Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-09 16:08:02 UTC |
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Update Date | 2019-07-23 07:15:24 UTC |
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HMDB ID | HMDB0060932 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Desmethyl sildenafil (UK-103,320) |
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Description | N-Desmethyl sildenafil (UK-103 320) is a metabolite of sildenafil. Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It was originally developed by British scientists and then brought to market by the US-based pharmaceutical company Pfizer. It acts by inhibiting cGMP-specific phosphodiesterase type 5, an enzyme that promotes degradation of cGMP, which regulates blood flow in the penis. (Wikipedia) |
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Structure | CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1 InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28) |
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Synonyms | Value | Source |
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Citrate, sildenafil | HMDB | Desmethyl sildenafil | HMDB | Sildenafil lactate | HMDB | 1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrate | HMDB | Lactate, sildenafil | HMDB | NCX-911 | HMDB | Nitrate, sildenafil | HMDB | Revatio | HMDB | Viagra | HMDB | Acetildenafil | HMDB | Sildenafil citrate | HMDB | Sildenafil, desmethyl | HMDB | Hydroxyhomosildenafil | HMDB | NCX 911 | HMDB | Homosildenafil | HMDB | Sildenafil | HMDB | Sildenafil nitrate | HMDB | 5-[2-Ethoxy-5-(piperazine-1-sulphonyl)phenyl]-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-D]pyrimidin-7-one | Generator |
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Chemical Formula | C21H28N6O4S |
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Average Molecular Weight | 460.55 |
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Monoisotopic Molecular Weight | 460.189274104 |
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IUPAC Name | 5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one |
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Traditional Name | 5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one |
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CAS Registry Number | Not Available |
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SMILES | CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1 |
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InChI Identifier | InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28) |
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InChI Key | UZTKBZXHEOVDRL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzenesulfonamides |
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Direct Parent | Benzenesulfonamides |
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Alternative Parents | |
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Substituents | - Benzenesulfonamide
- Pyrazolopyrimidine
- Benzenesulfonyl group
- Phenoxy compound
- Phenol ether
- Alkyl aryl ether
- Pyrimidone
- Pyrimidine
- 1,4-diazinane
- Organosulfonic acid amide
- Piperazine
- Sulfonyl
- Azole
- Organosulfonic acid or derivatives
- Vinylogous amide
- Pyrazole
- Organic sulfonic acid or derivatives
- Heteroaromatic compound
- Secondary aliphatic amine
- Ether
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic oxide
- Organic nitrogen compound
- Organosulfur compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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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N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 3810.6 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 3842.0 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 5788.9 | Standard polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4007.4 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 3940.5 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 5666.6 | Standard polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 3994.3 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4063.9 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C)CC3)=CC=C1OCC)=NC2=O | 5282.9 | Standard polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 3930.5 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 4112.9 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCNCC3)=CC=C1OCC)=NC2=O | 5655.7 | Standard polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4178.3 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4178.3 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),1TBDMS,isomer #2 | CCCC1=NN(C)C2=C1[NH]C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 5709.4 | Standard polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4276.6 | Semi standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 4550.5 | Standard non polar | 33892256 | N-Desmethyl sildenafil (UK-103,320),2TBDMS,isomer #1 | CCCC1=NN(C)C2=C1N([Si](C)(C)C(C)(C)C)C(C1=CC(S(=O)(=O)N3CCN([Si](C)(C)C(C)(C)C)CC3)=CC=C1OCC)=NC2=O | 5266.9 | 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 - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, Positive | splash10-06su-9003200000-8c16e5a5f7c9fd1beeec | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 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 - N-Desmethyl sildenafil (UK-103,320) 10V, Positive-QTOF | splash10-03di-0002900000-f0e3e78187afd93a4841 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Positive-QTOF | splash10-03dr-3235900000-dd447bbc8e39fc99d123 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Positive-QTOF | splash10-014u-5092100000-0b6e7602ec4d55ff9d63 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 10V, Negative-QTOF | splash10-0a4i-0000900000-f84c25238b265817528b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 20V, Negative-QTOF | splash10-053s-0303900000-1fb03e95cc836e9368b4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Desmethyl sildenafil (UK-103,320) 40V, Negative-QTOF | splash10-0002-9716200000-b08598b77f5c8dcf3abf | 2017-10-06 | Wishart Lab | View Spectrum |
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