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Record Information
Version5.0
StatusPredicted
Creation Date2021-03-31 20:00:08 UTC
Update Date2022-10-24 19:45:31 UTC
HMDB IDHMDB0241878
Secondary Accession NumbersNone
Metabolite Identification
Common Name(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine
Description(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine is an acylcarnitine. More specifically, it is an (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic 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. (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 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 (PMID: 35710135 ).
Structure
Data?1622217433
SynonymsNot Available
Chemical FormulaC27H43NO6
Average Molecular Weight477.642
Monoisotopic Molecular Weight477.309038109
IUPAC Name3-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}oxy)-4-(trimethylazaniumyl)butanoate
Traditional Name3-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}oxy)-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)C(=O)CC1
InChI Identifier
InChI=1S/C27H43NO6/c1-5-6-9-12-22(29)17-15-21-16-18-25(30)24(21)13-10-7-8-11-14-27(33)34-23(19-26(31)32)20-28(2,3)4/h7,10,15,17,22-23,29H,5-6,8-9,11-14,16,18-20H2,1-4H3
InChI KeyFESCBWXOKTZVCP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Acyl-carnitine
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • 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
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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-0.038ChemAxon
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.73 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity158.6 m³·mol⁻¹ChemAxon
Polarizability54.73 ųChemAxon
Number of Rings1ChemAxon
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]+221.20530932474
DeepCCS[M-H]-217.94530932474
DeepCCS[M-2H]-253.11330932474
DeepCCS[M+Na]+229.27930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitineCCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)C(=O)CC14538.7Standard polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitineCCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)C(=O)CC12970.6Standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitineCCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)C(=O)CC13423.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,1TMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(=O)CC1)O[Si](C)(C)C3464.5Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,1TMS,isomer #2CCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C)=CC13444.0Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C3464.1Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C3278.4Standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C3948.1Standard polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,1TBDMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(=O)CC1)O[Si](C)(C)C(C)(C)C3688.4Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,1TBDMS,isomer #2CCCCCC(O)C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC13675.4Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TBDMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3916.7Semi standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TBDMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3536.7Standard non polar33892256
(5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine,2TBDMS,isomer #1CCCCCC(C=CC1=C(CC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C3972.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 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 - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 10V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 20V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 40V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 10V, Positive-QTOFsplash10-004i-0000900000-8ae7d1c9e70ef8760b7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 20V, Positive-QTOFsplash10-002r-9000500000-5be8a14bbbec9b7fd2612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E,3R)-3-Hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]