Record Information
Version1.0
Creation date2011-09-21 01:23:36 UTC
Update date2015-07-21 06:59:06 UTC
Primary IDFDB027382
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)
DescriptionCL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0) 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-Linoleoyl-2-vaccenoyl-sn-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(18:2/18:1/18:1/18:1)HMDB
Cardiolipin(18:2N6/18:1N7/18:1N9/18:1N9)HMDB
Cardiolipin(18:2W6/18:1W7/18:1W9/18:1W9)HMDB
Cardiolipin(72:5)HMDB
Cardiolipins(18:2/18:1/18:1/18:1)HMDB
Cardiolipins(18:2N6/18:1N7/18:1N9/18:1N9)HMDB
Cardiolipins(18:2W6/18:1W7/18:1W9/18:1W9)HMDB
Cardiolipins(72:5)HMDB
CL(1'-[18:2(9Z,12Z)/18:1(11Z)],3'-[18:1(9Z)/18:1(9Z)])HMDB
CL(18:2/18:1/18:1/18:1)HMDB
CL(18:2N6/18:1N7/18:1N9/18:1N9)HMDB
CL(18:2W6/18:1W7/18:1W9/18:1W9)HMDB
CL(72:5)HMDB
1'-[1-(9Z,12Z-Octadecadienoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho]-glycerolHMDB
CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)Lipid Annotator
1'-[1-Linoleoyl-2-vaccenoyl-sn-glycero-3-O],3'-[1,2-dioleoyl-rac-glycero-3-O]-glycerolHMDB
Predicted Properties
PropertyValueSource
Water Solubility7.3e-05 g/LALOGPS
logP9.07ALOGPS
logP24.93ChemAxon
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
Refractivity402.17 m³·mol⁻¹ChemAxon
Polarizability172.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC79H146O17P2
IUPAC name[3-({[(2R)-2-(hexadecanoyloxy)-3-(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid
InChI IdentifierInChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-43-47-51-55-59-63-76(81)89-69-74(95-78(83)65-61-57-53-49-45-39-32-28-24-20-16-12-8-4)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)70-90-77(82)64-60-56-52-48-44-41-37-34-30-26-22-18-14-10-6-2/h22,26-27,31,33-34,36-37,73-75,80H,5-21,23-25,28-30,32,35,38-72H2,1-4H3,(H,85,86)(H,87,88)/t73?,74-,75-/m1/s1
InChI KeyDFZYFBOIJNTFAC-LAPMJKMRSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC)OC(=O)CCCCCCCCCCCCCCC
Average Molecular Weight1429.9419
Monoisotopic Molecular Weight1429.00352627
Classification
ClassificationNot classified
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
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53480364
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10230
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