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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-09 08:21:14 UTC
Update Date2022-11-30 19:11:33 UTC
HMDB IDHMDB0058863
Secondary Accession Numbers
  • HMDB58863
Metabolite Identification
Common NameCL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))
DescriptionCL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called 'double' phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol 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. CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) contains one chain of (9Z,12Z-octadecadienoyl) at the C1 position, two chains of (5Z,8Z,11Z,14Z-eicosatetraenoyl) at the C2 and C3 positions, one chain of (9Z-octadecenoyl) at the C4 position fatty acids. Cardiolipins are known to be present in all mammalian cells, especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP-DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID: 16442164 ). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID: 16442164 ). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238 ).
Structure
Data?1563865846
Synonyms
ValueSource
CL(18:2/20:4/20:4/20:4)HMDB
Cardiolipin(78:14)HMDB
1'-[1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phospho],3'-[1,2-diarachidonoyl-rac-glycero-3-phospho]-glycerolHMDB
CL(1'-[18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)],3'-[20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)])HMDB
CL(78:14)HMDB
Cardiolipin(18:2/20:4/20:4/20:4)HMDB
1'-[1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho],3'-[1,2-di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))Lipid Annotator
Chemical FormulaC85H144O17P2
Average Molecular Weight1500.018
Monoisotopic Molecular Weight1498.987877173
IUPAC Name[(2R)-2-hydroxy-3-({hydroxy[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name(2R)-2-hydroxy-3-{[hydroxy((2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxy((2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)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
InChI Identifier
InChI=1S/C85H144O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)77-99-103(91,92)97-73-79(86)74-98-104(93,94)100-78-81(75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3)102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2/h21-23,25-27,33-38,41-44,46,48,54,56,58,60,79-81,86H,5-20,24,28-32,39-40,45,47,49-53,55,57,59,61-78H2,1-4H3,(H,91,92)(H,93,94)/b25-21-,26-22-,27-23-,37-33-,38-34-,41-35-,42-36-,46-43-,48-44-,58-54-,60-56-/t79-,80-,81-/m1/s1
InChI KeyUTFPCYFMSNTSMW-VCHWRDFISA-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
Water Solubility8.0e-05 g/LALOGPS
logP9.21ALOGPS
logP25.07ChemAxon
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 Count79ChemAxon
Refractivity437.6 m³·mol⁻¹ChemAxon
Polarizability176.15 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]+396.28430932474
DeepCCS[M-H]-393.48730932474
DeepCCS[M-2H]-428.44330932474
DeepCCS[M+Na]+403.46630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 10V, Negative-QTOFsplash10-0002-0031000900-7fcda92ec280693d27452017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 20V, Negative-QTOFsplash10-00kb-0031401900-3fe88cd5367d3e9e9caf2017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 40V, Negative-QTOFsplash10-0ge9-0084900000-81c1a3e344b647825d012017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 10V, Positive-QTOFsplash10-05r1-0090201201-1fa23ecdebeb6f51d9382017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 20V, Positive-QTOFsplash10-00mk-0091101111-7ff1888f18ddcad049252017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) 40V, Positive-QTOFsplash10-004s-0094315501-d38c23b4f823793979642017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB033869
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound118702971
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. Schlame M, Ren M, Xu Y, Greenberg ML, Haller I: Molecular symmetry in mitochondrial cardiolipins. Chem Phys Lipids. 2005 Dec;138(1-2):38-49. Epub 2005 Sep 7. [PubMed:16226238 ]
  2. Schlame M, Ren M: Barth syndrome, a human disorder of cardiolipin metabolism. FEBS Lett. 2006 Oct 9;580(23):5450-5. Epub 2006 Jul 17. [PubMed:16973164 ]
  3. Hauff KD, Hatch GM: Cardiolipin metabolism and Barth Syndrome. Prog Lipid Res. 2006 Mar;45(2):91-101. Epub 2006 Jan 18. [PubMed:16442164 ]