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Human Metabolome Database Version 3.5

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Showing metabocard for CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z)) (HMDB10235)

Record Information
Version 3.5
Creation Date 2008-09-15 04:33:45 -0600
Update Date 2013-02-08 17:24:19 -0700
HMDB ID HMDB10235
Secondary Accession Numbers None
Metabolite Identification
Common Name CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))
Description CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z)) 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1'-[1-Linoleoyl-2-oleoyl-sn-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerol
  2. Cardiolipin(18:2/18:1/18:1/18:1)
  3. Cardiolipin(18:2n6/18:1n9/18:1n9/18:1n9)
  4. Cardiolipin(18:2w6/18:1w9/18:1w9/18:1w9)
  5. Cardiolipin(72:5)
  6. Cardiolipins(18:2/18:1/18:1/18:1)
  7. Cardiolipins(18:2n6/18:1n9/18:1n9/18:1n9)
  8. Cardiolipins(18:2w6/18:1w9/18:1w9/18:1w9)
  9. Cardiolipins(72:5)
  10. CL(1'-[18:2(9Z,12Z)/18:1(9Z)],3'-[18:1(9Z)/18:1(9Z)])
  11. CL(18:2/18:1/18:1/18:1)
  12. CL(18:2n6/18:1n9/18:1n9/18:1n9)
  13. CL(18:2w6/18:1w9/18:1w9/18:1w9)
  14. CL(72:5)
Chemical Formula C79H144O17P2
Average Molecular Weight 1427.926
Monoisotopic Molecular Weight 1426.987876206
IUPAC Name [(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy][2-hydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional IUPAC Name (2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy(2-hydroxy-3-{[hydroxy(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphoryl]oxy}propoxy)phosphinic acid
CAS Registry Number Not Available
SMILES [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier InChI=1S/C79H144O17P2/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/h22,26,28,32-38,73-75,80H,5-21,23-25,27,29-31,39-72H2,1-4H3,(H,85,86)(H,87,88)/b26-22-,32-28-,36-33-,37-34-,38-35-/t73?,74-,75-/m1/s1
InChI Key RQDYMPBDKOFJQR-RCMCYCAASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Cardiolipins
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • 1,2 Diacylglycerophosphoradylglycerol
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Cardiolipins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 7.220E-05 g/L ALOGPS
LogP 9.10 ALOGPS
LogP 24.57 ChemAxon
LogS -7.30 ALOGPS
pKa (strongest acidic) 1.59 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 236.95 A2 ChemAxon
Rotatable Bond Count 79 ChemAxon
Refractivity 403.29 ChemAxon
Polarizability 170.41 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027387
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10235 Link_out
Metagene Link HMDB10235 Link_out
METLIN ID Not Available
PubChem Compound 53480369 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Beta-2-glycoprotein 1
Reactions:
    Gene Name: APOH
    Uniprot ID: P02749 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cardiolipin synthase
    Reactions:
      Gene Name: CRLS1
      Uniprot ID: Q9UJA2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lysocardiolipin acyltransferase 1
      Reactions:
        Gene Name: LCLAT1
        Uniprot ID: Q6UWP7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA