Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 15:12:24 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0002982 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Prostaglandin B1 |
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Description | Prostaglandin B1 (PGB1) is a metabolite of PGE1. PGE1 is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). PGB1does not inhibit phospholipase activity, but oligomers of PGB1 (PGBx) extracted from human neutrophils inhibit human phospholipases A2 in vitro and in situ in a dose-dependent manner; these oligomers inhibit arachidonic acid mobilization in human neutrophils and endothelial cells. One mechanism for the pharmacological effects of PGBx may be inhibition of cell-associated and extracellular phospholipase A2. PGB1 has the ability to enhance peripheral vascular resistance and elevate blood pressure. The effect is not central in origin and apparently is not the result of changes in cholinergic or alpha-adrenoceptor sensitivity or changes in vascular smooth muscle susceptibility per se. PGB1 blocks S-phase DNA synthesis; inhibition of DNA synthesis does not appear to require elevated levels of cAMP. (PMID: 7667505 , 1477202 , 2129000 , 2597672 , 6635328 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. |
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Structure | CCCCC[C@H](O)\C=C\C1=C(CCCCCCC(O)=O)C(=O)CC1 InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,17,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t17-/m0/s1 |
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Synonyms | Value | Source |
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PGB1 | ChEBI | (13E,15S)-15-Hydroxy-9-oxoprosta-8(12),13-dien-1-Oate | HMDB | (13E,15S)-15-Hydroxy-9-oxoprosta-8(12),13-dien-1-Oic acid | HMDB | 9-oxo-15S-Hydroxy-8(12),13E-prostadienoate | HMDB | 9-oxo-15S-Hydroxy-8(12),13E-prostadienoic acid | HMDB | Prostaglandin-b1 | HMDB | Prostaglandin b1 | MeSH |
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Chemical Formula | C20H32O4 |
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Average Molecular Weight | 336.4657 |
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Monoisotopic Molecular Weight | 336.230059512 |
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IUPAC Name | 7-{2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}heptanoic acid |
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Traditional Name | prostaglandin-B1 |
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CAS Registry Number | 13345-51-2 |
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SMILES | CCCCC[C@H](O)\C=C\C1=C(CCCCCCC(O)=O)C(=O)CC1 |
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InChI Identifier | InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,17,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t17-/m0/s1 |
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InChI Key | YBHMPNRDOVPQIN-VSOYFRJCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Prostaglandins and related compounds |
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Alternative Parents | |
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Substituents | - Prostaglandin skeleton
- Long-chain fatty acid
- Fatty alcohol
- Hydroxy fatty acid
- Ketone
- Cyclic ketone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Prostaglandin B1,1TMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O)C(=O)CC1)O[Si](C)(C)C | 2842.5 | Semi standard non polar | 33892256 | Prostaglandin B1,1TMS,isomer #2 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(=O)CC1 | 2775.4 | Semi standard non polar | 33892256 | Prostaglandin B1,1TMS,isomer #3 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O)C(O[Si](C)(C)C)=CC1 | 2856.8 | Semi standard non polar | 33892256 | Prostaglandin B1,2TMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(=O)CC1)O[Si](C)(C)C | 2824.3 | Semi standard non polar | 33892256 | Prostaglandin B1,2TMS,isomer #2 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C | 2893.2 | Semi standard non polar | 33892256 | Prostaglandin B1,2TMS,isomer #3 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1 | 2850.0 | Semi standard non polar | 33892256 | Prostaglandin B1,3TMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C | 2891.3 | Semi standard non polar | 33892256 | Prostaglandin B1,3TMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C | 2777.3 | Standard