CHEBI:28494 - cardiolipin

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ChEBI Name cardiolipin
Definition A phosphatidylglycerol composed of two molecules of phosphatidic acid covalently linked to a molecule of glycerol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41403, CHEBI:3411, CHEBI:23037
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Formula C13H18O17P2R4
Net Charge 0
Average Mass (excl. R groups) 508.21930
Monoisotopic Mass (excl. R groups) 508.00192
SMILES OC(COP(O)(=O)OC[C@@H](COC([*])=O)OC([*])=O)COP(O)(=O)OC[C@@H](COC([*])=O)OC([*])=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
(via phosphatidylglycerol )
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via phosphatidylglycerol )
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ChEBI Ontology
Outgoing cardiolipin (CHEBI:28494) has role Escherichia coli metabolite (CHEBI:76971)
cardiolipin (CHEBI:28494) has role human metabolite (CHEBI:77746)
cardiolipin (CHEBI:28494) has role mouse metabolite (CHEBI:75771)
cardiolipin (CHEBI:28494) is a glycerophosphoglycerophosphoglycerol (CHEBI:166988)
cardiolipin (CHEBI:28494) is a phosphatidylglycerol (CHEBI:17517)
cardiolipin (CHEBI:28494) is conjugate acid of cardiolipin(2−) (CHEBI:62237)
Incoming acetyl cardiolipin (CHEBI:60353) has functional parent cardiolipin (CHEBI:28494)
dimethyl cardiolipin (CHEBI:60352) has functional parent cardiolipin (CHEBI:28494)
1',3'-bis-[1-hexadecanoyl-2-(11Z-octadecenoyl)-sn-glycero-3-phospho]-sn-glycerol (CHEBI:137162) is a cardiolipin (CHEBI:28494)
1,1ʼ,2-trilinoleoyl-2ʼ-oleoyl cardiolipin (CHEBI:84399) is a cardiolipin (CHEBI:28494)
1,1ʼ,2-trilinoleoyl-2ʼ-palmitoyl cardiolipin (CHEBI:84400) is a cardiolipin (CHEBI:28494)
1-O,3-O-Bis(1-O,2-O-dioctanoyl-L-glycero-3-phospho)-L-glycerol (CHEBI:185267) is a cardiolipin (CHEBI:28494)
12-aminolauroyl tripalmitoyl cardiolipin (CHEBI:74829) is a cardiolipin (CHEBI:28494)
cardiolipin (18:2/18:2/18:2/18:3) (CHEBI:134553) is a cardiolipin (CHEBI:28494)
cardiolipin (18:3/18:1/18:3/20:3) (CHEBI:134554) is a cardiolipin (CHEBI:28494)
cardiolipin (20:2/16:1/18:1/18:3) (CHEBI:134555) is a cardiolipin (CHEBI:28494)
cardiolipin 66:1 (CHEBI:167193) is a cardiolipin (CHEBI:28494)
cardiolipin 66:4 (CHEBI:166989) is a cardiolipin (CHEBI:28494)
cardiolipin 68:4 (CHEBI:166990) is a cardiolipin (CHEBI:28494)
cardiolipin 70:1 (CHEBI:167194) is a cardiolipin (CHEBI:28494)
cardiolipin 72:6 (CHEBI:166991) is a cardiolipin (CHEBI:28494)
CL(1'-[16:0/18:2(9Z,12Z)],3'-[16:0/16:0]) (CHEBI:186586) is a cardiolipin (CHEBI:28494)
CL(1'-[16:0/18:2(9Z,12Z)],3'-[16:0/18:1(9Z)]) (CHEBI:186580) is a cardiolipin (CHEBI:28494)
CL(1'-[16:0/18:2(9Z,12Z)],3'-[16:0/18:2(9Z,12Z)]) (CHEBI:186583) is a cardiolipin (CHEBI:28494)
CL(1'-[16:0/18:2(9Z,12Z)],3'-[20:0/16:0]) (CHEBI:186590) is a cardiolipin (CHEBI:28494)
CL(1'-[18:0/18:1(9Z)],3'-[16:0/18:1(9Z)]) (CHEBI:186592) is a cardiolipin (CHEBI:28494)
