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 06:44:21 UTC |
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Update Date | 2022-11-30 19:26:26 UTC |
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HMDB ID | HMDB0116020 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) |
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Description | CDP-DG(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 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(22:5(7Z,10Z,13Z,16Z,19Z)/16:0), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of palmitic 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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-45(54)63-39-42(66-46(55)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2)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/h5,7,11,13,17-18,20-21,24-25,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,14-16,19,22-23,26-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,13-11-,18-17-,21-20-,25-24-/t42-,43-,47+,48?,49-/m1/s1 |
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Synonyms | Value | Source |
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1-clupanodonoyl-2-palmitoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-clupanodonoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(22:5/16:0) | SMPDB, HMDB | CDP-DG(22:5n3/16:0) | SMPDB, HMDB | CDP-DG(22:5w3/16:0) | SMPDB, HMDB | CDP-DG(38:5) | SMPDB, HMDB | CDP-diacylglycerol(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | SMPDB, HMDB | CDP-diacylglycerol(22:5/16:0) | SMPDB, HMDB | CDP-diacylglycerol(22:5n3/16:0) | SMPDB, HMDB | CDP-diacylglycerol(22:5w3/16:0) | SMPDB, HMDB | CDP-diacylglycerol(38:5) | SMPDB, HMDB | CDP-DG(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-3-[(7Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinate | Generator, HMDB |
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Chemical Formula | C50H83N3O15P2 |
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Average Molecular Weight | 1028.168 |
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Monoisotopic Molecular Weight | 1027.529942981 |
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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}({[(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)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)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-45(54)63-39-42(66-46(55)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2)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/h5,7,11,13,17-18,20-21,24-25,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,14-16,19,22-23,26-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,13-11-,18-17-,21-20-,25-24-/t42-,43-,47+,48?,49-/m1/s1 |
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InChI Key | LFSDPCOXUIEYPT-PYMDQYKNSA-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(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0069528)
- Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027034)
- Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027094)
- Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027141)
- Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027196)
- Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027252)
- Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027297)
- Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027339)
- Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027385)
- Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027437)
- Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027476)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027518)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027583)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027838)
- 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(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0027960)
- Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028318)
- Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028366)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028449)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028586)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028652)
- Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028790)
- Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028837)
- Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0028914)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029021)
- Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029077)
- Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029185)
- Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029222)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029283)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029432)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029495)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029525)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029590)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029717)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029752)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029778)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029832)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029854)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029877)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029898)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029919)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029941)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029959)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029976)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029999)
- Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0030020)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0030040)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0030041)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0030042)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0030043)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0030044)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0030045)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0030046)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0030047)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030048)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030049)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0030050)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0030051)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030052)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030053)
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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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