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Showing metabocard for 11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine (HMDB0241833)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-03-31 19:53:36 UTC
Update Date2022-10-24 19:45:28 UTC
HMDB IDHMDB0241833
Secondary Accession NumbersNone
Metabolite Identification
Common Name11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine
Description11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine is an acylcarnitine. More specifically, it is an 11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoic 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. 11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine is therefore classified as a very-long chain AC. As a very long-chain acylcarnitine 11-{3,4-dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine is generally formed in the cytoplasm from very long acyl groups synthesized by fatty acid synthases or obtained from the diet. Very-long-chain fatty acids are generally too long to be involved in mitochondrial beta-oxidation. As a result peroxisomes are the main organelle where very-long-chain fatty acids are metabolized and their acylcarnitines synthesized (PMID: 18793625 ). Altered levels of very long-chain acylcarnitines can serve as useful markers for inherited disorders of peroxisomal metabolism. 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?1621815703
MOLSDFPDBSMILESInChI

MOL for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

Not Available

3D MOL for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

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3D SDF for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

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3D-SDF for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

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PDB for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

Not Available

3D PDB for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

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SMILES for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

Not Available

INCHI for HMDB0241833 (11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitine)

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC29H49NO5
Average Molecular Weight491.713
Monoisotopic Molecular Weight491.361073682
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C29H49NO5/c1-7-8-15-18-26-23(2)24(3)27(35-26)19-16-13-11-9-10-12-14-17-20-29(33)34-25(21-28(31)32)22-30(4,5)6/h15,18,25H,7-14,16-17,19-22H2,1-6H3
InChI KeyZOKGJZKYKVENGW-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effect
Health effect
Disposition
Biological location
ProcessNot Available
Role
Biological roleIndustrial application
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, 2022.8.48 minutes32390414
Predicted by Siyang on May 30, 202225.2547 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.26 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3087.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid386.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid288.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid215.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid603.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1048.8 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 Acid1139.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)180.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid2686.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid750.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2767.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid615.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid588.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate217.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA163.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water9.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitineCCCC=CC1=C(C)C(C)=C(CCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)O13935.5Standard polar33892256
11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitineCCCC=CC1=C(C)C(C)=C(CCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)O12931.3Standard non polar33892256
11-{3,4-Dimethyl-5-[(1E)-pent-1-en-1-yl]furan-2-yl}undecanoylcarnitineCCCC=CC1=C(C)C(C)=C(CCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C)O13328.4Semi 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
  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. Duranti G, Boenzi S, Rizzo C, Rava L, Di Ciommo V, Carrozzo R, Meschini MC, Johnson DW, Dionisi-Vici C: Urine acylcarnitine analysis by ESI-MS/MS: a new tool for the diagnosis of peroxisomal biogenesis disorders. Clin Chim Acta. 2008 Dec;398(1-2):86-9. doi: 10.1016/j.cca.2008.08.018. Epub 2008 Aug 28. [PubMed:18793625 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]