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 06:33:07 UTC |
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Update Date | 2022-11-30 19:26:24 UTC |
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HMDB ID | HMDB0115959 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CDP-DG(18:1(11Z)/16:1(9Z)) |
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Description | CDP-DG(18:1(11Z)/16:1(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(18:1(11Z)/16:1(9Z)), in particular, consists of one chain of cis-vaccenic acid at the C-1 position and one chain of palmitoleic 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)CCCCCCCCC\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)CCCCCCC\C=C/CCCCCC InChI=1S/C46H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h13-16,33-34,38-39,43-45,52-53H,3-12,17-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b15-13-,16-14-/t38-,39-,43+,44?,45-/m1/s1 |
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Synonyms | Value | Source |
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1-cis-vaccenoyl-2-palmitoleoyl-sn-glycero-3-CDP | SMPDB, HMDB | 1-cis-vaccenoyl-2-palmitoleoyl-sn-glycero-3-cytidine-5'-diphosphate | SMPDB, HMDB | CDP-DG(18:1/16:1) | SMPDB, HMDB | CDP-DG(18:1n7/16:1n7) | SMPDB, HMDB | CDP-DG(18:1w7/16:1w7) | SMPDB, HMDB | CDP-DG(34:2) | SMPDB, HMDB | CDP-diacylglycerol(18:1(11Z)/16:1(9Z)) | SMPDB, HMDB | CDP-diacylglycerol(18:1/16:1) | SMPDB, HMDB | CDP-diacylglycerol(18:1n7/16:1n7) | SMPDB, HMDB | CDP-diacylglycerol(18:1w7/16:1w7) | SMPDB, HMDB | CDP-diacylglycerol(34:2) | SMPDB, HMDB | CDP-DG(18:1(11Z)/16:1(9Z)) | SMPDB | {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinate | Generator, HMDB |
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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}({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-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-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-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)CCCCCCCCC\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)CCCCCCC\C=C/CCCCCC |
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InChI Identifier | InChI=1S/C46H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h13-16,33-34,38-39,43-45,52-53H,3-12,17-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b15-13-,16-14-/t38-,39-,43+,44?,45-/m1/s1 |
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InChI Key | ULTWNYMRCNQYCB-HOXHGPEGSA-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(16:0/16:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0026985)
- Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027077)
- Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027164)
- Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027220)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027501)
- Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027534)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027612)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027645)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027693)
- Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027739)
- Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027775)
- Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027810)
- 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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027897)
- Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0027985)
- Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028030)
- Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028111)
- Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028163)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028417)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028458)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z)) (PathBank: SMP0028459)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z)) (PathBank: SMP0028460)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0028461)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028462)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028463)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028464)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028465)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0) (PathBank: SMP0028466)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)) (PathBank: SMP0028467)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0) (PathBank: SMP0028468)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z)) (PathBank: SMP0028469)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z)) (PathBank: SMP0028470)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)) (PathBank: SMP0028471)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028472)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028473)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028474)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028475)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)) (PathBank: SMP0028476)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0028477)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0028478)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0028479)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0028480)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0028481)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0028482)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0028483)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0028484)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0028485)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0028486)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028487)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028488)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0028489)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028490)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028491)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0028492)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028493)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0028494)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0028495)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0028496)
- Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0028497)
- Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0028498)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0029336)
- 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)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0029393)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z)) (PathBank: SMP0030197)
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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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