Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 12:18:04 UTC
Update Date2022-09-01 00:05:40 UTC
Metabolite IDMMDBc0043526
Metabolite Identification
Common Name1-MLCL(0:0/14:0/15:0/22:0)
Description1-MLCL(0:0/14:0/15:0/22:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 1-MLCL(0:0/14:0/15:0/22:0) contains one chain of at the C1 position, one chain of tetradecanoic acid at the C2 position, one chain of pentadecanoic acid at the C3 position, one chain of docosanoic acid at the C4 position. MLCL is present in eukaryotes as part of the metabolic cycle of mitochondrial lipids. Removal of one acyl chain from a cardiolipin results in generation of monolysocardiolipin (MLCL). MLCL has been used as an inter­mediate in the synthesis of spin-labeled CL to study the interaction of CL with mitochondrial enzymes. Because a role for MLCL has been suggested in apoptosis, this molecule has been used to study its interaction with various enzymes involved in lipid remodeling and apoptosis. There are two species of monolysocardiolipins, 1-MLCL which is missing a fatty acid in position R1 the and 2-MLCL which is missing a fatty acid in position R4.
Structure
Synonyms
ValueSource
[(2R)-2-(Docosanoyloxy)-3-(pentadecanoyloxy)propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-hydroxy-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinateGenerator
Molecular FormulaC60H118O16P2
Average Mass1157.536
Monoisotopic Mass1156.789511716
IUPAC Name[(2R)-2-(docosanoyloxy)-3-(pentadecanoyloxy)propoxy][(2S)-2-hydroxy-3-({hydroxy[(2R)-3-hydroxy-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid
Traditional Name(2R)-2-(docosanoyloxy)-3-(pentadecanoyloxy)propoxy((2S)-2-hydroxy-3-{[hydroxy((2R)-3-hydroxy-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(CO)OC(=O)CCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C60H118O16P2/c1-4-7-10-13-16-19-22-24-25-26-27-28-29-30-33-36-39-42-45-48-60(65)76-57(52-70-58(63)46-43-40-37-34-32-23-20-17-14-11-8-5-2)54-74-78(68,69)72-51-55(62)50-71-77(66,67)73-53-56(49-61)75-59(64)47-44-41-38-35-31-21-18-15-12-9-6-3/h55-57,61-62H,4-54H2,1-3H3,(H,66,67)(H,68,69)/t55-,56+,57+/m0/s1
InChI KeyHBCIFYCLBBWRFS-XSJPGQJYSA-N