Showing metabocard for CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) (BMDB0010238)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:02:03 UTC
Update Date2020-05-11 19:09:53 UTC
BMDB IDBMDB0010238
Secondary Accession Numbers
  • BMDB10238
Metabolite Identification
Common NameCL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))
DescriptionCL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)), also known as Cl(18:2(9z,12z)/18:2(9z,12z)/18:1(11z)/18:1(11z)) or Cl(18:2(9z,12z)/18:2(9z,12z)/18:1(11z)/18:1(11z)), 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. CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/18:2(9Z,12Z)) and CDP-DG(18:1(11Z)/18:1(11Z)); which is mediated by the enzyme cardiolipin synthase. In cattle, CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cardiolipin(72:6)HMDB
CL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[18:1(11Z)/18:1(11Z)])HMDB
CL(72:6)HMDB
CL(18:2/18:2/18:1/18:1)HMDB
1'-[1,2-Dilinoleoyl-rac-glycero-3-phospho],3'-[1,2-divaccenoyl-rac-glycero-3-phospho]-glycerolHMDB
1'-[1,2-Di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho],3'-[1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(18:2/18:2/18:1/18:1)HMDB
Cardiolipin(18:2N6/18:2N6/18:1N7/18:1N7)HMDB
Cardiolipin(18:2W6/18:2W6/18:1W7/18:1W7)HMDB
Cardiolipins(18:2/18:2/18:1/18:1)HMDB
Cardiolipins(18:2N6/18:2N6/18:1N7/18:1N7)HMDB
Cardiolipins(18:2W6/18:2W6/18:1W7/18:1W7)HMDB
Cardiolipins(72:6)HMDB
CL(18:2N6/18:2N6/18:1N7/18:1N7)HMDB
CL(18:2W6/18:2W6/18:1W7/18:1W7)HMDB
1'-[1-Linoleoyl-2-oleoyl-sn-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(18:2/18:1/18:1/18:1)HMDB
Cardiolipin(18:2N6/18:1N9/18:1N9/18:1N9)HMDB
Cardiolipin(18:2W6/18:1W9/18:1W9/18:1W9)HMDB
Cardiolipin(72:5)HMDB
Cardiolipins(18:2/18:1/18:1/18:1)HMDB
Cardiolipins(18:2N6/18:1N9/18:1N9/18:1N9)HMDB
Cardiolipins(18:2W6/18:1W9/18:1W9/18:1W9)HMDB
Cardiolipins(72:5)HMDB
CL(1'-[18:2(9Z,12Z)/18:1(9Z)],3'-[18:1(9Z)/18:1(9Z)])HMDB
CL(18:2/18:1/18:1/18:1)HMDB
CL(18:2N6/18:1N9/18:1N9/18:1N9)HMDB
CL(18:2W6/18:1W9/18:1W9/18:1W9)HMDB
CL(72:5)HMDB
1'-[1-(9Z,12Z-Octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))Lipid Annotator
Chemical FormulaC81H146O17P2
Average Molecular Weight1453.9633
Monoisotopic Molecular Weight1453.00352627
IUPAC Name[3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid
Traditional Name3-{[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C81H146O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h21,23,25-28,30,32-33,35,37,39,75-77,82H,5-20,22,24,29,31,34,36,38,40-74H2,1-4H3,(H,87,88)(H,89,90)/b25-21-,27-23-,30-26-,32-28-,37-33-,39-35-/t75-,76+,77+/m0/s1
InChI KeyXJRSYDYSOAUFKR-WVNIQCPVSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP9.16ALOGPS
logP25.1ChemAxon
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 Count80ChemAxon
Refractivity413.61 m³·mol⁻¹ChemAxon
Polarizability173.89 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, Negativesplash10-004i-0030000900-b2ac7e4a8d7707ed80a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0030310900-7d57f6e5dd65967e6880View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017i-0090600000-ba0ce4a46dbcc844d76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe3-0940603340-cac408ea9e5f115cdd67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0942304260-9c2d04916f1de25af7d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-1977536880-43437eddf1777ee2a1f2View 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 IDHMDB0010238
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available