Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Tetrastearoyl cardiolipin
- DrugBank Accession Number
- DB03429
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Tetrastearoyl cardiolipin (DB03429)
- 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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Not Available
- Mechanism of action
Target Actions Organism UADP/ATP translocase 1 Not Available Humans - 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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Not Available
- Pathways
Pathway Category 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
- External Links
- 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
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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
Property Value Source Water Solubility 6.62e-05 mg/mL ALOGPS logP 8.97 ALOGPS logP 27.27 Chemaxon logS -7.4 ALOGPS pKa (Strongest Acidic) 1.59 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 236.95 Å2 Chemaxon Rotatable Bond Count 86 Chemaxon Refractivity 406.91 m3·mol-1 Chemaxon Polarizability 184.51 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5109 Blood Brain Barrier + 0.911 Caco-2 permeable - 0.6129 P-glycoprotein substrate Non-substrate 0.5122 P-glycoprotein inhibitor I Non-inhibitor 0.7392 P-glycoprotein inhibitor II Non-inhibitor 0.6938 Renal organic cation transporter Non-inhibitor 0.9471 CYP450 2C9 substrate Non-substrate 0.8979 CYP450 2D6 substrate Non-substrate 0.8451 CYP450 3A4 substrate Non-substrate 0.5593 CYP450 1A2 substrate Non-inhibitor 0.8687 CYP450 2C9 inhibitor Non-inhibitor 0.8828 CYP450 2D6 inhibitor Non-inhibitor 0.9152 CYP450 2C19 inhibitor Non-inhibitor 0.8453 CYP450 3A4 inhibitor Non-inhibitor 0.8316 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9706 Ames test Non AMES toxic 0.832 Carcinogenicity Non-carcinogens 0.5764 Biodegradation Not ready biodegradable 0.7275 Rat acute toxicity 1.7151 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9103 hERG inhibition (predictor II) Non-inhibitor 0.7033
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 383.6475 predictedDeepCCS 1.0 (2019) [M+H]+ 386.44495 predictedDeepCCS 1.0 (2019) [M+Na]+ 393.62698 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- ADP:ATP antiporter that mediates import of ADP into the mitochondrial matrix for ATP synthesis, and export of ATP out to fuel the cell (PubMed:21586654, PubMed:27693233). Cycles between the cytoplasmic-open state (c-state) and the matrix-open state (m-state): operates by the alternating access mechanism with a single substrate-binding site intermittently exposed to either the cytosolic (c-state) or matrix (m-state) side of the inner mitochondrial membrane (By similarity). In addition to its ADP:ATP antiporter activity, also involved in mitochondrial uncoupling and mitochondrial permeability transition pore (mPTP) activity (PubMed:31883789). Plays a role in mitochondrial uncoupling by acting as a proton transporter: proton transport uncouples the proton flows via the electron transport chain and ATP synthase to reduce the efficiency of ATP production and cause mitochondrial thermogenesis (By similarity). Proton transporter activity is inhibited by ADP:ATP antiporter activity, suggesting that SLC25A4/ANT1 acts as a master regulator of mitochondrial energy output by maintaining a delicate balance between ATP production (ADP:ATP antiporter activity) and thermogenesis (proton transporter activity) (By similarity). Proton transporter activity requires free fatty acids as cofactor, but does not transport it (By similarity). Also plays a key role in mPTP opening, a non-specific pore that enables free passage of the mitochondrial membranes to solutes of up to 1.5 kDa, and which contributes to cell death (PubMed:31883789). It is however unclear if SLC25A4/ANT1 constitutes a pore-forming component of mPTP or regulates it (By similarity). Acts as a regulator of mitophagy independently of ADP:ATP antiporter activity: promotes mitophagy via interaction with TIMM44, leading to inhibit the presequence translocase TIMM23, thereby promoting stabilization of PINK1 (By similarity)
- Specific Function
- Adenine transmembrane transporter activity
- Gene Name
- SLC25A4
- Uniprot ID
- P12235
- Uniprot Name
- ADP/ATP translocase 1
- Molecular Weight
- 33064.265 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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