ChemFOnt: Showing chemical card for CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000092425)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:03:20 UTC

Chemfont ID

CFc000092425

Molecule Identification

Common Name

CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))

Definition

CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) contains two chains of (5Z,8Z,11Z,14Z-eicosatetraenoyl) at the C1 and C4 positions, two chains of (9Z,12Z-octadecadienoyl) at the C2 and C3 positions. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CL(1'-[20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])	Lipid Annotator, HMDB
Cardiolipin(74:10)	Lipid Annotator, HMDB
Cardiolipin(20:4/18:2/18:2/18:2)	Lipid Annotator, HMDB
CL(74:10)	Lipid Annotator, HMDB
CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))	Lipid Annotator
1'-[1-arachidonoyl-2-linoleoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol	Lipid Annotator, HMDB
1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol	Lipid Annotator, HMDB
CL(20:4/18:2/18:2/18:2)	Lipid Annotator, HMDB

Chemical Formula

C₈₅H₁₄₂O₁₇P₂

Average Molecular Weight

1498.002

Monoisotopic Molecular Weight

1496.972227108

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid

Traditional Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphoryl]oxy}propoxy((2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C85H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)77-99-103(91,92)97-73-79(86)74-98-104(93,94)100-78-81(75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3)102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2/h21-28,33-38,41-44,46,48,54,56,58,60,79-81,86H,5-20,29-32,39-40,45,47,49-53,55,57,59,61-78H2,1-4H3,(H,91,92)(H,93,94)/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,41-35-,42-36-,46-43-,48-44-,58-54-,60-56-/t79-,80+,81+/m0/s1

InChI Key

LFAQBTPICLRWOR-HWTDHADRSA-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)
Cell membrane (HMDB: HMDB0112016)
Intracellular membrane (HMDB: HMDB0112016)

Organelle

Endoplasmic reticulum (HMDB: HMDB0112016)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0112016)

Organ

Heart (HMDB: HMDB0112016)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0112016)

Source

Endogenous

Endogenous (HMDB: HMDB0112016)

Animal

Animal (HMDB: HMDB0112016)

Exogenous

Food

Food (HMDB: HMDB0112016)

Process

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.5e-05 g/L	ALOGPS
logP	9.09	ALOGPS
logP	24.7	ChemAxon
logS	-7.2	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	78	ChemAxon
Refractivity	438.71 m³·mol⁻¹	ChemAxon
Polarizability	174.53 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

HMDB0112016

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB083610

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

118702657

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000092425)

MOL for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

3D MOL for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

3D SDF for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

3D-SDF for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

PDB for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

3D PDB for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

SMILES for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

INCHI for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

Structure for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))

3D Structure for CFc000092425 (CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)))