Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 19:04:56 UTC |
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Update Date | 2019-07-23 07:15:16 UTC |
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HMDB ID | HMDB0060873 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sorafenib N-oxide |
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Description | Sorafenib N-oxide, also known as sorafenib or nexavar, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Sorafenib N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). sorafenib N-oxide can be biosynthesized from sorafenib through the action of the enzyme cytochrome P450 3A4. In humans, sorafenib N-oxide is involved in sorafenib metabolism pathway. |
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Structure | CNC(=O)C1=[N+]([O-])C=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(=C3)C(F)(F)F)C=C2)=C1 InChI=1S/C21H16ClF3N4O4/c1-26-19(30)18-11-15(8-9-29(18)32)33-14-5-2-12(3-6-14)27-20(31)28-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,27,28,31) |
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Synonyms | Value | Source |
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Nexavar | HMDB | 4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxyllic acid methyamide-4-methylbenzenesulfonate | HMDB | Sorafenib | HMDB | Sorafenib tosylate | HMDB | 4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxylic acid methyamide-4-methylbenzenesulfonate | MeSH | Sorafenib N oxide | MeSH |
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Chemical Formula | C21H16ClF3N4O4 |
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Average Molecular Weight | 480.824 |
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Monoisotopic Molecular Weight | 480.081217342 |
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IUPAC Name | 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-2-(methylcarbamoyl)pyridin-1-ium-1-olate |
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Traditional Name | 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-2-(methylcarbamoyl)pyridin-1-ium-1-olate |
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CAS Registry Number | Not Available |
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SMILES | CNC(=O)C1=[N+]([O-])C=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(=C3)C(F)(F)F)C=C2)=C1 |
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InChI Identifier | InChI=1S/C21H16ClF3N4O4/c1-26-19(30)18-11-15(8-9-29(18)32)33-14-5-2-12(3-6-14)27-20(31)28-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,27,28,31) |
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InChI Key | BQAZCCVUZDIZDC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Ethers |
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Direct Parent | Diarylethers |
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Alternative Parents | |
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Substituents | - Diaryl ether
- N-phenylurea
- Trifluoromethylbenzene
- Pyridine carboxylic acid or derivatives
- 2-heteroaryl carboxamide
- Phenoxy compound
- Phenol ether
- Chlorobenzene
- Halobenzene
- Benzenoid
- Pyridinium
- Pyridine
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Heteroaromatic compound
- Urea
- Secondary carboxylic acid amide
- Carboxamide group
- Carbonic acid derivative
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Organic zwitterion
- Organopnictogen compound
- Alkyl halide
- Organic nitrogen compound
- Alkyl fluoride
- Organohalogen compound
- Organochloride
- Carbonyl group
- Organofluoride
- Organonitrogen compound
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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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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Sorafenib N-oxide,1TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3972.8 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3371.5 | Standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 4341.6 | Standard polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3686.1 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3299.3 | Standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 4293.7 | Standard polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3716.6 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3306.4 | Standard non polar | 33892256 | Sorafenib N-oxide,1TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 4363.8 | Standard polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3738.9 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3208.1 | Standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3934.0 | Standard polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3765.4 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3191.2 | Standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 4017.8 | Standard polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3508.9 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3184.1 | Standard non polar | 33892256 | Sorafenib N-oxide,2TMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-] | 3932.7 | Standard polar | 33892256 | Sorafenib N-oxide,3TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3596.5 | Semi standard non polar | 33892256 | Sorafenib N-oxide,3TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3133.4 | Standard non polar | 33892256 | Sorafenib N-oxide,3TMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C)[Si](C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C | 3688.5 | Standard polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4218.8 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 3538.9 | Standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4375.6 | Standard polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3906.4 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3464.0 | Standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #2 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 4276.2 | Standard polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3938.7 | Semi standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3461.3 | Standard non polar | 33892256 | Sorafenib N-oxide,1TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 4347.7 | Standard polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4198.1 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 3519.7 | Standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)NC3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4024.3 | Standard polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4224.4 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 3507.3 | Standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #2 | CN(C(=O)C1=CC(OC2=CC=C(NC(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4110.0 | Standard polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3932.4 | Semi standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 3505.7 | Standard non polar | 33892256 | Sorafenib N-oxide,2TBDMS,isomer #3 | CNC(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-] | 4005.5 | Standard polar | 33892256 | Sorafenib N-oxide,3TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 4245.7 | Semi standard non polar | 33892256 | Sorafenib N-oxide,3TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 3615.4 | Standard non polar | 33892256 | Sorafenib N-oxide,3TBDMS,isomer #1 | CN(C(=O)C1=CC(OC2=CC=C(N(C(=O)N(C3=CC=C(Cl)C(C(F)(F)F)=C3)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=CC=[N+]1[O-])[Si](C)(C)C(C)(C)C | 3890.6 | Standard polar | 33892256 |
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