Showing metabocard for CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (BMDB0010312)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:04:09 UTC
Update Date2020-05-11 19:10:55 UTC
BMDB IDBMDB0010312
Secondary Accession Numbers
  • BMDB10312
Metabolite Identification
Common NameCL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))
DescriptionCL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), also known as Cl(22:6(4z,7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)/18:2(9z,12z)/18:2(9z,12z)) or Cl(22:6(4z,7z,10z,13z,16z,19z)/22:6(4z,7z,10z,13z,16z,19z)/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. CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) through the action of the enzyme cardiolipin synthase. In cattle, CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1'-[1,2-Didocosahexaenoyl-rac-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(22:6/22:6/18:2/18:2)HMDB
Cardiolipin(22:6N3/22:6N3/18:2N6/18:2N6)HMDB
Cardiolipin(22:6W3/22:6W3/18:2W6/18:2W6)HMDB
Cardiolipin(80:16)HMDB
Cardiolipins(22:6/22:6/18:2/18:2)HMDB
Cardiolipins(22:6N3/22:6N3/18:2N6/18:2N6)HMDB
Cardiolipins(22:6W3/22:6W3/18:2W6/18:2W6)HMDB
Cardiolipins(80:16)HMDB
CL(1'-[22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])HMDB
CL(22:6/22:6/18:2/18:2)HMDB
CL(22:6N3/22:6N3/18:2N6/18:2N6)HMDB
CL(22:6W3/22:6W3/18:2W6/18:2W6)HMDB
CL(80:16)HMDB
1'-[1,2-Di(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-rac-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))Lipid Annotator
Chemical FormulaC89H142O17P2
Average Molecular Weight1546.0171
Monoisotopic Molecular Weight1544.972226142
IUPAC Name[(2R)-2,3-bis[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]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[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C89H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-41-43-47-50-54-58-62-66-70-74-87(92)100-80-85(106-89(94)76-72-68-64-60-56-52-48-44-42-40-38-34-30-26-22-18-14-10-6-2)82-104-108(97,98)102-78-83(90)77-101-107(95,96)103-81-84(105-88(93)75-71-67-63-59-55-51-46-36-32-28-24-20-16-12-8-4)79-99-86(91)73-69-65-61-57-53-49-45-35-31-27-23-19-15-11-7-3/h9-10,13-14,21-28,33-38,41-46,50,52,54,56,62,64,66,68,83-85,90H,5-8,11-12,15-20,29-32,39-40,47-49,51,53,55,57-61,63,65,67,69-82H2,1-4H3,(H,95,96)(H,97,98)/b13-9-,14-10-,25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,43-41-,44-42-,45-35-,46-36-,54-50-,56-52-,66-62-,68-64-/t83-,84-,85-/m1/s1
InChI KeyKRRKIACLRUPTQQ-LNQVJMAWSA-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
logP8.83ALOGPS
logP25.04ChemAxon
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 Count78ChemAxon
Refractivity461.58 m³·mol⁻¹ChemAxon
Polarizability177.24 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-0011000900-b70f4c45d435d821ccd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0011301900-f4ab4f076728c8361b0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0066901100-bc74592a5a7a4e0df1aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02vr-0092051112-94ceca9ffada367cad1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02wi-0093031012-b9833869181e6e48f170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0069164231-24f946712168321aad72View 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 IDHMDB0010312
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027464
KNApSAcK IDNot Available
Chemspider ID35032050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480446
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available