Showing metabocard for CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0010269)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:02:52 UTC
Update Date2020-05-11 19:10:19 UTC
BMDB IDBMDB0010269
Secondary Accession Numbers
  • BMDB10269
Metabolite Identification
Common NameCL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
DescriptionCL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), also known as Cl(20:4(5z,8z,11z,14z)/18:2(9z,12z)/18:2(9z,12z)/18:2(9z,12z)) or Cl(20:4(5z,8z,11z,14z)/18:2(9z,12z)/18:2(9z,12z)/18:2(9z,12z)), 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. Thus, CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1'-[1-Arachidonoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(20:4/18:2/18:2/18:2)HMDB
Cardiolipin(20:4N6/18:2N6/18:2N6/18:2N6)HMDB
Cardiolipin(20:4W6/18:2W6/18:2W6/18:2W6)HMDB
Cardiolipin(74:10)HMDB
Cardiolipins(20:4/18:2/18:2/18:2)HMDB
Cardiolipins(20:4N6/18:2N6/18:2N6/18:2N6)HMDB
Cardiolipins(20:4W6/18:2W6/18:2W6/18:2W6)HMDB
Cardiolipins(74:10)HMDB
CL(1'-[20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])HMDB
CL(20:4/18:2/18:2/18:2)HMDB
CL(20:4N6/18:2N6/18:2N6/18:2N6)HMDB
CL(20:4W6/18:2W6/18:2W6/18:2W6)HMDB
CL(74:10)HMDB
1'-[1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC83H142O17P2
Average Molecular Weight1473.9529
Monoisotopic Molecular Weight1472.972226142
IUPAC Name[3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-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-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C83H142O17P2/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/h21-28,33-37,39-42,44,52,56,77-79,84H,5-20,29-32,38,43,45-51,53-55,57-76H2,1-4H3,(H,89,90)(H,91,92)/b25-21-,26-22-,27-23-,28-24-,37-33-,39-34-,40-35-,41-36-,44-42-,56-52-/t77-,78-,79-/m1/s1
InChI KeySYNXSZYAORKNPA-ONLKWBODSA-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
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
logP9.19ALOGPS
logP24.54ChemAxon
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 Count78ChemAxon
Refractivity427.28 m³·mol⁻¹ChemAxon
Polarizability172.74 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-0011000900-4991b3f13be3df7cdd86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011310900-3672b2513befe43d94a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v2i-0066910100-b30fefd80e9f5b6d6f02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07bf-0983712322-5bb5977bafa4162a6fe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0393302131-b59279117a491b7ae7a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-1079412301-2c0a64467d5bdd944f9eView 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 IDHMDB0010269
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027421
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480403
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available