Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 20:55:26 UTC |
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Updated at | 2024-09-11 20:55:26 UTC |
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NP-MRD ID | NP0339294 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | PGP(18:0/16:0) |
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Description | PGP(18:0/16:0), Also known as PGP(34:0), Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. PGP(18:0/16:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). PGP(18:0/16:0) Is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). Fatty acids containing 16, 18 and 20 carbons are the most common. PGP also serves as a precursor for the synthesis of cardiolipin. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. |
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Structure | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C40H80O13P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(42)49-35-38(36-52-55(47,48)51-34-37(41)33-50-54(44,45)46)53-40(43)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41H,3-36H2,1-2H3,(H,47,48)(H2,44,45,46)/t37-,38+/m0/s1 |
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Synonyms | Value | Source |
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1-Stearoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | HMDB | 3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | HMDB | PGP(34:0) | HMDB | 1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | HMDB | PGP(18:0/16:0) | Lipid Annotator |
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Chemical Formula | C40H80O13P2 |
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Average Mass | 831.0150 Da |
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Monoisotopic Mass | 830.50742 Da |
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IUPAC Name | [(2S)-3-({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid |
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Traditional Name | (2S)-3-{[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C40H80O13P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(42)49-35-38(36-52-55(47,48)51-34-37(41)33-50-54(44,45)46)53-40(43)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h37-38,41H,3-36H2,1-2H3,(H,47,48)(H2,44,45,46)/t37-,38+/m0/s1 |
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InChI Key | XHQRSMDNNVZHKZ-QPPIDDCLSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. |
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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 | Glycerophosphoglycerophosphates |
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Direct Parent | Phosphatidylglycerophosphates |
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Alternative Parents | |
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Substituents | - Diacylglycerophosphoglycerophosphate
- Sn-glycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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