Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 06:32:17 UTC |
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Update Date | 2022-11-30 19:26:24 UTC |
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HMDB ID | HMDB0115955 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | CDP-DG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of clupanodonic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids). |
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Structure | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C50H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h5,7,11,13-14,16-18,20-21,24,26,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,15,19,22-23,25,27-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,13-11-,16-14-,18-17-,21-20-,26-24-/t42-,43-,47+,48?,49-/m1/s1 |
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Synonyms | Value | Source |
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1-palmitoleoyl-2-clupanodonoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-palmitoleoyl-2-clupanodonoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(16:1/22:5) | SMPDB, HMDB | CDP-DG(16:1n7/22:5n3) | SMPDB, HMDB | CDP-DG(16:1w7/22:5w3) | SMPDB, HMDB | CDP-DG(38:6) | SMPDB, HMDB | CDP-diacylglycerol(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | CDP-diacylglycerol(16:1/22:5) | SMPDB, HMDB | CDP-diacylglycerol(16:1n7/22:5n3) | SMPDB, HMDB | CDP-diacylglycerol(16:1w7/22:5w3) | SMPDB, HMDB | CDP-diacylglycerol(38:6) | SMPDB, HMDB | CDP-DG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C50H81N3O15P2 |
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Average Molecular Weight | 1026.152 |
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Monoisotopic Molecular Weight | 1025.514292916 |
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IUPAC Name | {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid |
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Traditional Name | [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C50H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h5,7,11,13-14,16-18,20-21,24,26,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,15,19,22-23,25,27-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,13-11-,16-14-,18-17-,21-20-,26-24-/t42-,43-,47+,48?,49-/m1/s1 |
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InChI Key | DIMKNDAYPKTGCZ-XIYAEOIESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | CDP-glycerols |
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Direct Parent | CDP-diacylglycerols |
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Alternative Parents | |
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Substituents | - Cdp-diacylglycerol
- Pyrimidine ribonucleoside diphosphate
- Diacyl-glycerol-3-pyrophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Aminopyrimidine
- Fatty acid ester
- Pyrimidone
- Monoalkyl phosphate
- Imidolactam
- Pyrimidine
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Dicarboxylic acid or derivatives
- Hydropyrimidine
- Organic phosphoric acid derivative
- Monosaccharide
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- Amino acid or derivatives
- 1,2-diol
- Carboxylic acid ester
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Alcohol
- Organonitrogen compound
- Organic nitrogen compound
- Organooxygen compound
- Amine
- Carbonyl group
- Primary amine
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0026972)
- Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027071)
- Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027352)
- Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027404)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027498)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027531)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027610)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027642)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027690)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027737)
- Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027773)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027808)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027852)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027853)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027854)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z)) (PathBank: SMP0027855)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0027856)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027857)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027858)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:1(9Z)) (PathBank: SMP0027859)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0027860)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0027861)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027862)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027863)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:1(9Z)) (PathBank: SMP0027864)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0027865)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027866)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027867)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0027868)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0027869)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027870)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027871)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0027872)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0027873)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0027874)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0027875)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0027876)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0027877)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0027878)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027879)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027880)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027881)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027882)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0027883)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0027884)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0027885)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0027886)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0027887)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0027888)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027889)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027890)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027891)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0027892)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0027893)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027894)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027895)
- Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0027975)
- Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028018)
- Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028286)
- Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028335)
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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