Showing metabocard for CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0010692)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:11:55 UTC
Update Date2020-05-20 23:00:23 UTC
BMDB IDBMDB0010692
Secondary Accession Numbers
  • BMDB10692
Metabolite Identification
Common NameCL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
DescriptionCL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), also known as 1,1',2,2'-tetra-(9Z,12Z)-octadecadienoyl cardiolipin or Cl(18:2(9z,12z)/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(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. CL(18:2(9Z,12Z)/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(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) exists in all living organisms, ranging from bacteria to humans. CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) through its interaction with the enzyme cardiolipin synthase. In cattle, CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1',2,2'-Tetra-(9Z,12Z)-octadecadienoyl cardiolipinHMDB
1',3'-Bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolHMDB
1'-[1,2-Dilinoleoyl-sn-glycero-3-phospho]-3'-[1,2-dilinoleoyl-sn-glycero-3-phospho]-glycerolHMDB
1'-[1,2-Dilinoleoyl-rac-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(18:2/18:2/18:2/18:2)HMDB
Cardiolipin(72:8)HMDB
CL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])HMDB
CL(18:2/18:2/18:2/18:2)HMDB
CL(72:8)HMDB
1'-[1,2-Di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC81H142O17P2
Average Molecular Weight1449.9315
Monoisotopic Molecular Weight1448.972226142
IUPAC Name[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy][3-({[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(3-{[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)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)CCCCCCC\C=C/C\C=C/CCCCC)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/C81H142O17P2/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/h21-28,33-40,75-77,82H,5-20,29-32,41-74H2,1-4H3,(H,87,88)(H,89,90)/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,40-36-/t76-,77-/m1/s1
InChI KeyLSHJMDWWJIYXEM-XGJIDDIWSA-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 Descriptors
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
logP9.17ALOGPS
logP24.37ChemAxon
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
Refractivity415.84 m³·mol⁻¹ChemAxon
Polarizability169.92 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, Negativesplash10-00di-0010000900-f2544b47dd9b8598c9daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010110900-e918e9c2029a0c211a9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0090710100-9ec168c7c560739a0fc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015a-0951821330-816149c704f40f9ba96eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02h4-0965524260-2b996c80cb613e1b0d64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059l-1569464650-5a201d528171241fa694View 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 IDHMDB0010692
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027842
KNApSAcK IDNot Available
Chemspider ID21403032
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283539
PDB IDNot Available
ChEBI ID84398
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available