Showing Compound Card for Cardiolipin (CDB000800)

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Record Information
Version1.0
Created at2020-03-30 17:43:37 UTC
Updated at2020-12-07 19:07:47 UTC
CannabisDB IDCDB000800
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCardiolipin
DescriptionCL(18:0/18:0/18:0/18:0) is a cardiolipin (CL). Cardiolipins are sometimes called 'double' phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol 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(18:0/18:0/18:0/18:0) contains four chains of octadecanoic acid at the C1, C2, C3 and C4 positions fatty acids. Cardiolipins are known to be present in all mammalian cells, especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP-DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID: 16442164 ). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID: 16442164 ). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238 ). This compound is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1'2,2'-Tetra-dodecanoyl cardiolipinChEBI
1,1'2,2'-Tetra-dodecanoylcardiolipinChEBI
1,1'2,2'-Tetrastearoyl cardiolipinChEBI
1,1'2,2'-TetrastearoylcardiolipinChEBI
Tetra-dodecanoyl cardiolipinChEBI
Tetra-dodecanoylcardiolipinChEBI
TetrastearoylcardiolipinChEBI
1'-[1,2-Distearoyl-rac-glycero-3-phospho],3'-[1,2-distearoyl-rac-glycero-3-phospho]-glycerolHMDB
Cardiolipin(18:0/18:0/18:0/18:0)HMDB
Cardiolipin(72:0)HMDB
CL(1'-[18:0/18:0],3'-[18:0/18:0])HMDB
CL(72:0)HMDB
CardiolipinsHMDB
DiphosphatidylglycerolsHMDB
1'-[1,2-Dioctadecanoyl-rac-glycero-3-phospho],3'-[1,2-dioctadecanoyl-rac-glycero-3-phospho]-glycerolHMDB
CardiolipinHMDB
CL(18:0/18:0/18:0/18:0)Lipid Annotator
Chemical FormulaC81H158O17P2
Average Molecular Weight1466.06
Monoisotopic Molecular Weight1465.0974
IUPAC Name[(2R)-2,3-bis(octadecanoyloxy)propoxy][3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional Namecardiolipin
CAS Registry NumberNot Available
SMILES
[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C81H158O17P2/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/h75-77,82H,5-74H2,1-4H3,(H,87,88)(H,89,90)/t76-,77-/m1/s1
InChI KeyXVTUQDWPJJBEHJ-KZCWQMDCSA-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 Parents
Substituents
  • Cardiolipin
  • Tetracarboxylic acid or derivatives
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

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Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.97ALOGPS
logP27.27ChemAxon
logS-7.4ALOGPS
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 Count86ChemAxon
Refractivity406.91 m³·mol⁻¹ChemAxon
Polarizability184.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0010000900-a9a34948633c72313d0b2017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0010110900-6c9bd2b809a3558c74e22017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0090710100-465dffdd45d2212f0c1f2017-10-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0951803530-a84e29415e3d5e6d53dc2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0532-0983607760-eb0caccb0b4f9d88afc72017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aov-1467428920-56dd8a6a948ebefa89ee2017-10-06View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0056960
DrugBank IDDB03429
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005367
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound449005
PDB IDNot Available
ChEBI ID62861
References
General References
  1. Hauff KD, Hatch GM: Cardiolipin metabolism and Barth Syndrome. Prog Lipid Res. 2006 Mar;45(2):91-101. doi: 10.1016/j.plipres.2005.12.001. Epub 2006 Jan 18. [PubMed:16442164 ]
  2. Schlame M, Ren M: Barth syndrome, a human disorder of cardiolipin metabolism. FEBS Lett. 2006 Oct 9;580(23):5450-5. doi: 10.1016/j.febslet.2006.07.022. Epub 2006 Jul 17. [PubMed:16973164 ]
  3. Schlame M, Ren M, Xu Y, Greenberg ML, Haller I: Molecular symmetry in mitochondrial cardiolipins. Chem Phys Lipids. 2005 Dec;138(1-2):38-49. doi: 10.1016/j.chemphyslip.2005.08.002. Epub 2005 Sep 7. [PubMed:16226238 ]