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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-08-25 09:34:46 UTC
Update Date2022-11-30 19:24:22 UTC
HMDB IDHMDB0112060
Secondary Accession NumbersNone
Metabolite Identification
Common NameCL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionCL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) contains three chains of (5Z,8Z,11Z,14Z-eicosatetraenoyl) at the C1, C2 and C4 positions, one chain of (9Z,12Z-octadecadienoyl) at the C3 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.
Structure
Data?1563873213
Synonyms
ValueSource
CL(20:4/20:4/18:2/18:2)Lipid Annotator, HMDB
Cardiolipin(20:4/20:4/18:2/18:2)Lipid Annotator, HMDB
Cardiolipin(76:12)Lipid Annotator, HMDB
1'-[1,2-diarachidonoyl-rac-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
CL(76:12)Lipid Annotator, HMDB
1'-[1,2-di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
CL(1'-[20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])Lipid Annotator, HMDB
Chemical FormulaC87H142O17P2
Average Molecular Weight1522.024
Monoisotopic Molecular Weight1520.972227108
IUPAC Name[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy((2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphoryl]oxy}propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h21-28,33-39,43-46,48-50,56-58,60-62,81-83,88H,5-20,29-32,40-42,47,51-55,59,63-80H2,1-4H3,(H,93,94)(H,95,96)/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,43-36-,48-44-,49-45-,50-46-,60-56-,61-57-,62-58-/t81-,82-,83-/m1/s1
InChI KeyMEFSWTNMBRIQIW-NBVOEOQYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphoglycerols
Direct ParentCardiolipins
Alternative Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
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
logP8.95ALOGPS
logP24.87ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count78ChemAxon
Refractivity450.15 m³·mol⁻¹ChemAxon
Polarizability178.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+384.45630932474
DeepCCS[M-H]-382.72730932474
DeepCCS[M-2H]-416.75830932474
DeepCCS[M+Na]+390.7830932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOFsplash10-0a4i-0011000900-924844265bda826128ff2017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOFsplash10-0a4i-0011301900-f3a88c732eb501d8f1b72017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOFsplash10-0v2i-0066901100-02cb861e0e9353d35cb42017-10-05Wishart 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 IDFDB083650
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. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Houtkooper RH, Vaz FM: Cardiolipin, the heart of mitochondrial metabolism. Cell Mol Life Sci. 2008 Aug;65(16):2493-506. doi: 10.1007/s00018-008-8030-5. [PubMed:18425414 ]
  3. Lopez-Lopez A, Lopez-Sabater MC, Campoy-Folgoso C, Rivero-Urgell M, Castellote-Bargallo AI: Fatty acid and sn-2 fatty acid composition in human milk from Granada (Spain) and in infant formulas. Eur J Clin Nutr. 2002 Dec;56(12):1242-54. [PubMed:12494309 ]
  4. Jenkins B, West JA, Koulman A: A review of odd-chain fatty acid metabolism and the role of pentadecanoic Acid (c15:0) and heptadecanoic Acid (c17:0) in health and disease. Molecules. 2015 Jan 30;20(2):2425-44. doi: 10.3390/molecules20022425. [PubMed:25647578 ]
  5. Kingsbury KJ, Morgan DM: The analysis of the fatty acids of normal human depot fat by gas-liquid chromatography. Biochem J. 1964 Jan;90(1):140-7. [PubMed:5832283 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  8. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  10. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  11. Schlame M, Ren M: The role of cardiolipin in the structural organization of mitochondrial membranes. Biochim Biophys Acta. 2009 Oct;1788(10):2080-3. doi: 10.1016/j.bbamem.2009.04.019. Epub 2009 May 4. [PubMed:19413994 ]
  12. Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. [PubMed:10799718 ]
  13. McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. [PubMed:12531542 ]
  14. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  15. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.