Showing metabocard for CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) (BMDB0010226)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:01:43 UTC
Update Date2020-05-11 19:09:43 UTC
BMDB IDBMDB0010226
Secondary Accession Numbers
  • BMDB10226
Metabolite Identification
Common NameCL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))
DescriptionCL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)), also known as Cl(18:1(11z)/18:1(11z)/18:1(11z)/18:2(9z,12z)) or Cl(18:1(11z)/18:1(11z)/18:1(11z)/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(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(18:1(11Z)/18:1(11Z)) and CDP-DG(18:1(11Z)/18:2(9Z,12Z)) through its interaction with the enzyme cardiolipin synthase. In cattle, CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cardiolipin(72:4)Lipid Annotator, HMDB
CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))Lipid Annotator
CL(72:4)Lipid Annotator, HMDB
CL(1'-[18:1(11Z)/18:1(11Z)],3'-[18:1(11Z)/18:1(11Z)])Lipid Annotator, HMDB
1'-[1,2-divaccenoyl-rac-glycero-3-phospho],3'-[1,2-divaccenoyl-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
CL(18:1/18:1/18:1/18:1)Lipid Annotator, HMDB
1'-[1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho],3'-[1,2-di(11Z-octadecenoyl)-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
Cardiolipin(18:1/18:1/18:1/18:1)Lipid Annotator, HMDB
Chemical FormulaC81H148O17P2
Average Molecular Weight1455.9791
Monoisotopic Molecular Weight1455.019176334
IUPAC Name[3-({[(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(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)-3-[(11Z)-octadec-11-enoyloxy]-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)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C81H148O17P2/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/h23,25-30,32,35,39,75-77,82H,5-22,24,31,33-34,36-38,40-74H2,1-4H3,(H,87,88)(H,89,90)/b27-23-,29-25-,30-26-,32-28-,39-35-/t75-,76-,77-/m1/s1
InChI KeyDVHFBMSATQSWMK-FGMTZBBSSA-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
logP9.13ALOGPS
logP25.46ChemAxon
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 Count81ChemAxon
Refractivity412.49 m³·mol⁻¹ChemAxon
Polarizability174.81 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-ce1f39939b3154f4c072View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0030310900-85c9889c88d3507946caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017i-0090600000-6daf8322a0e279c28d78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0avu-0950602330-370dd1b1435b537673b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-0952304260-dd79e5fb49e4d976f1c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kif-2898527450-ccbce04961a8e2d6bff5View 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 IDHMDB0010226
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