Showing chemical card for CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)) (CFc000091294)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:01:41 UTC

Chemfont ID

CFc000091294

Molecule Identification

Common Name

CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z))

Definition

CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)) contains three chains of (8Z-hexadecenoyl) at the C1, C2 and C4 positions, one chain of (9Z,12Z-octadecadienoyl) at the C3 position. 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

SMILES for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

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

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INCHI for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

InChI=1S/C75H136O17P2/c1-2-3-4-5-6-7-8-9-10-17-24-31-38-45-52-59-75(80)88-69-74(87-65-58-51-44-37-30-23-16-13-20-27-34-41-48-55-62-78)71-92-94(83,84)90-67-72(79)66-89-93(81,82)91-70-73(86-64-57-50-43-36-29-22-15-12-19-26-33-40-47-54-61-77)68-85-63-56-49-42-35-28-21-14-11-18-25-32-39-46-53-60-76/h6-7,9-16,60-62,72-74,79H,2-5,8,17-59,63-71H2,1H3,(H,81,82)(H,83,84)/b7-6-,10-9-,14-11-,15-12-,16-13-/t72-,73+,74+/m0/s1

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Structure for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

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3D Structure for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

Synonyms

Value	Source
[(2S)-3-({[(2R)-2,3-bis({[(8Z)-16-oxohexadec-8-en-1-yl]oxy})propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-{[(8Z)-16-oxohexadec-8-en-1-yl]oxy}propoxy]phosphinate	Generator

Chemical Formula

C₇₅H₁₃₆O₁₇P₂

Average Molecular Weight

1371.844

Monoisotopic Molecular Weight

1370.925276915

IUPAC Name

[(2S)-3-({[(2R)-2,3-bis({[(8Z)-16-oxohexadec-8-en-1-yl]oxy})propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-{[(8Z)-16-oxohexadec-8-en-1-yl]oxy}propoxy]phosphinic acid

Traditional Name

(2S)-3-{[(2R)-2,3-bis({[(8Z)-16-oxohexadec-8-en-1-yl]oxy})propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-{[(8Z)-16-oxohexadec-8-en-1-yl]oxy}propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C75H136O17P2/c1-2-3-4-5-6-7-8-9-10-17-24-31-38-45-52-59-75(80)88-69-74(87-65-58-51-44-37-30-23-16-13-20-27-34-41-48-55-62-78)71-92-94(83,84)90-67-72(79)66-89-93(81,82)91-70-73(86-64-57-50-43-36-29-22-15-12-19-26-33-40-47-54-61-77)68-85-63-56-49-42-35-28-21-14-11-18-25-32-39-46-53-60-76/h6-7,9-16,60-62,72-74,79H,2-5,8,17-59,63-71H2,1H3,(H,81,82)(H,83,84)/b7-6-,10-9-,14-11-,15-12-,16-13-/t72-,73+,74+/m0/s1

InChI Key

ZGWROKHTWCBXTA-LTQVQTFTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophosphoglycerophosphoglycerols. These are glycerophospholipids that contain three glycerol moieties sequentially linked to each other with a phosphate group. They include cardiolipins.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphoglycerols

Direct Parent

Glycerophosphoglycerophosphoglycerols

Alternative Parents

Glycerol ethers
Fatty acid esters
Dialkyl phosphates
Alpha-hydrogen aldehydes
Secondary alcohols
Carboxylic acid esters
Monocarboxylic acids and derivatives
Dialkyl ethers
Organic oxides
Hydrocarbon derivatives

Substituents

Glycerophosphoglycerophosphoglycerol
Fatty acid ester
Glycerol ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Alpha-hydrogen aldehyde
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Aldehyde
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Non-alcoholic fatty liver disease (PMID: 17900521)

Genetic disorder

Nontypified gene mutation

Mitochondrial diseases

Tangier disease (PMID: 11111099)

Inborn errors of metabolism

3-Methylglutaconic aciduria type II, X-linked (PMID: 17082194)

Circulatory system disorder

Cardiac disorder

Diabetic heart disease (PMID: 17487985)

Nonspecific condition

Aging (PMID: 1629722)

Disposition

Biological location

Cellular substructure

Inner mitochondrial membrane (PMID: 31315173)

Source

Endogenous

Endogenous (HMDB: HMDB0110885)

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	7.7e-05 g/L	ALOGPS
logP	8.98	ALOGPS
logP	19.5	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	236.95 Å²	ChemAxon
Rotatable Bond Count	78	ChemAxon
Refractivity	387.84 m³·mol⁻¹	ChemAxon
Polarizability	164.93 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

HMDB0110885

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(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)) (CFc000091294)

MOL for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

3D MOL for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

3D SDF for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

3D-SDF for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

PDB for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

3D PDB for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

SMILES for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

INCHI for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

Structure for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))

3D Structure for CFc000091294 (CL(16:1(8Z)/16:1(8Z)/18:2(9Z,12Z)/16:1(8Z)))