Showing metabocard for CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0010266)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:02:48 UTC
Update Date2020-05-11 19:10:16 UTC
BMDB IDBMDB0010266
Secondary Accession Numbers
  • BMDB10266
Metabolite Identification
Common NameCL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
DescriptionCL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) 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(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) contains one chain of (8Z,11Z,14Z-eicosatrienoyl) at the C1 position, three chains of (9Z,12Z-octadecadienoyl) at the C2, C3 and C4 positions 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1'-[1-Homo-g-linolenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolHMDB
1'-[1-Homo-gamma-linolenoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(20:3/18:2/18:2/18:2)HMDB
Cardiolipin(20:3N6/18:2N6/18:2N6/18:2N6)HMDB
Cardiolipin(20:3W6/18:2W6/18:2W6/18:2W6)HMDB
Cardiolipin(74:9)HMDB
Cardiolipins(20:3/18:2/18:2/18:2)HMDB
Cardiolipins(20:3N6/18:2N6/18:2N6/18:2N6)HMDB
Cardiolipins(20:3W6/18:2W6/18:2W6/18:2W6)HMDB
Cardiolipins(74:9)HMDB
CL(1'-[20:3(8Z,11Z,14Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])HMDB
CL(20:3/18:2/18:2/18:2)HMDB
CL(20:3N6/18:2N6/18:2N6/18:2N6)HMDB
CL(20:3W6/18:2W6/18:2W6/18:2W6)HMDB
CL(74:9)HMDB
1'-[1-(8Z,11Z,14Z-Eicosatrienoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC83H144O17P2
Average Molecular Weight1475.9688
Monoisotopic Molecular Weight1474.987876206
IUPAC Name[3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic 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)CCCCCCC\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C83H144O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h21-28,33-37,39-42,44,77-79,84H,5-20,29-32,38,43,45-76H2,1-4H3,(H,89,90)(H,91,92)/b25-21-,26-22-,27-23-,28-24-,37-33-,39-34-,40-35-,41-36-,44-42-/t77-,78-,79-/m1/s1
InChI KeyVFLUBNWAFVUCBP-LPUPPDTPSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Inner mitochondrial membrane
  • Intracellular membrane
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.24ALOGPS
logP24.9ChemAxon
logS-7.3ALOGPS
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
Refractivity426.16 m³·mol⁻¹ChemAxon
Polarizability173.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0011000900-ff3c44e77593dece7f13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011310900-8cb0109db275cfadf387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0atc-0066910100-a19bc0a120c447cc0855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07bb-0983712322-e163e87ede11e162726bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0393302131-541731b215c022fcb14eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1069412311-890adcd5d745f403be4fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Inner mitochondrial membrane
  • Intracellular membrane
  • Membrane
  • Mitochondria
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010266
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027418
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480400
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available