Cardiolipin

Identification

Name
Cardiolipin
Accession Number
DB03429  (EXPT00874)
Type
Small Molecule
Groups
Experimental
Description

Cardiolipin (bisphosphatidyl glycerol) is an important component of the inner mitochondrial membrane, where it constitutes about 20% of the total lipid. It is typically present in metabolically active cells of the heart and skeletal muscle, in the membranes of their mitochondria, mostly in the inner membrane, and consists roughly 20% of its lipids. It has also been observed in certain bacterial membranes. It serves as an insulator and stabilizes the activity of protein complexes important to the electron transport chain. It also "glues" them together. Cardiolipin is a "double" phospholipid because it has four fatty acid tails, instead of the usual two. [Wikipedia]

Structure
Thumb
Synonyms
  • CDL
  • Diphosphatidyl Glycerol
  • Diphosphatidylglycerol
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 1466.0585
Monoisotopic: 1465.097426654
Chemical Formula
C81H158O17P2
InChI Key
XVTUQDWPJJBEHJ-KZCWQMDCSA-N
InChI
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
IUPAC Name
[(2R)-2,3-bis(octadecanoyloxy)propoxy][3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[[email protected]](CO[[email protected]@](O)(=O)OCC(O)CO[[email protected]](O)(=O)OC[[email protected]@H](COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UADP/ATP translocase 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Moghis Ahmad, Murali Ukkalam, Imran Ahmad, "Cardiolipin molecules and methods of synthesis." U.S. Patent US20050266068, issued December 01, 2005.

US20050266068
General References
Not Available
External Links
Human Metabolome Database
HMDB56960
KEGG Compound
C05980
PubChem Compound
449005
PubChem Substance
46507093
ChemSpider
395642
ChEBI
62861
HET
CDL

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.62e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count86ChemAxon
Refractivity406.91 m3·mol-1ChemAxon
Polarizability184.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5109
Blood Brain Barrier+0.911
Caco-2 permeable-0.6129
P-glycoprotein substrateNon-substrate0.5122
P-glycoprotein inhibitor INon-inhibitor0.7392
P-glycoprotein inhibitor IINon-inhibitor0.6938
Renal organic cation transporterNon-inhibitor0.9471
CYP450 2C9 substrateNon-substrate0.8979
CYP450 2D6 substrateNon-substrate0.8451
CYP450 3A4 substrateNon-substrate0.5593
CYP450 1A2 substrateNon-inhibitor0.8687
CYP450 2C9 inhibitorNon-inhibitor0.8828
CYP450 2D6 inhibitorNon-inhibitor0.9152
CYP450 2C19 inhibitorNon-inhibitor0.8453
CYP450 3A4 inhibitorNon-inhibitor0.8316
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9706
Ames testNon AMES toxic0.832
CarcinogenicityNon-carcinogens0.5764
BiodegradationNot ready biodegradable0.7275
Rat acute toxicity1.7151 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9103
hERG inhibition (predictor II)Non-inhibitor0.7033
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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[[email protected]@H](CO[R1])O[R2])COP(O)(=O)OC[[email protected]@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphoglycerophosphoglycerols
Direct Parent
Cardiolipins
Alternative Parents
Tetracarboxylic acids and derivatives / Fatty acid esters / Dialkyl phosphates / Secondary alcohols / Carboxylic acid esters / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
cardiolipin (CHEBI:62861)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Adenine transmembrane transporter activity
Specific Function
Catalyzes the exchange of cytoplasmic ADP with mitochondrial ATP across the mitochondrial inner membrane.
Gene Name
SLC25A4
Uniprot ID
P12235
Uniprot Name
ADP/ATP translocase 1
Molecular Weight
33064.265 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:28