ChemFOnt: Showing chemical card for CL(8:0/a-15:0/i-16:0/i-22:0) (CFc000102457)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:18:01 UTC

Chemfont ID

CFc000102457

Molecule Identification

Common Name

CL(8:0/a-15:0/i-16:0/i-22:0)

Definition

CL(8:0/a-15:0/i-16:0/i-22:0) 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/a-15:0/i-16:0/i-22:0) contains one chain of octanoic acid at the C1 position, one chain of 12-methyltetradecanoic acid at the C2 position, one chain of 14-methylpentadecanoic acid at the C3 position, one chain of 20-methylheneicosanoic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(12-methyltetradecanoyl)oxy]-3-(octanoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(20-methylhenicosanoyl)oxy]-3-[(14-methylpentadecanoyl)oxy]propoxy]phosphinate	HMDB
1'-[1-Capryloyl-2-anteisopentadecanoyl-sn-glycero-3-phospho],3'-[1,2-diisohexadecanoyl-rac-glycero-3-phospho]-glycerol	HMDB
1'-[1-Octanoyl-2-anteisopentadecanoyl-sn-glycero-3-phospho],3'-[1,2-diisohexadecanoyl-rac-glycero-3-phospho]-glycerol	HMDB
CL(8:0/A-15:0/I-16:0/I-16:0)	HMDB
Cardiolipin(55:0)	HMDB
Cardiolipin(8:0/A-15:0/I-16:0/I-16:0)	HMDB
CL(1'-[8:0/A-15:0],3'-[I-16:0/I-16:0])	HMDB
CL(55:0)	HMDB
CL(8:0/a-15:0/i-16:0/i-22:0)	Lipid Annotator

Chemical Formula

C₇₀H₁₃₆O₁₇P₂

Average Molecular Weight

1311.789

Monoisotopic Molecular Weight

1310.925276915

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(12-methyltetradecanoyl)oxy]-3-(octanoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(20-methylhenicosanoyl)oxy]-3-[(14-methylpentadecanoyl)oxy]propoxy]phosphinic acid

Traditional Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(12-methyltetradecanoyl)oxy]-3-(octanoyloxy)propoxy)phosphoryl]oxy}propoxy((2R)-2-[(20-methylhenicosanoyl)oxy]-3-[(14-methylpentadecanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC)OC(=O)CCCCCCCCCCC(C)CC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C70H136O17P2/c1-8-10-11-34-44-51-67(72)80-57-65(86-70(75)54-47-40-33-27-26-30-37-43-50-63(7)9-2)59-84-88(76,77)82-55-64(71)56-83-89(78,79)85-60-66(58-81-68(73)52-45-38-31-24-21-20-23-29-36-42-49-62(5)6)87-69(74)53-46-39-32-25-19-17-15-13-12-14-16-18-22-28-35-41-48-61(3)4/h61-66,71H,8-60H2,1-7H3,(H,76,77)(H,78,79)/t63?,64-,65+,66+/m0/s1

InChI Key

LBYPEKNLIDZYOM-ZTOXKGDWSA-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.

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

Not Available

Functional Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Inner mitochondrial membrane (PMID: 31315173)

Source

Endogenous

Endogenous (HMDB: HMDB0122048)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 19368971)

Biochemical process

Proton trap for oxidative phosphorylation (PMID: 12297275)

Role

Biological role

Stabilizing agent

Stabilizing cytochrome oxidase (PMID: 10413476)
Proton trap for oxidative phosphorylation (PMID: 12297275)
Stabilizing mitochondrial structure (PMID: 10413476;)

Molecular messenger

Apoptosis (PMID: 19368971)

Transporter

Cholesterol translocation (PMID: 11111099)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.5e-05 g/L	ALOGPS
logP	8.37	ALOGPS
logP	21.91	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	72	ChemAxon
Refractivity	356.14 m³·mol⁻¹	ChemAxon
Polarizability	157.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0122048

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74883696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131828645

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CL(8:0/a-15:0/i-16:0/i-22:0) (CFc000102457)

MOL for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

3D MOL for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

3D SDF for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

3D-SDF for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

PDB for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

3D PDB for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

SMILES for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

INCHI for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

Structure for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))

3D Structure for CFc000102457 (CL(8:0/a-15:0/i-16:0/i-22:0))