Record Information
Version1.0
Creation date2011-09-21 01:23:33 UTC
Update date2020-04-06 23:43:41 UTC
Primary IDFDB027379
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))
DescriptionCL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)) is a cardiolipin (CL). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1'-[1,2-Dioleoyl-rac-glycero-3-O],3'-[1,2-dioleoyl-rac-glycero-3-O]-glycerolHMDB
CL(1'-[18:1(9Z)/18:1(9Z)],3'-[18:1(9Z)/18:1(9Z)])HMDB
Predicted Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP9.14ALOGPS
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
Polarizability178.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC81H148O17P2
IUPAC name[3-({[(2R)-2,3-bis(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-(octadec-9-enoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid
InChI IdentifierInChI=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/h23,27,33-40,75-77,82H,5-22,24-26,28-32,41-74H2,1-4H3,(H,87,88)(H,89,90)/t75?,76-,77-/m1/s1
InChI KeyHGIKPGJCIWRORL-GXYAQEMJSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC
Average Molecular Weight1455.9791
Monoisotopic Molecular Weight1455.019176334
Classification
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
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53480361
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10227
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cardiolipin synthaseCRLS1Q9UJA2
Beta-2-glycoprotein 1APOHP02749
Lysocardiolipin acyltransferase 1LCLAT1Q6UWP7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference