Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-15 16:56:51 UTC |
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Update Date | 2021-09-14 15:39:04 UTC |
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HMDB ID | HMDB0060568 |
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Secondary Accession Numbers | - HMDB0060674
- HMDB60568
- HMDB60674
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Metabolite Identification |
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Common Name | 10,11-Dihydroxycarbamazepine |
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Description | 10,11-Dihydroxycarbamazepine, also called carbamazepine diol, is a metabolite of both carbamazepine and oxcarbazepine. Carbamazepine (CBZ) is an anticonvulsant and mood-stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder, as well as trigeminal neuralgia. Oxcarbazepine is an anticonvulsant and mood-stabilizing drug, used primarily in the treatment of epilepsy. It is also used to treat anxiety and mood disorders, and benign motor tics. (Wikipedia) |
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Structure | O[C@@H]1[C@@H](O)C2=CC=CC=C2N(C(O)=N)C2=CC=CC=C12 InChI=1S/C15H14N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,13-14,18-19H,(H2,16,20)/t13-,14-/m0/s1 |
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Synonyms | Value | Source |
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(-)-(S,S)-trans-10,11-Dihydro-10,11-dihydroxy-5H-dibenzo[b,F]azepine-5-carboxamide | ChEBI | 10,11-Dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide, (cis)-isomer | MeSH | 10,11-Dihydroxy-10,11-dihydrocarbamazepine | MeSH | 10,11-Dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide, (10S,trans)-isomer | MeSH | 10,11-Dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide, (trans)-isomer | MeSH | 10,11-Dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide, (trans-(+-))-isomer | MeSH | 10,11-Dihydro-10,11-dihydroxycarbamazepine | MeSH | Carbazepine 10,11-diol | MeSH | CBZ-Diol | MeSH | 10,11-Dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide | MeSH | 10,11-Dihydro-10,11-transdihydroxycarbamazepine | MeSH | CBZD | MeSH | Carbamazepine-10,11-diol | MeSH | Carbamazepine-10,11-transdiol | MeSH |
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Chemical Formula | C15H14N2O3 |
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Average Molecular Weight | 270.2833 |
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Monoisotopic Molecular Weight | 270.100442324 |
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IUPAC Name | (9S,10S)-9,10-dihydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboximidic acid |
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Traditional Name | (9S,10S)-9,10-dihydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboximidic acid |
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CAS Registry Number | Not Available |
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SMILES | O[C@@H]1[C@@H](O)C2=CC=CC=C2N(C(O)=N)C2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C15H14N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,13-14,18-19H,(H2,16,20)/t13-,14-/m0/s1 |
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InChI Key | PRGQOPPDPVELEG-KBPBESRZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzazepines |
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Sub Class | Dibenzazepines |
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Direct Parent | Dibenzazepines |
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Alternative Parents | |
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Substituents | - Dibenzazepine
- Azepine
- Benzenoid
- 1,2-diol
- Isourea
- Secondary alcohol
- Carboximidic acid derivative
- Azacycle
- Organonitrogen compound
- Hydrocarbon derivative
- Imine
- Organopnictogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | - 10,11-trans-dihydroxy-10,11-dihydrocarbamazepine (CHEBI:83815 )
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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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10,11-Dihydroxycarbamazepine,1TMS,isomer #1 | C[Si](C)(C)O[C@H]1C2=CC=CC=C2N(C(=N)O)C2=CC=CC=C2[C@@H]1O | 2453.4 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,1TMS,isomer #2 | C[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2413.7 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,1TMS,isomer #3 | C[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2417.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TMS,isomer #1 | C[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2416.9 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TMS,isomer #2 | C[Si](C)(C)O[C@H]1C2=CC=CC=C2N(C(=N)O)C2=CC=CC=C2[C@@H]1O[Si](C)(C)C | 2461.0 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TMS,isomer #3 | C[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2401.2 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TMS,isomer #4 | C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2399.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TMS,isomer #1 | C[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2476.8 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TMS,isomer #2 | C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2441.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TMS,isomer #3 | C[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2422.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TMS,isomer #1 | C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2506.6 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TMS,isomer #1 | C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2463.3 | Standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TMS,isomer #1 | C[Si](C)(C)N=C(O[Si](C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C2=CC=CC=C21 | 2906.5 | Standard polar | 33892256 | 10,11-Dihydroxycarbamazepine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1C2=CC=CC=C2N(C(=N)O)C2=CC=CC=C2[C@@H]1O | 2670.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2629.6 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2706.0 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 2770.6 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1C2=CC=CC=C2N(C(=N)O)C2=CC=CC=C2[C@@H]1O[Si](C)(C)C(C)(C)C | 2840.8 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 2807.8 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC=CC=C2[C@H](O)[C@@H](O)C2=CC=CC=C21 | 2817.7 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=N)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 2978.0 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC=CC=C2[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 2983.5 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N=C(O)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 2986.2 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 3172.1 | Semi standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 3218.8 | Standard non polar | 33892256 | 10,11-Dihydroxycarbamazepine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)N1C2=CC=CC=C2[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C2=CC=CC=C21 | 3257.7 | 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 - 10,11-Dihydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-0920000000-eb6cb3a799bd4e70259e | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 10,11-Dihydroxycarbamazepine GC-MS (3 TMS) - 70eV, Positive | splash10-00di-5139500000-4a965c4fd4ff46c9d08d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 10,11-Dihydroxycarbamazepine 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-QTOF , positive-QTOF | splash10-0udi-0090000000-582fa58dfe799f555f7d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-QTOF , positive-QTOF | splash10-01q9-0690000000-ea921c1070d79fb8606b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-QTOF , positive-QTOF | splash10-001i-0920000000-2acc6feb8a821792f63a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-QTOF , positive-QTOF | splash10-001i-0900000000-2eb3eaf74be1cde9934d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-QTOF , positive-QTOF | splash10-001i-0900000000-908137ed979bd5990aa9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-0udi-0090000000-a69751368f3b9c28fded | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-0udi-0090000000-dc082f0f810c6badb866 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-03ei-0290000000-ba77117c6385c4c74ea4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0940000000-da3e00b58237cb4d13f4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0910000000-5a8824ed936b14eb2418 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-049f0081a61bf95d3dc1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-91fcce62da1e3e5de229 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-0udi-0090000000-cf5c813c71e73c67b390 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-03ei-0290000000-6e3b8b98af2b87ded89c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0940000000-51acaa81d85d4755d122 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-1bdf38c80976bafdecd4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-8e6691f83ff3f5fba4a3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-001i-0900000000-698fb78341b98e4babb5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine LC-ESI-ITFT , positive-QTOF | splash10-0udi-0090000000-542e5ed32f92a71c0fb4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 10V, Positive-QTOF | splash10-00di-0090000000-5dc9806a3f24413a2bdf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 20V, Positive-QTOF | splash10-00b9-0090000000-2e80717b6751b35215c5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 40V, Positive-QTOF | splash10-08fu-4980000000-5b75ba83f596ac53f2fc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 10V, Negative-QTOF | splash10-00mo-5090000000-498cf604abc4e8e617b4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 20V, Negative-QTOF | splash10-004i-2090000000-fdedb62297622d12bae7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10,11-Dihydroxycarbamazepine 40V, Negative-QTOF | splash10-0006-9500000000-3a4398b915fe3442ff94 | 2016-08-03 | Wishart Lab | View Spectrum |
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