CL(1'-[18:0/18:2(9Z,12Z)],3'-[20:0/16:0]) (CHEBI:186595) is a cardiolipin (CHEBI:28494)
CL(1'-[18:1(9Z)/16:0],3'-[18:0/18:1(9Z)]) (CHEBI:186591) is a cardiolipin (CHEBI:28494)
CL(1'-[18:1(9Z)/18:1(9Z)],3'-[16:0/18:2(9Z,12Z)]) (CHEBI:186588) is a cardiolipin (CHEBI:28494)
CL(1'-[18:1(9Z)/18:1(9Z)],3'-[18:1(9Z)/18:0]) (CHEBI:186594) is a cardiolipin (CHEBI:28494)
CL(1'-[18:1(9Z)/20:4(5Z,8Z,11Z,14Z)],3'-[18:2(9Z,12Z)/18:0]) (CHEBI:186587) is a cardiolipin (CHEBI:28494)
CL(1'-[18:2(9Z,12Z)/16:0],3'-[18:2(9Z,12Z)/18:1(9Z)]) (CHEBI:186576) is a cardiolipin (CHEBI:28494)
CL(1'-[18:2(9Z,12Z)/18:0],3'-[18:1(9Z)/16:0]) (CHEBI:186585) is a cardiolipin (CHEBI:28494)
CL(1'-[18:2(9Z,12Z)/18:2(9Z,12Z)],3'-[18:1(9Z)/16:0]) (CHEBI:186584) is a cardiolipin (CHEBI:28494)
CL(1'-[20:4(5Z,8Z,11Z,14Z)/16:0],3'-[16:0/18:1(9Z)]) (CHEBI:186578) is a cardiolipin (CHEBI:28494)
CL(1'-[20:4(5Z,8Z,11Z,14Z)/18:0],3'-[18:1(9Z)/18:1(9Z)]) (CHEBI:186593) is a cardiolipin (CHEBI:28494)
CL(1'-[20:4(5Z,8Z,11Z,14Z)/20:0],3'-[18:0/16:0]) (CHEBI:186596) is a cardiolipin (CHEBI:28494)
CL(16:0/18:1(11Z)/18:0/18:0) (CHEBI:180833) is a cardiolipin (CHEBI:28494)
CL(70:9) (CHEBI:189612) is a cardiolipin (CHEBI:28494)
CL(8:0/10:0/10:0/11:0) (CHEBI:192194) is a cardiolipin (CHEBI:28494)
CL(i-13:0/i-24:0/i-13:0/18:2(9Z,11Z)) (CHEBI:192195) is a cardiolipin (CHEBI:28494)
reduced cardiolipin (CHEBI:60457) is a cardiolipin (CHEBI:28494)
tetrahexadec-9-enoyl cardiolipin (CHEBI:104873) is a cardiolipin (CHEBI:28494)
tetrahexadecanoyl cardiolipin (CHEBI:104586) is a cardiolipin (CHEBI:28494)
tetralinoleoyl cardiolipin (CHEBI:84398) is a cardiolipin (CHEBI:28494)
tetramyristoyl cardiolipin (CHEBI:62862) is a cardiolipin (CHEBI:28494)
tetraoctadec-11-enoyl cardiolipin (CHEBI:105685) is a cardiolipin (CHEBI:28494)
tetraoleyl cardiolipin (CHEBI:60356) is a cardiolipin (CHEBI:28494)
tetrastearoyl cardiolipin (CHEBI:62861) is a cardiolipin (CHEBI:28494)
cardiolipin(2−) (CHEBI:62237) is conjugate base of cardiolipin (CHEBI:28494)
Synonyms Sources
1',3'-Bis(1,2-diacyl-sn-glycero-3-phospho)-sn-glycerol KEGG COMPOUND
cardiolipins ChEBI
Diphosphatidylglycerol KEGG COMPOUND
Manual Xrefs Databases
Cardiolipin Wikipedia
DB03429 DrugBank
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Citations Waiting for Citations Types Sources
10540156 PubMed citation Europe PMC
11339809 PubMed citation Europe PMC
16341241 PubMed citation Europe PMC
1694860 PubMed citation Europe PMC
17294083 PubMed citation Europe PMC
18515061 PubMed citation Europe PMC
18790112 PubMed citation Europe PMC
19303420 PubMed citation Europe PMC
19962311 PubMed citation Europe PMC
22819940 PubMed citation Europe PMC
2413066 PubMed citation Europe PMC
28458255 PubMed citation Europe PMC
3196084 PubMed citation Europe PMC
Last Modified
02 December 2020
General Comment
2011-01-18 Cardiolipins have four acyl chains which are usually unsaturated, though the specific fatty acids vary depending on the organisms.