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 18:59:27 UTC |
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Update Date | 2019-07-23 07:15:06 UTC |
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HMDB ID | HMDB0060788 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 6-O-Desmethyl-mycophenolic acid |
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Description | 6-O-Desmethyl-mycophenolic acid belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 6-O-Desmethyl-mycophenolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-O-Desmethyl-mycophenolic acid is a metabolite of mycophenolic acid. It inhibits an enzyme needed for the growth of T cells and B cells. 6-O-desmethyl-mycophenolic acid and formaldehyde can be biosynthesized from mycophenolic acid; which is catalyzed by the enzymes cytochrome P450 3A4, cytochrome P450 3A5, and cytochrome P450 2C8. In humans, 6-O-desmethyl-mycophenolic acid is involved in mycophenolic acid metabolism pathway. It was initially marketed as the prodrug mycophenolate mofetil (MMF) to improve oral bioavailability. Mycophenolic acid or mycophenolate is an immunosuppressant drug used to prevent rejection in organ transplantation. Mycophenolic acid is commonly marketed under the trade names CellCept and Myfortic. More recently, the salt mycophenolate sodium has also been introduced. |
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Structure | CC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O InChI=1S/C16H18O6/c1-8(4-6-12(17)18)3-5-10-14(19)9(2)11-7-22-16(21)13(11)15(10)20/h3,19-20H,4-7H2,1-2H3,(H,17,18) |
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Synonyms | Value | Source |
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6-O-Desmethyl-mycophenolate | Generator |
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Chemical Formula | C16H18O6 |
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Average Molecular Weight | 306.3105 |
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Monoisotopic Molecular Weight | 306.110338308 |
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IUPAC Name | 6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid |
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Traditional Name | 6-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(CCC(O)=O)=CCC1=C(O)C(C)=C2COC(=O)C2=C1O |
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InChI Identifier | InChI=1S/C16H18O6/c1-8(4-6-12(17)18)3-5-10-14(19)9(2)11-7-22-16(21)13(11)15(10)20/h3,19-20H,4-7H2,1-2H3,(H,17,18) |
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InChI Key | MHSRNZSBNXFMLF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. |
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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 | Benzoic acids and derivatives |
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Direct Parent | Hydroxybenzoic acid derivatives |
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Alternative Parents | |
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Substituents | - Dihydroxybenzoic acid
- Isobenzofuranone
- Phthalide
- Isocoumaran
- Medium-chain fatty acid
- Branched fatty acid
- Heterocyclic fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Unsaturated fatty acid
- Fatty acid
- Vinylogous acid
- Lactone
- Carboxylic acid ester
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- 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 | |
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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 | | Show more...
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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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6-O-Desmethyl-mycophenolic acid,1TMS,isomer #1 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O)CCC(=O)O[Si](C)(C)C | 2600.8 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,1TMS,isomer #2 | CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C)CCC(=O)O | 2664.1 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,1TMS,isomer #3 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O | 2660.4 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TMS,isomer #1 | CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C | 2668.7 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TMS,isomer #2 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C | 2657.4 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TMS,isomer #3 | CC(=CCC1=C(O[Si](C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O | 2718.2 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,3TMS,isomer #1 | CC(=CCC1=C(O[Si](C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C)CCC(=O)O[Si](C)(C)C | 2737.0 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #1 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O)CCC(=O)O[Si](C)(C)C(C)(C)C | 2818.2 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #2 | CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O | 2876.3 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,1TBDMS,isomer #3 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O | 2884.8 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #1 | CC(=CCC1=C(O)C2=C(COC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C | 3110.7 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #2 | CC(=CCC1=C(O)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C | 3104.4 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,2TBDMS,isomer #3 | CC(=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O | 3168.3 | Semi standard non polar | 33892256 | 6-O-Desmethyl-mycophenolic acid,3TBDMS,isomer #1 | CC(=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C2COC(=O)C2=C1O[Si](C)(C)C(C)(C)C)CCC(=O)O[Si](C)(C)C(C)(C)C | 3428.4 | Semi standard non polar | 33892256 |
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Spectra |
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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 - 6-O-Desmethyl-mycophenolic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-03ea-1190000000-c0f5cb5448f716834ad3 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid GC-MS (3 TMS) - 70eV, Positive | splash10-0a4i-4104790000-88b6dd1b7b4c2071e688 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 6-O-Desmethyl-mycophenolic acid 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 - 6-O-Desmethyl-mycophenolic acid 10V, Positive-QTOF | splash10-000i-0092000000-b9194ed275a421a8a796 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Positive-QTOF | splash10-03du-3490000000-1055c38862b60e2a5443 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Positive-QTOF | splash10-0gb9-9730000000-4a3915b3ffac607615da | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Negative-QTOF | splash10-0a4i-0069000000-e65af122fdd879e1678b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Negative-QTOF | splash10-0a4r-1093000000-51d47e208eeac0ebf63b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Negative-QTOF | splash10-0a4i-6390000000-964847eb7414adae072c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Positive-QTOF | splash10-0a4m-0987000000-770c963837f490cc31b8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Positive-QTOF | splash10-052f-2970000000-12469430d1cdcd28a9db | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Positive-QTOF | splash10-0kbr-1910000000-7e35599874d5a204bc4b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 10V, Negative-QTOF | splash10-0a4i-0009000000-a4e78f227e456dc4b2b0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 20V, Negative-QTOF | splash10-0r29-1296000000-d3c43e0a118b2a36d397 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 6-O-Desmethyl-mycophenolic acid 40V, Negative-QTOF | splash10-014m-9660000000-a251ab7239f20c6b7c70 | 2021-10-12 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 57369640 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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