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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:47:55 UTC
Update Date2021-09-14 14:57:44 UTC
HMDB IDHMDB0060658
Secondary Accession Numbers
  • HMDB0060978
  • HMDB60658
  • HMDB60978
Metabolite Identification
Common NameCarbamazepine-10,11-epoxide
DescriptionCarbamazepine-10,11-epoxide, also known as 10,11-epoxycarbamazepine, 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. Carbamazepine-10,11-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, carbamazepine-10,11-epoxide participates in a number of enzymatic reactions. In particular, carbamazepine-10,11-epoxide can be biosynthesized from carbamazepine; which is catalyzed by the enzymes cytochrome P450 2C8, cytochrome P450 3A4, cytochrome P450 3A5, cytochrome P450 3A7, and cytochrome P450 2C19. In addition, carbamazepine-10,11-epoxide can be converted into 10,11-dihydroxycarbamazepine; which is catalyzed by the enzyme epoxide hydrolase 1. An epoxide and metabolite of carbamazepine. In humans, carbamazepine-10,11-epoxide is involved in carbamazepine metabolism pathway.
Structure
Data?1563866088
Synonyms
ValueSource
10,11-EpoxycarbamazepineChEBI
Carbamazepine 10,11-oxideChEBI
Carbamazepine epoxideChEBI
Carbamazepine 10,11-epoxideHMDB
Carbamazepine epoxide, 1a-(13)C-labeledHMDB
Chemical FormulaC15H12N2O2
Average Molecular Weight252.268
Monoisotopic Molecular Weight252.089877638
IUPAC Name3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
Traditional Name3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
CAS Registry Number36507-30-9
SMILES
NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12
InChI Identifier
InChI=1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)
InChI KeyZRWWEEVEIOGMMT-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • Carbonic acid derivative
  • Urea
  • Dialkyl ether
  • Oxirane
  • Ether
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP1.58ALOGPS
logP1.97ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.86 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.98 m³·mol⁻¹ChemAxon
Polarizability25.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.331661259
DarkChem[M-H]-154.36231661259
DeepCCS[M-2H]-179.77830932474
DeepCCS[M+Na]+154.8530932474
AllCCS[M+H]+158.032859911
AllCCS[M+H-H2O]+154.032859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.832859911
AllCCS[M-H]-161.832859911
AllCCS[M+Na-2H]-160.932859911
AllCCS[M+HCOO]-160.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carbamazepine-10,11-epoxideNC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C123671.6Standard polar33892256
Carbamazepine-10,11-epoxideNC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C122161.4Standard non polar33892256
Carbamazepine-10,11-epoxideNC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C122408.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carbamazepine-10,11-epoxide,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C212302.7Semi standard non polar33892256
Carbamazepine-10,11-epoxide,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C212356.1Standard non polar33892256
Carbamazepine-10,11-epoxide,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C213328.4Standard polar33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C2412.4Semi standard non polar33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C2578.5Standard non polar33892256
Carbamazepine-10,11-epoxide,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C3166.3Standard polar33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C212512.5Semi standard non polar33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C212568.9Standard non polar33892256
Carbamazepine-10,11-epoxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C213394.2Standard polar33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2832.1Semi standard non polar33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2909.9Standard non polar33892256
Carbamazepine-10,11-epoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3233.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carbamazepine-10,11-epoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2090000000-1c00887035045a46e64c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carbamazepine-10,11-epoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOFsplash10-0ik9-0090000000-ecf7de18b8b6dca8e5742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOFsplash10-01q9-0960000000-baaab3735118a6815d952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-5f960cbf9a2cc61672702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-7ae96bba0545f7a49d652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-f5d9e3256a5025c053f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-01p9-0090000000-b4a8017bc5a22029286a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-92d916d85c6bfb1c8c8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-03ei-0390000000-8b6d0377758bc766aeca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-01q9-0950000000-54f4932e8819ef33fc592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0910000000-f98fd081a308fa16c7682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-8b69c7ac8b048b7d38922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-c63c11ed10e957dca1302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-0udi-0090000000-623298bbf57b289b12822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-03ei-0390000000-b77b3aa6c369fd8b08182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0950000000-32d3a419a11e5ffcd1322017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0910000000-72c13fa6ddd8b27641e12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-d4ce4b02188dd4b588332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-c2ed076d4e592ce2f6532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbamazepine-10,11-epoxide LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-b5886f3f5846ab71f72d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 10V, Positive-QTOFsplash10-0udi-0090000000-af9f413b6f446d69709f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 20V, Positive-QTOFsplash10-0ik9-0090000000-10bc18215ee3ab2ba1eb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 40V, Positive-QTOFsplash10-01p6-8690000000-a0c1e51c6cec85694c4a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 10V, Negative-QTOFsplash10-0k96-5090000000-ecc2f07a1eefb2949d892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 20V, Negative-QTOFsplash10-0a4i-3090000000-19d6ac25e86c1e0a6a842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbamazepine-10,11-epoxide 40V, Negative-QTOFsplash10-0006-9320000000-a52f23fc0b4f15a7d3892016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07496
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2555
PDB IDNot Available
ChEBI ID3388
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wei CY, Chung WH, Huang HW, Chen YT, Hung SI: Direct interaction between HLA-B and carbamazepine activates T cells in patients with Stevens-Johnson syndrome. J Allergy Clin Immunol. 2012 Jun;129(6):1562-9.e5. doi: 10.1016/j.jaci.2011.12.990. Epub 2012 Feb 8. [PubMed:22322005 ]
  2. McKauge L, Tyrer JH, Eadie MJ: Factors influencing simultaneous concentrations of carbamazepine and its epoxide in plasma. Ther Drug Monit. 1981;3(1):63-70. [PubMed:7233491 ]