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 06:51:40 UTC |
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Update Date | 2022-11-30 19:26:27 UTC |
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HMDB ID | HMDB0116059 |
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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,11Z)/i-19:0) |
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Description | CDP-DG(18:2(9Z,11Z)/i-19:0) 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(18:2(9Z,11Z)/i-19:0), in particular, consists of one chain of (9Z,11Z)-octadecadienoic acid at the C-1 position and one chain of isononadecanoic 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\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)CCCCCCCCCCCCCCCC(C)C InChI=1S/C49H87N3O15P2/c1-4-5-6-7-8-9-10-11-12-15-18-21-24-27-30-33-44(53)62-37-41(65-45(54)34-31-28-25-22-19-16-13-14-17-20-23-26-29-32-40(2)3)38-63-68(58,59)67-69(60,61)64-39-42-46(55)47(56)48(66-42)52-36-35-43(50)51-49(52)57/h9-12,35-36,40-42,46-48,55-56H,4-8,13-34,37-39H2,1-3H3,(H,58,59)(H,60,61)(H2,50,51,57)/b10-9-,12-11-/t41-,42-,46+,47?,48-/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z,11Z)-Octadecadienoyl-2-isononadecanoyl-sn-glycero-3-CDP | HMDB | 1-(9Z,11Z)-Octadecadienoyl-2-isononadecanoyl-sn-glycero-3-cytidine-5'-diphosphate | HMDB | CDP-DG(18:2/I-19:0) | HMDB | CDP-DG(18:2N7/I-19:0) | HMDB | CDP-DG(18:2W7/I-19:0) | HMDB | CDP-DG(37:2) | HMDB | CDP-Diacylglycerol(18:2(9Z,11Z)/I-19:0) | HMDB | CDP-Diacylglycerol(18:2/I-19:0) | HMDB | CDP-Diacylglycerol(18:2N7/I-19:0) | HMDB | CDP-Diacylglycerol(18:2W7/I-19:0) | HMDB | CDP-Diacylglycerol(37:2) | HMDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(17-methyloctadecanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | HMDB | CDP-DG(18:2(9Z,11Z)/i-19:0) | SMPDB |
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Chemical Formula | C49H87N3O15P2 |
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Average Molecular Weight | 1020.189 |
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Monoisotopic Molecular Weight | 1019.561243109 |
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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-[(17-methyloctadecanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-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-[(17-methyloctadecanoyl)oxy]-3-[(9Z,11Z)-octadeca-9,11-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\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)CCCCCCCCCCCCCCCC(C)C |
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InChI Identifier | InChI=1S/C49H87N3O15P2/c1-4-5-6-7-8-9-10-11-12-15-18-21-24-27-30-33-44(53)62-37-41(65-45(54)34-31-28-25-22-19-16-13-14-17-20-23-26-29-32-40(2)3)38-63-68(58,59)67-69(60,61)64-39-42-46(55)47(56)48(66-42)52-36-35-43(50)51-49(52)57/h9-12,35-36,40-42,46-48,55-56H,4-8,13-34,37-39H2,1-3H3,(H,58,59)(H,60,61)(H2,50,51,57)/b10-9-,12-11-/t41-,42-,46+,47?,48-/m1/s1 |
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InChI Key | CSSVOKRJQPIPSZ-PXKAAIOPSA-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
- Fatty acid ester
- Monoalkyl phosphate
- Hydroxypyrimidine
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Hydropyrimidine
- Pyrimidine
- Phosphoric acid ester
- Monosaccharide
- Organic phosphoric acid derivative
- Heteroaromatic compound
- Tetrahydrofuran
- Carboxylic acid ester
- 1,2-diol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Organopnictogen compound
- Organic oxide
- Alcohol
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- 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 | |
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Process | Naturally occurring processBiological processBiochemical pathwayDisease pathway- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0044624)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0045271)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0050750)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0053660)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0053984)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0054951)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0055921)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0056247)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0057875)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0060185)
- Cardiolipin Biosynthesis CL(a-13:0/a-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0043980)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0044302)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0044947)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0045592)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0046558)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0048168)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0048813)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0049136)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0049780)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0050104)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0050427)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0052691)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0055275)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0058520)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0058850)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0059515)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0061167)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0062968)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0045911)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0047204)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0047526)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0048491)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0049459)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0051075)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0051399)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0052045)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0053337)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0054307)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0054629)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0056573)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0056898)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0058200)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0059191)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0061660)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0061982)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0062305)
- Cardiolipin Biosynthesis CL(a-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0043335)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0043657)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0046235)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0046881)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0047849)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0051723)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0052368)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0053014)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0055599)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0057219)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0057542)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0059850)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0060515)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0060843)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0062633)
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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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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