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 06:34:40 UTC |
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Update Date | 2022-11-30 19:26:25 UTC |
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HMDB ID | HMDB0115968 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(18:2(9Z,12Z)/18:1(9Z)) |
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Description | CDP-DG(18:2(9Z,12Z)/18:1(9Z)) 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(18:2(9Z,12Z)/18:1(9Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of oleic 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/C\C=C/CCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C48H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h11,13,17-20,35-36,40-41,45-47,54-55H,3-10,12,14-16,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b13-11-,19-17-,20-18-/t40-,41-,45+,46?,47-/m1/s1 |
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Synonyms | Value | Source |
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1-linoleoyl-2-oleoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-linoleoyl-2-oleoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(18:2/18:1) | SMPDB, HMDB | CDP-DG(18:2n6/18:1n9) | SMPDB, HMDB | CDP-DG(18:2w6/18:1w9) | SMPDB, HMDB | CDP-DG(36:3) | SMPDB, HMDB | CDP-diacylglycerol(18:2(9Z,12Z)/18:1(9Z)) | SMPDB, HMDB | CDP-diacylglycerol(18:2/18:1) | SMPDB, HMDB | CDP-diacylglycerol(18:2n6/18:1n9) | SMPDB, HMDB | CDP-diacylglycerol(18:2w6/18:1w9) | SMPDB, HMDB | CDP-diacylglycerol(36:3) | SMPDB, HMDB | CDP-DG(18:2(9Z,12Z)/18:1(9Z)) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C48H83N3O15P2 |
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Average Molecular Weight | 1004.146 |
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Monoisotopic Molecular Weight | 1003.529942981 |
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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}({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]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([hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)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/C\C=C/CCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C48H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h11,13,17-20,35-36,40-41,45-47,54-55H,3-10,12,14-16,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b13-11-,19-17-,20-18-/t40-,41-,45+,46?,47-/m1/s1 |
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InChI Key | QFEGCLBTFDLZOL-RHKCEWHWSA-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(16:0/16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027008)
- Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027185)
- Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027241)
- Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027284)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027557)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027666)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027714)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0027751)
- Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028053)
- Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028132)
- Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028184)
- Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028224)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028438)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028478)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028519)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028560)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028626)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028691)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028730)
- Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028771)
- Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028818)
- Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028864)
- Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028903)
- Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028933)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028964)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028995)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029051)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029106)
- Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029135)
- Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029166)
- Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029203)
- Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029239)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029270)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029292)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029315)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029340)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0) (PathBank: SMP0029364)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0029365)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0) (PathBank: SMP0029366)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z)) (PathBank: SMP0029367)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029368)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0029369)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029370)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029371)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029372)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029373)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0029374)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0029375)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0029376)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029377)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0029378)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0029379)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0029380)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029381)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029382)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029383)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029384)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029385)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029386)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029387)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029388)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029389)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029390)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029391)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029403)
- Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029566)
- Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029568)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0029935)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0030103)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0030205)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0030214)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0030217)
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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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