NAV

Tetrastearoyl cardiolipin

Identification

Generic Name
Tetrastearoyl cardiolipin
DrugBank Accession Number
DB03429
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 1466.0585
Monoisotopic: 1465.097426654
Chemical Formula
C81H158O17P2
Synonyms
  • 1,1'2,2'-tetra-dodecanoyl cardiolipin
  • 1,1'2,2'-tetra-dodecanoylcardiolipin
  • 1,1'2,2'-tetrastearoyl cardiolipin
  • 1,1'2,2'-tetrastearoylcardiolipin
  • tetra-dodecanoyl cardiolipin
  • tetra-dodecanoylcardiolipin
  • tetrastearoylcardiolipin

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UADP/ATP translocase 1Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@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
Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cardiolipin / Dialkyl phosphate / Fatty acid ester / Fatty acyl
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
cardiolipin (CHEBI:62861)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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[C@H](COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

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
Human Metabolome Database
HMDB0056960
KEGG Compound
C05980
PubChem Compound
449005
PubChem Substance
46507093
ChemSpider
395642
ChEBI
62861
PDBe Ligand
CDL
Wikipedia
Cardiolipin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

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Details1. ADP/ATP translocase 1
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52