| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-03-17 20:10:44 UTC |
|---|
| Updated at | 2022-03-17 20:10:44 UTC |
|---|
| NP-MRD ID | NP0046657 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Cardiolipin |
|---|
| Description | CL(18:0/18:0/18:0/18:0), Also known as tetra-dodecanoylcardiolipin or cardiolipins, 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. Thus, CL(18:0/18:0/18:0/18:0) Is considered to be a glycerophosphoglycerophosphoglycerol lipid molecule. A CL(18:0/18:0/18:0/18:0) Derivative in which all four of the phosphatidyl acyl groups are specified as stearoyl (octadecanoyl). CL(18:0/18:0/18:0/18:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. CL(18:0/18:0/18:0/18:0) Exists in all living species, ranging from bacteria to humans. Outside of the human body, CL(18:0/18:0/18:0/18:0) Is found, on average, in the highest concentration within apples. CL(18:0/18:0/18:0/18:0) Has also been detected, but not quantified in, a few different foods, such as cardamoms, figs, and shiitakes. Cardiolipin is found in Salix reticulata. Cardiolipin was first documented in 2000 (PMID: 10799718). This could make CL(18:0/18:0/18:0/18:0) A potential biomarker for the consumption of these foods (PMID: 18425414) (PMID: 19413994) (PMID: 16442164) (PMID: 16973164) (PMID: 16226238) (PMID: 12531542). |
|---|
| Structure | [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=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 |
|---|
| Synonyms | | Value | Source |
|---|
| 1,1'2,2'-Tetra-dodecanoyl cardiolipin | ChEBI | | 1,1'2,2'-Tetra-dodecanoylcardiolipin | ChEBI | | 1,1'2,2'-Tetrastearoyl cardiolipin | ChEBI | | 1,1'2,2'-Tetrastearoylcardiolipin | ChEBI | | Tetra-dodecanoyl cardiolipin | ChEBI | | Tetra-dodecanoylcardiolipin | ChEBI | | Tetrastearoylcardiolipin | ChEBI | | 1'-[1,2-Distearoyl-rac-glycero-3-phospho],3'-[1,2-distearoyl-rac-glycero-3-phospho]-glycerol | HMDB | | 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 | | Cardiolipins | HMDB | | Diphosphatidylglycerols | HMDB | | 1'-[1,2-Dioctadecanoyl-rac-glycero-3-phospho],3'-[1,2-dioctadecanoyl-rac-glycero-3-phospho]-glycerol | HMDB | | Cardiolipin | HMDB | | CL(18:0/18:0/18:0/18:0) | Lipid Annotator |
|
|---|
| Chemical Formula | C81H158O17P2 |
|---|
| Average Mass | 1466.0585 Da |
|---|
| Monoisotopic Mass | 1465.09743 Da |
|---|
| IUPAC Name | [(2R)-2,3-bis(octadecanoyloxy)propoxy][3-({[(2R)-2,3-bis(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid |
|---|
| Traditional Name | cardiolipin |
|---|
| CAS Registry Number | Not 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 Key | XVTUQDWPJJBEHJ-KZCWQMDCSA-N |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| Not Available | | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Glycerophospholipids |
|---|
| Sub Class | Glycerophosphoglycerophosphoglycerols |
|---|
| Direct Parent | Cardiolipins |
|---|
| 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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| 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 | |
|---|
| General References | - Houtkooper RH, Vaz FM: Cardiolipin, the heart of mitochondrial metabolism. Cell Mol Life Sci. 2008 Aug;65(16):2493-506. doi: 10.1007/s00018-008-8030-5. [PubMed:18425414 ]
- Schlame M, Ren M: The role of cardiolipin in the structural organization of mitochondrial membranes. Biochim Biophys Acta. 2009 Oct;1788(10):2080-3. doi: 10.1016/j.bbamem.2009.04.019. Epub 2009 May 4. [PubMed:19413994 ]
- 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 ]
- 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 ]
- 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 ]
- Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. doi: 10.1016/s0163-7827(00)00005-9. [PubMed:10799718 ]
- McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. doi: 10.1016/s1388-1981(02)00329-3. [PubMed:12531542 ]
- Dieude M, Striegl H, Tyznik AJ, Wang J, Behar SM, Piccirillo CA, Levine JS, Zajonc DM, Rauch J: Cardiolipin binds to CD1d and stimulates CD1d-restricted gammadelta T cells in the normal murine repertoire. J Immunol. 2011 Apr 15;186(8):4771-81. doi: 10.4049/jimmunol.1000921. Epub 2011 Mar 9. [PubMed:21389252 ]
- Abe M, Niibayashi R, Koubori S, Moriyama I, Miyoshi H: Molecular mechanisms for the induction of peroxidase activity of the cytochrome c-cardiolipin complex. Biochemistry. 2011 Oct 4;50(39):8383-91. doi: 10.1021/bi2010202. Epub 2011 Sep 12. [PubMed:21877718 ]
|
|---|