Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-11 04:51:40 UTC
Update Date2022-11-30 19:27:19 UTC
HMDB IDHMDB0118068
Secondary Accession NumbersNone
Metabolite Identification
Common NameCL(8:0/11:0/12:0/a-17:0)
DescriptionCL(8:0/11:0/12:0/a-17:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(8:0/11:0/12:0/a-17:0) contains one chain of octanoic acid at the C1 position, one chain of undecanoic acid at the C2 position, one chain of dodecanoic acid at the C3 position, one chain of 14-methylhexadecanoic acid at the C4 position. 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 will 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 ). Tafazzin is an important enzyme in the remodeling of cardiolipins, and opposite to cardiolipin synthase, it shows strong acyl specificity. This suggest that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipin and is the cause of Barth syndrome (BTHS), a X-linked human disease (PMID: 16973164 ). BTHS patients seems to lack acyl specificity and as a result, there are many potential cardiolipin species that can exists (PMID: 16226238 ). Common fatty acyl chains determined through methods such as gas chromatography and high-performance liquid chromatography are used to generate various cardiolipins and a representative molecule is chosen from each variation.
Structure
Data?1563873927
Synonyms
ValueSource
1'-[1-capryloyl-2-animal fats-sn-glycero-3-phospho],3'-[1,2-didodecanoyl-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
CL(8:0/11:0/12:0/12:0)Lipid Annotator, HMDB
CL(43:0)Lipid Annotator, HMDB
CL(1'-[8:0/11:0],3'-[12:0/12:0])Lipid Annotator, HMDB
Cardiolipin(43:0)Lipid Annotator, HMDB
1'-[1-octanoyl-2-undecanoic acid-sn-glycero-3-phospho],3'-[1,2-didodecanoyl-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
Cardiolipin(8:0/11:0/12:0/12:0)Lipid Annotator, HMDB
CL(8:0/11:0/12:0/a-17:0)Lipid Annotator
[(2R)-3-(Dodecanoyloxy)-2-[(14-methylhexadecanoyl)oxy]propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-(octanoyloxy)-2-(undecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinateGenerator, HMDB
Chemical FormulaC57H110O17P2
Average Molecular Weight1129.438
Monoisotopic Molecular Weight1128.721826078
IUPAC Name[(2R)-3-(dodecanoyloxy)-2-[(14-methylhexadecanoyl)oxy]propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-(octanoyloxy)-2-(undecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional Name(2R)-3-(dodecanoyloxy)-2-[(14-methylhexadecanoyl)oxy]propoxy((2S)-2-hydroxy-3-{[hydroxy((2R)-3-(octanoyloxy)-2-(undecanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC)OC(=O)CCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC(C)CC
InChI Identifier
InChI=1S/C57H110O17P2/c1-6-10-13-16-18-22-27-31-36-41-55(60)68-47-53(74-57(62)43-38-33-28-24-21-20-23-25-30-34-39-50(5)9-4)49-72-76(65,66)70-45-51(58)44-69-75(63,64)71-48-52(46-67-54(59)40-35-29-15-12-8-3)73-56(61)42-37-32-26-19-17-14-11-7-2/h50-53,58H,6-49H2,1-5H3,(H,63,64)(H,65,66)/t50?,51-,52+,53+/m0/s1
InChI KeyOXRXJRDQSOJZJY-YDFVMMAWSA-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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.7ALOGPS
logP16.44ChemAxon
logS-6.4ALOGPS
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 Count61ChemAxon
Refractivity296.43 m³·mol⁻¹ChemAxon
Polarizability129.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+354.89530932474
DeepCCS[M-H]-352.09830932474
DeepCCS[M-2H]-386.70730932474
DeepCCS[M+Na]+362.07730932474
AllCCS[M+H]+343.332859911
AllCCS[M+H-H2O]+343.632859911
AllCCS[M+NH4]+343.132859911
AllCCS[M+Na]+343.032859911
AllCCS[M-H]-349.532859911
AllCCS[M+Na-2H]-355.232859911
AllCCS[M+HCOO]-361.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - CL(8:0/11:0/12:0/a-17:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/11:0/12:0/a-17:0) 10V, Negative-QTOFsplash10-03di-0410090000-bf2c1e306e4f147f0da32017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/11:0/12:0/a-17:0) 20V, Negative-QTOFsplash10-03di-0433390000-f097a3cfe8a0ab27c33a2017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/11:0/12:0/a-17:0) 40V, Negative-QTOFsplash10-00rm-0954200000-c043545eb95046448a442017-10-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131824677
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. 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 ]
  8. Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. [PubMed:10799718 ]
  9. McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. [PubMed:12531542 ]
  10. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.