2-MLCL(12:0/12:0/30:0/0:0) (YMDB12000)

Identification

YMDB ID

YMDB12000

Name

2-MLCL(12:0/12:0/30:0/0:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

2-MLCL(12:0/12:0/30:0/0:0) is a monolysocardiolipin (MLCL). Monolysocardiolipins have three fatty acid tails, instead of the usual two. 2-MLCL(12:0/12:0/30:0/0:0) contains two chains of dodecanoic acid at the C1 and C2 positions, one chain of tricontanoic acid at the C3 position, one chain of 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 1199.617
Monoisotopic: 1198.836461909

InChI Key

ZPZFSMOLLNHTRB-UPMPAGDASA-N

InChI

InChI=1S/C63H124O16P2/c1-4-7-10-13-16-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33-34-35-36-39-41-43-46-49-61(66)73-52-58(64)53-75-80(69,70)76-54-59(65)55-77-81(71,72)78-57-60(79-63(68)51-48-45-42-38-18-15-12-9-6-3)56-74-62(67)50-47-44-40-37-17-14-11-8-5-2/h58-60,64-65H,4-57H2,1-3H3,(H,69,70)(H,71,72)/t58-,59-,60-/m1/s1

IUPAC Name

[(2R)-2,3-bis(dodecanoyloxy)propoxy][(2R)-2-hydroxy-3-({hydroxy[(2R)-2-hydroxy-3-(triacontanoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

Traditional IUPAC Name

(2R)-2,3-bis(dodecanoyloxy)propoxy((2R)-2-hydroxy-3-{[hydroxy((2R)-2-hydroxy-3-(triacontanoyloxy)propoxy)phosphoryl]oxy}propoxy)phosphinic acid

Chemical Formula

C₆₃H₁₂₄O₁₆P₂

SMILES

[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC

Chemical Taxonomy

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0001 g/L	ALOGPS
logP	8.72	ALOGPS
logP	19.46	ChemAxon
logS	-7.1	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	4	ChemAxon
Polar Surface Area	230.88 Å²	ChemAxon
Rotatable Bond Count	68	ChemAxon
Refractivity	324.12 m³·mol⁻¹	ChemAxon
Polarizability	144.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Mitochondrion membrane

Organoleptic Properties

Not Available

SMPDB Pathways

Cardiolipin Biosynthesis CL(10:0/12:0/12:0/30:0)	PW003748
Cardiolipin Biosynthesis CL(12:0/12:0/12:0/30:0)	PW005885

KEGG Pathways

Not Available

SMPDB Reactions

2-MLCL(12:0/12:0/30:0/0:0) → CL(10:0/12:0/12:0/30:0)

2-MLCL(12:0/12:0/30:0/0:0) → CL(12:0/12:0/12:0/30:0)

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-2910452204-b34ba331b7410af63471	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0540-2710595202-7edf83b37087c776b9fc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7550796100-e9169bad8f5af9588fe1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f7k-1900711101-284ad8e011445eb032b8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fc1-7900811100-409a535f0350260e917b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9220220000-0f9d5af9bed446ff49c9	JSpectraViewer

References

References:

Baile MG, Lu YW, Claypool SM. (2014). "The topology and regulation of cardiolipin biosynthesis and remodeling in yeast." Chem Phys Lipids. 2014 Apr;179:25-31. doi: 10.1016/j.chemphyslip.2013.10.008. Epub 2013 Nov 1.24184646

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0x8f86907c>