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Record Information
Version5.0
StatusPredicted
Creation Date2021-03-31 19:32:41 UTC
Update Date2022-10-24 19:45:19 UTC
HMDB IDHMDB0241689
Secondary Accession NumbersNone
Metabolite Identification
Common Name(2E)-Hept-2-enedioylcarnitine
Description(2E)-hept-2-enedioylcarnitine is an acylcarnitine. More specifically, it is an (2E)-hept-2-enedioic 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. (2E)-hept-2-enedioylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine (2E)-hept-2-enedioylcarnitine 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?1621682869
Synonyms
ValueSource
3-[(6-Carboxyhex-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoic acidGenerator
Chemical FormulaC14H23NO6
Average Molecular Weight301.339
Monoisotopic Molecular Weight301.152537465
IUPAC Name3-[(6-carboxyhex-2-enoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name3-[(6-carboxyhex-2-enoyl)oxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
C[N+](C)(C)CC(CC([O-])=O)OC(=O)C=CCCCC(O)=O
InChI Identifier
InChI=1S/C14H23NO6/c1-15(2,3)10-11(9-13(18)19)21-14(20)8-6-4-5-7-12(16)17/h6,8,11H,4-5,7,9-10H2,1-3H3,(H-,16,17,18,19)
InChI KeyBNOLNUDQIWBQTP-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
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Quaternary ammonium 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
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP-3.1ChemAxon
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.73 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity98.43 m³·mol⁻¹ChemAxon
Polarizability31.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+170.41330932474
DeepCCS[M-H]-168.05530932474
DeepCCS[M-2H]-200.9430932474
DeepCCS[M+Na]+176.50630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2E)-Hept-2-enedioylcarnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)C=CCCCC(O)=O3519.5Standard polar33892256
(2E)-Hept-2-enedioylcarnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)C=CCCCC(O)=O1838.5Standard non polar33892256
(2E)-Hept-2-enedioylcarnitineC[N+](C)(C)CC(CC([O-])=O)OC(=O)C=CCCCC(O)=O2101.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2E)-Hept-2-enedioylcarnitine,1TMS,isomer #1C[N+](C)(C)CC(CC(=O)[O-])OC(=O)C=CCCCC(=O)O[Si](C)(C)C2150.2Semi standard non polar33892256
(2E)-Hept-2-enedioylcarnitine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC=CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C2396.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2E)-Hept-2-enedioylcarnitine 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 - (2E)-Hept-2-enedioylcarnitine 10V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-Hept-2-enedioylcarnitine 20V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-Hept-2-enedioylcarnitine 40V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-Hept-2-enedioylcarnitine 10V, Positive-QTOFsplash10-0udi-0009000000-efa45185d002602f15882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-Hept-2-enedioylcarnitine 20V, Positive-QTOFsplash10-0f79-9005000000-e9123d4e58f7d7a8d41c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2E)-Hept-2-enedioylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
  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. Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
  6. Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
  7. Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
  8. 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 ]