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Showing metabocard for (5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine (HMDB0241583)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-03-31 19:17:19 UTC
Update Date2022-10-24 19:45:12 UTC
HMDB IDHMDB0241583
Secondary Accession NumbersNone
Metabolite Identification
Common Name(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine
Description(5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoylcarnitine is an acylcarnitine. More specifically, it is an (5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic 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,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (5Z,8Z,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoylcarnitine 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?1621439573
MOLSDFPDBSMILESInChI

MOL for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

3D MOL for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

3D SDF for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

3D-SDF for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

PDB for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

3D PDB for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

SMILES for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available

INCHI for HMDB0241583 ((5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine)

Not Available
View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC27H47NO7
Average Molecular Weight497.673
Monoisotopic Molecular Weight497.335252857
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C27H47NO7/c1-5-6-12-15-22(29)18-19-25(31)24(30)16-13-10-8-7-9-11-14-17-27(34)35-23(20-26(32)33)21-28(2,3)4/h7,9-10,13,18-19,22-25,29-31H,5-6,8,11-12,14-17,20-21H2,1-4H3
InChI KeyFYSRHTXDKAIONW-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not AvailableNot Available
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 Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.5.94 minutes32390414
Predicted by Siyang on May 30, 202215.3406 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.43 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2482.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid177.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid210.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid180.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid200.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid643.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid489.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)651.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1526.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid538.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1846.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid382.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid422.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate367.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA131.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitineCCCCCC(O)C=CC(O)C(O)CC=CCC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C4023.6Standard polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitineCCCCCC(O)C=CC(O)C(O)CC=CCC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2758.6Standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitineCCCCCC(O)C=CC(O)C(O)CC=CCC=CCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3407.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TMS,isomer #1CCCCCC(C=CC(O)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3550.4Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TMS,isomer #2CCCCCC(O)C=CC(O[Si](C)(C)C)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C3541.6Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TMS,isomer #3CCCCCC(O)C=CC(O)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3545.9Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TMS,isomer #1CCCCCC(C=CC(O[Si](C)(C)C)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3491.5Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TMS,isomer #2CCCCCC(C=CC(O)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3491.9Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TMS,isomer #3CCCCCC(O)C=CC(O[Si](C)(C)C)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3521.1Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,3TMS,isomer #1CCCCCC(C=CC(O[Si](C)(C)C)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3436.0Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TBDMS,isomer #1CCCCCC(C=CC(O)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3770.9Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TBDMS,isomer #2CCCCCC(O)C=CC(O[Si](C)(C)C(C)(C)C)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C3766.0Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,1TBDMS,isomer #3CCCCCC(O)C=CC(O)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3768.5Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TBDMS,isomer #1CCCCCC(C=CC(O[Si](C)(C)C(C)(C)C)C(O)CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3955.0Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TBDMS,isomer #2CCCCCC(C=CC(O)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3951.1Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,2TBDMS,isomer #3CCCCCC(O)C=CC(O[Si](C)(C)C(C)(C)C)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3950.7Semi standard non polar33892256
(5Z,8Z,13E,15S)-11,12,15-Trihydroxyicosa-5,8,13-trienoylcarnitine,3TBDMS,isomer #1CCCCCC(C=CC(O[Si](C)(C)C(C)(C)C)C(CC=CCC=CCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4070.2Semi standard non polar33892256
Spectra
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
External LinksNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  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 ]