear cell renal carcinoma by LC-HRMS and PLS-DA. Anal Bioanal Chem. 2018 Jun;410(16):3859-3869. doi: 10.1007/s00216-018-1059-x. Epub 2018 Apr 16. [PubMed:29658093 ]
  18. Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]