ChemFOnt: Showing chemical card for CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (CFc000037299)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:37:05 UTC

Chemfont ID

CFc000037299

Molecule Identification

Common Name

CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))

Definition

CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a cardiolipin (CL). Cardiolipins are sometimes called 'double' phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol 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. CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) contains one chain of hexadecanoic acid at the C1 position, one chain of (5Z,8Z,11Z,14Z-eicosatetraenoyl) at the C2 position, one chain of (7Z,10Z,13Z,16Z,19Z-docosapentaenoyl) at the C3 position, one chain of (4Z,7Z,10Z,13Z,16Z-docosapentaenoyl) at the C4 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 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 ). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1'-[1-Palmitoyl-2-arachidonoyl-sn-glycero-3-phospho],3'-[1,2-didocosapentaenoyl-rac-glycero-3-phospho]-glycerol	HMDB
Cardiolipin(16:0/20:4/22:5/22:5)	HMDB
Cardiolipin(80:14)	HMDB
CL(1'-[16:0/20:4(5Z,8Z,11Z,14Z)],3'-[22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)])	HMDB
CL(16:0/20:4/22:5/22:5)	HMDB
CL(80:14)	HMDB
1'-[1-Hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho],3'-[1,2-di(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-rac-glycero-3-phospho]-glycerol	HMDB
CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))	Lipid Annotator

Chemical Formula

C₈₉H₁₄₆O₁₇P₂

Average Molecular Weight

1550.078

Monoisotopic Molecular Weight

1549.003527237

IUPAC Name

[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy][(2S)-3-({[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

Traditional Name

(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy((2S)-3-{[(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

CAS Registry Number

None

SMILES

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C89H146O17P2/c1-5-9-13-17-21-25-29-33-36-39-41-44-46-50-54-58-62-66-70-74-87(92)100-80-85(106-89(94)76-72-68-64-60-56-52-48-45-42-40-37-34-30-26-22-18-14-10-6-2)82-104-108(97,98)102-78-83(90)77-101-107(95,96)103-81-84(79-99-86(91)73-69-65-61-57-53-49-32-28-24-20-16-12-8-4)105-88(93)75-71-67-63-59-55-51-47-43-38-35-31-27-23-19-15-11-7-3/h9,13,21-23,25-27,33-38,41-42,44-45,47,50-52,54,56,59,63-64,68,83-85,90H,5-8,10-12,14-20,24,28-32,39-40,43,46,48-49,53,55,57-58,60-62,65-67,69-82H2,1-4H3,(H,95,96)(H,97,98)/b13-9-,25-21-,26-22-,27-23-,36-33-,37-34-,38-35-,44-41-,45-42-,51-47-,54-50-,56-52-,63-59-,68-64-/t83-,84+,85+/m0/s1

InChI Key

LUTXCNQTCKPOLP-RZSNZREKSA-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)
Membrane (HMDB: HMDB0056773)
Cytoplasm (HMDB: HMDB0056773)
Cell membrane (HMDB: HMDB0056773)
Intracellular membrane (HMDB: HMDB0056773)

Organelle

Mitochondrion (HMDB: HMDB0056773)
Endoplasmic reticulum (HMDB: HMDB0056773)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0056773)

Organ

Heart (HMDB: HMDB0056773)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0056773)

Source

Endogenous

Endogenous (HMDB: HMDB0056773)

Animal

Animal (HMDB: HMDB0056773)

Exogenous

Food

Food (HMDB: HMDB0056773)

Process

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.5e-05 g/L	ALOGPS
logP	9.05	ALOGPS
logP	25.76	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	459.35 m³·mol⁻¹	ChemAxon
Polarizability	181.15 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

HMDB0056773

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031798

KNApSAcK ID

Not Available

Chemspider ID

74855098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131767147

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (CFc000037299)

MOL for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

3D MOL for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

3D SDF for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

3D-SDF for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

PDB for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

3D PDB for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

SMILES for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

INCHI for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

Structure for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))

3D Structure for CFc000037299 (CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)))