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 07:27:49 UTC |
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Update Date | 2022-11-30 19:26:31 UTC |
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HMDB ID | HMDB0116223 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(i-16:0/18:2(9Z,11Z)) |
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Description | CDP-DG(i-16:0/18:2(9Z,11Z)) 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(i-16:0/18:2(9Z,11Z)), in particular, consists of one chain of isohexadecanoic acid at the C-1 position and one chain of (9Z,11Z)-octadecadienoic 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)CCCCCCCCCCCCC(C)C)(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/C=C\CCCCCC InChI=1S/C46H81N3O15P2/c1-4-5-6-7-8-9-10-11-12-13-14-19-22-25-28-31-42(51)62-38(34-59-41(50)30-27-24-21-18-16-15-17-20-23-26-29-37(2)3)35-60-65(55,56)64-66(57,58)61-36-39-43(52)44(53)45(63-39)49-33-32-40(47)48-46(49)54/h9-12,32-33,37-39,43-45,52-53H,4-8,13-31,34-36H2,1-3H3,(H,55,56)(H,57,58)(H2,47,48,54)/b10-9-,12-11-/t38-,39-,43+,44?,45-/m1/s1 |
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Synonyms | Value | Source |
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1-Isohexadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-CDP | HMDB | 1-Isohexadecanoyl-2-(9Z,11Z)-octadecadienoyl-sn-glycero-3-cytidine-5'-diphosphate | HMDB | CDP-DG(I-16:0/18:2) | HMDB | CDP-DG(I-16:0/18:2N7) | HMDB | CDP-DG(I-16:0/18:2W7) | HMDB | CDP-DG(34:2) | HMDB | CDP-Diacylglycerol(I-16:0/18:2(9Z,11Z)) | HMDB | CDP-Diacylglycerol(I-16:0/18:2) | HMDB | CDP-Diacylglycerol(I-16:0/18:2N7) | HMDB | CDP-Diacylglycerol(I-16:0/18:2W7) | HMDB | CDP-Diacylglycerol(34:2) | HMDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-[(14-methylpentadecanoyl)oxy]-2-[(9Z,11Z)-octadeca-9,11-dienoyloxy]propoxy]phosphoryl}oxy)phosphinate | HMDB | CDP-DG(i-16:0/18:2(9Z,11Z)) | SMPDB |
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Chemical Formula | C46H81N3O15P2 |
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Average Molecular Weight | 978.108 |
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Monoisotopic Molecular Weight | 977.514292916 |
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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}({hydroxy[(2R)-3-[(14-methylpentadecanoyl)oxy]-2-[(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)-3-[(14-methylpentadecanoyl)oxy]-2-[(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)CCCCCCCCCCCCC(C)C)(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/C=C\CCCCCC |
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InChI Identifier | InChI=1S/C46H81N3O15P2/c1-4-5-6-7-8-9-10-11-12-13-14-19-22-25-28-31-42(51)62-38(34-59-41(50)30-27-24-21-18-16-15-17-20-23-26-29-37(2)3)35-60-65(55,56)64-66(57,58)61-36-39-43(52)44(53)45(63-39)49-33-32-40(47)48-46(49)54/h9-12,32-33,37-39,43-45,52-53H,4-8,13-31,34-36H2,1-3H3,(H,55,56)(H,57,58)(H2,47,48,54)/b10-9-,12-11-/t38-,39-,43+,44?,45-/m1/s1 |
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InChI Key | QAJXPUFSYJMJJJ-IINMTLQDSA-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-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0044146)
- Cardiolipin Biosynthesis CL(a-13:0/i-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0047048)
- Cardiolipin Biosynthesis CL(a-13:0/i-20:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0048013)
- Cardiolipin Biosynthesis CL(i-12:0/a-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0050271)
- Cardiolipin Biosynthesis CL(i-12:0/i-12:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0051242)
- Cardiolipin Biosynthesis CL(i-12:0/i-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0052212)
- Cardiolipin Biosynthesis CL(i-12:0/i-16:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0052534)
- Cardiolipin Biosynthesis CL(i-12:0/i-19:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0053504)
- Cardiolipin Biosynthesis CL(i-13:0/a-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0056090)
- Cardiolipin Biosynthesis CL(i-13:0/a-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0056414)
- Cardiolipin Biosynthesis CL(i-13:0/i-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0060021)
- Cardiolipin Biosynthesis CL(i-14:0/a-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0061009)
- Cardiolipin Biosynthesis CL(i-14:0/i-12:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0061826)
- Cardiolipin Biosynthesis CL(i-14:0/i-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0062801)
- Cardiolipin Biosynthesis CL(i-14:0/i-16:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0063135)
- Cardiolipin Biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0043501)
- Cardiolipin Biosynthesis CL(a-13:0/a-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0043823)
