Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:47:32 UTC
Update Date2022-10-24 19:44:17 UTC
HMDB IDHMDB0240775
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-(11-Carboxyundecanoyl)carnitine
DescriptionO-(11-Carboxyundecanoyl)carnitine is an acylcarnitine. More specifically, it is an dodecanedioic 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 (PMID: 35710135 ), 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. O-(11-Carboxyundecanoyl)carnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine O-(11-Carboxyundecanoyl)carnitine 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. 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 ). 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 (PMID: 35710135 ).
Structure
Data?1614147980
Synonyms
ValueSource
3-[(11-Carboxyundecanoyl)oxy]-4-(trimethylammonio)butanoateChEBI
3-[(11-Carboxyundecanoyl)oxy]-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC19H35NO6
Average Molecular Weight373.49
Monoisotopic Molecular Weight373.246437851
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C19H35NO6/c1-20(2,3)15-16(14-18(23)24)26-19(25)13-11-9-7-5-4-6-8-10-12-17(21)22/h16H,4-15H2,1-3H3,(H-,21,22,23,24)
InChI KeyULLMWXPSQSZINF-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Tricarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+176.14630932474
DeepCCS[M-H]-173.78830932474
DeepCCS[M-2H]-206.67230932474
DeepCCS[M+Na]+182.23930932474
AllCCS[M+H]+199.632859911
AllCCS[M+H-H2O]+197.432859911
AllCCS[M+NH4]+201.632859911
AllCCS[M+Na]+202.132859911
AllCCS[M-H]-198.732859911
AllCCS[M+Na-2H]-199.932859911
AllCCS[M+HCOO]-201.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-(11-Carboxyundecanoyl)carnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCC(O)=O3869.0Standard polar33892256
O-(11-Carboxyundecanoyl)carnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCC(O)=O2181.4Standard non polar33892256
O-(11-Carboxyundecanoyl)carnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCC(O)=O2585.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
O-(11-Carboxyundecanoyl)carnitine,1TMS,isomer #1C[N+](C)(C)CC(CC(=O)[O-])OC(=O)CCCCCCCCCCC(=O)O[Si](C)(C)C2663.6Semi standard non polar33892256
O-(11-Carboxyundecanoyl)carnitine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C2907.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-(11-Carboxyundecanoyl)carnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-(11-Carboxyundecanoyl)carnitine 10V, Positive-QTOFsplash10-00di-0009000000-140fe2cedd0f1f7f37a42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-(11-Carboxyundecanoyl)carnitine 20V, Positive-QTOFsplash10-0079-9005000000-4e34f9893708ffd26ec12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-(11-Carboxyundecanoyl)carnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71464543
PDB IDNot Available
ChEBI ID73064
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
  3. 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 ]
  4. 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 ]
  5. Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]