non polar | 33892256 | Prostaglandin B1,3TMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C | 3072.4 | Standard polar | 33892256 | Prostaglandin B1,1TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O)C(=O)CC1)O[Si](C)(C)C(C)(C)C | 3066.9 | Semi standard non polar | 33892256 | Prostaglandin B1,1TBDMS,isomer #2 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC1 | 3012.4 | Semi standard non polar | 33892256 | Prostaglandin B1,1TBDMS,isomer #3 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC1 | 3092.8 | Semi standard non polar | 33892256 | Prostaglandin B1,2TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC1)O[Si](C)(C)C(C)(C)C | 3316.0 | Semi standard non polar | 33892256 | Prostaglandin B1,2TBDMS,isomer #2 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C | 3345.6 | Semi standard non polar | 33892256 | Prostaglandin B1,2TBDMS,isomer #3 | CCCCC[C@H](O)/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1 | 3301.0 | Semi standard non polar | 33892256 | Prostaglandin B1,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C | 3571.5 | Semi standard non polar | 33892256 | Prostaglandin B1,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C | 3171.7 | Standard non polar | 33892256 | Prostaglandin B1,3TBDMS,isomer #1 | CCCCC[C@@H](/C=C/C1=C(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C | 3277.1 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Prostaglandin B1 GC-MS (Non-derivatized) - 70eV, Positive | splash10-05n0-5192000000-a7e9f36e25137b9fabcc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prostaglandin B1 GC-MS (2 TMS) - 70eV, Positive | splash10-010c-9126300000-342d7eee52879bb192e6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Prostaglandin B1 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 10V, Positive-QTOF | splash10-0gb9-0029000000-0690d2f3dfb5d1ee9afe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 20V, Positive-QTOF | splash10-0l6u-4495000000-96548847dc77e5ecb0dd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 40V, Positive-QTOF | splash10-06du-9230000000-bdbc4c091593478de78b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 10V, Negative-QTOF | splash10-000i-0019000000-af954838d61275b1a6b2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 20V, Negative-QTOF | splash10-014r-2059000000-e381e90f103a41486292 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 40V, Negative-QTOF | splash10-0a4l-9140000000-c082f378971a61d35c10 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 10V, Positive-QTOF | splash10-0uxr-0129000000-2d428b3ff47d60ebed59 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 20V, Positive-QTOF | splash10-0uy0-6797000000-9e0090cf284a26438dc4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 40V, Positive-QTOF | splash10-0api-9400000000-79d7c252855e7c736ea6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 10V, Negative-QTOF | splash10-014i-0029000000-877d392a3ea777176963 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 20V, Negative-QTOF | splash10-00ri-1297000000-51af315e563050950d6d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Prostaglandin B1 40V, Negative-QTOF | splash10-05tn-5930000000-05a9fe2c2833996f0a2a | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Hishinuma T, Nakamura H, Itoh K, Ohyama Y, Ishibashi M, Mizugaki M: Microdetermination of the prostaglandin B1 in human plasma by gas chromatography/selected ion monitoring using [18O]prostaglandin B1 as an internal standard. Prostaglandins. 1995 Apr;49(4):239-46. [PubMed:7667505 ]
- Fry MR, Ghosh SS, East JM, Franson RC: Role of human sperm phospholipase A2 in fertilization: effects of a novel inhibitor of phospholipase A2 activity on membrane perturbations and oocyte penetration. Biol Reprod. 1992 Nov;47(5):751-9. [PubMed:1477202 ]
- Franson R, Raghupathi R, Fry M, Saal J, Vishwanath B, Ghosh SS, Rosenthal MD: Inhibition of human phospholipases A2 by cis-unsaturated fatty acids and oligomers of prostaglandin B1. Adv Exp Med Biol. 1990;279:219-30. [PubMed:2129000 ]
- Franson RC, Rosenthal MD: Oligomers of prostaglandin B1 inhibit in vitro phospholipase A2 activity. Biochim Biophys Acta. 1989 Dec 18;1006(3):272-7. [PubMed:2597672 ]
- Himori N, Burkman AM: Prostaglandin B1 can modify the pressor responses to sympathetic nerve stimulation. Res Commun Chem Pathol Pharmacol. 1983 Sep;41(3):397-405. [PubMed:6635328 ]
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