- Cardiolipin Biosynthesis CL(a-13:0/i-12:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0045436)
- Cardiolipin Biosynthesis CL(a-13:0/i-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0046402)
- Cardiolipin Biosynthesis CL(a-13:0/i-18:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0047369)
- Cardiolipin Biosynthesis CL(i-12:0/a-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0049625)
- Cardiolipin Biosynthesis CL(i-12:0/a-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0050593)
- Cardiolipin Biosynthesis CL(i-12:0/a-25:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0050917)
- Cardiolipin Biosynthesis CL(i-12:0/i-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0051566)
- Cardiolipin Biosynthesis CL(i-12:0/i-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0054151)
- Cardiolipin Biosynthesis CL(i-12:0/i-24:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0054794)
- Cardiolipin Biosynthesis CL(i-13:0/i-14:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0057719)
- Cardiolipin Biosynthesis CL(i-13:0/i-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0058686)
- Cardiolipin Biosynthesis CL(i-13:0/i-18:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0059029)
- Cardiolipin Biosynthesis CL(i-14:0/a-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0061335)
- Cardiolipin Biosynthesis CL(i-14:0/i-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0063408)
- Cardiolipin Biosynthesis CL(a-13:0/i-14:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0046078)
- Cardiolipin Biosynthesis CL(a-13:0/i-16:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0046724)
- Cardiolipin Biosynthesis CL(i-12:0/a-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0049947)
- Cardiolipin Biosynthesis CL(i-12:0/i-18:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0053181)
- Cardiolipin Biosynthesis CL(i-12:0/i-20:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0053826)
- Cardiolipin Biosynthesis CL(i-12:0/i-22:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0054473)
- Cardiolipin Biosynthesis CL(i-13:0/a-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0055443)
- Cardiolipin Biosynthesis CL(i-13:0/i-12:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0057064)
- Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0057386)
- Cardiolipin Biosynthesis CL(i-13:0/i-16:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0058365)
- Cardiolipin Biosynthesis CL(i-13:0/i-20:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0059684)
- Cardiolipin Biosynthesis CL(a-13:0/a-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0044467)
- Cardiolipin Biosynthesis CL(a-13:0/a-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0044791)
- Cardiolipin Biosynthesis CL(a-13:0/a-25:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0045114)
- Cardiolipin Biosynthesis CL(a-13:0/i-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0045756)
- Cardiolipin Biosynthesis CL(a-13:0/i-19:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0047692)
- Cardiolipin Biosynthesis CL(a-13:0/i-21:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0048333)
- Cardiolipin Biosynthesis CL(a-13:0/i-22:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0048657)
- Cardiolipin Biosynthesis CL(a-13:0/i-24:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0048979)
- Cardiolipin Biosynthesis CL(i-12:0/18:2(9Z,11Z)/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0049302)
- Cardiolipin Biosynthesis CL(i-12:0/i-14:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0051889)
- Cardiolipin Biosynthesis CL(i-12:0/i-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0052858)
- Cardiolipin Biosynthesis CL(i-13:0/18:2(9Z,11Z)/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0055118)
- Cardiolipin Biosynthesis CL(i-13:0/a-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0055766)
- Cardiolipin Biosynthesis CL(i-13:0/a-25:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0056741)
- Cardiolipin Biosynthesis CL(i-13:0/i-15:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0058043)
- Cardiolipin Biosynthesis CL(i-13:0/i-19:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0059359)
- Cardiolipin Biosynthesis CL(i-13:0/i-22:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0060359)
- Cardiolipin Biosynthesis CL(i-13:0/i-24:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0060681)
- Cardiolipin Biosynthesis CL(i-14:0/a-17:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0061608)
- Cardiolipin Biosynthesis CL(i-14:0/i-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0062149)
- Cardiolipin Biosynthesis CL(i-14:0/i-14:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0062472)
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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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