Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2013-06-18 17:39:47 UTC |
---|
Update Date | 2019-07-23 07:14:47 UTC |
---|
HMDB ID | HMDB0060653 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 3-Hydroxycarbamazepine |
---|
Description | 3-Hydroxycarbamazepine, also known as 3OHCBZ, 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. 3-Hydroxycarbamazepine is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 3-hydroxycarbamazepine participates in a number of enzymatic reactions. In particular, 3-hydroxycarbamazepine can be biosynthesized from carbamazepine through its interaction with the enzymes cytochrome P450 3A4, cytochrome P450 2B6, and cytochrome P450 3A7. In addition, 3-hydroxycarbamazepine can be converted into 2,3-dihydroxycarbamazepine; which is catalyzed by the enzymes cytochrome P450 2C19, cytochrome P450 3A4, and cytochrome P450 3A5. In humans, 3-hydroxycarbamazepine is involved in carbamazepine metabolism pathway. 3-Hydroxycarbamazepine is a metabolite of carbamazepine. |
---|
Structure | NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12 InChI=1S/C15H12N2O2/c16-15(19)17-13-4-2-1-3-10(13)5-6-11-7-8-12(18)9-14(11)17/h1-9,18H,(H2,16,19) |
---|
Synonyms | |
---|
Chemical Formula | C15H12N2O2 |
---|
Average Molecular Weight | 252.268 |
---|
Monoisotopic Molecular Weight | 252.089877638 |
---|
IUPAC Name | 5-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide |
---|
Traditional Name | 5-hydroxy-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene-2-carboxamide |
---|
CAS Registry Number | Not Available |
---|
SMILES | NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C12 |
---|
InChI Identifier | InChI=1S/C15H12N2O2/c16-15(19)17-13-4-2-1-3-10(13)5-6-11-7-8-12(18)9-14(11)17/h1-9,18H,(H2,16,19) |
---|
InChI Key | QQCFBZCATDIWTH-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Benzazepines |
---|
Sub Class | Dibenzazepines |
---|
Direct Parent | Dibenzazepines |
---|
Alternative Parents | |
---|
Substituents | - Dibenzazepine
- 1-hydroxy-2-unsubstituted benzenoid
- Azepine
- Benzenoid
- Isourea
- Azacycle
- Carboximidic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Imine
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
3-Hydroxycarbamazepine,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(N)=O)C2=C1 | 2524.7 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,1TMS,isomer #2 | C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21 | 2451.8 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #1 | C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21 | 2486.9 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #1 | C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21 | 2501.2 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #1 | C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C)C=C21 | 3432.2 | Standard polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C | 2542.2 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C | 2730.5 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TMS,isomer #2 | C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C | 3624.0 | Standard polar | 33892256 | 3-Hydroxycarbamazepine,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1 | 2550.8 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1 | 2762.1 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C)[Si](C)(C)C)C2=C1 | 3327.2 | Standard polar | 33892256 | 3-Hydroxycarbamazepine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(N)=O)C2=C1 | 2776.0 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21 | 2670.2 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21 | 2907.2 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21 | 2887.7 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C=CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21 | 3588.8 | Standard polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C | 2958.1 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C | 3045.6 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C=CC2=CC=C(O)C=C21)[Si](C)(C)C(C)(C)C | 3647.9 | Standard polar | 33892256 | 3-Hydroxycarbamazepine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1 | 3188.6 | Semi standard non polar | 33892256 | 3-Hydroxycarbamazepine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1 | 3289.1 | Standard non polar | 33892256 | 3-Hydroxycarbamazepine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC=C3N(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1 | 3541.1 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-1190000000-a63cd184d192b469a0bb | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine GC-MS (1 TMS) - 70eV, Positive | splash10-05gi-4091000000-aa4e3a154aab49a9f90c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Hydroxycarbamazepine 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 |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Positive-QTOF | splash10-0udr-0090000000-01f6142623d495374520 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Positive-QTOF | splash10-03dr-0090000000-83afddda616892de1708 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Positive-QTOF | splash10-0a5c-0970000000-df18c252a4ebb6e19782 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Negative-QTOF | splash10-0pbc-5090000000-b4cf89fc59b9af7e7aac | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Negative-QTOF | splash10-0a4i-2090000000-14c0e5b2cb42384e554d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Negative-QTOF | splash10-0006-9220000000-5bb7e2feabf45d211373 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Positive-QTOF | splash10-0udi-0090000000-068391fc308918509fc3 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Positive-QTOF | splash10-08fr-0090000000-08755f0ae6819797e32e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Positive-QTOF | splash10-0a4i-0790000000-41511f8d7b33a31c1ea9 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 10V, Negative-QTOF | splash10-0udi-0090000000-229652fa3e4351b39559 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 20V, Negative-QTOF | splash10-0a4i-0090000000-9f12ac38c8faae87e87f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Hydroxycarbamazepine 40V, Negative-QTOF | splash10-0a4i-0090000000-296de1c6f0c6cab3a7f1 | 2021-10-12 | Wishart Lab | View Spectrum |
|
---|