ChemFOnt: Showing chemical card for CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)) (CFc000302292)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 04:14:28 UTC

Chemfont ID

CFc000302292

Molecule Identification

Common Name

CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z))

Definition

CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)) contains one chain of (9Z-octadecenoyl) at the C1 position, two chains of (11Z,14Z,17Z-eicosatrienoyl) at the C2 and C4 positions, one chain of (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl) at the C3 position fatty acids. 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), an 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

Not Available

Chemical Formula

C₈₇H₁₄₆O₁₇P₂

Average Molecular Weight

1526.056

Monoisotopic Molecular Weight

1525.003527237

IUPAC Name

[(2R)-2-hydroxy-3-({hydroxy[(2R)-2-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphinic acid

Traditional Name

(2R)-2-hydroxy-3-{[hydroxy((2R)-2-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propoxy((2R)-2-[(11Z,14Z,17Z)-icosa-11,14,17-trienoyloxy]-3-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OC[C@@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCC\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C87H146O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h9-11,13-15,21-23,25-27,33-39,43-44,48,56,60,81-83,88H,5-8,12,16-20,24,28-32,40-42,45-47,49-55,57-59,61-80H2,1-4H3,(H,93,94)(H,95,96)/b13-9-,14-10-,15-11-,25-21-,26-22-,27-23-,37-33-,38-34-,39-35-,43-36-,48-44-,60-56-/t81-,82-,83-/m1/s1

InChI Key

HKFVGWCXYWPVLE-HQSQEANASA-N

Chemical Taxonomy

Classification

Not classified

Functional Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Inner mitochondrial membrane (PMID: 31315173)

Source

Endogenous

Endogenous (HMDB: HMDB0322777)

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	8.2e-05 g/L	ALOGPS
logP	9.14	ALOGPS
logP	25.59	ChemAxon
logS	-7.3	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	80	ChemAxon
Refractivity	447.91 m³·mol⁻¹	ChemAxon
Polarizability	178.85 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

HMDB0316159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)) (CFc000302292)

MOL for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

3D MOL for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

3D SDF for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

3D-SDF for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

PDB for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

3D PDB for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

SMILES for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

INCHI for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

Structure for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))

3D Structure for CFc000302292 (CL(18:1(9Z)/20:3(11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(11Z,14Z,17Z)))