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Record Information
Version3.6
Creation Date2013-06-15 16:56:51 UTC
Update Date2016-02-11 08:08:27 UTC
HMDB IDHMDB60568
Secondary Accession Numbers
  • HMDB60674
Metabolite Identification
Common Name10,11-Dihydroxycarbamazepine
Description10,11-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)
Structure
Thumb
Synonyms
ValueSource
(-)-(S,S)-trans-10,11-dihydro-10,11-Dihydroxy-5H-dibenzo[b,F]azepine-5-carboxamideChEBI
Carbamazepine diolHMDB
Chemical FormulaC15H14N2O3
Average Molecular Weight270.2833
Monoisotopic Molecular Weight270.100442324
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
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
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)C2=CC=CC=C2N(C(O)=N)C2=CC=CC=C12
InChI Identifier
InChI=1/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-/s2
InChI KeyInChIKey=PRGQOPPDPVELEG-ZCWZLOQUNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzazepines. These 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
  • Tertiary amine
  • Secondary alcohol
  • Isourea
  • 1,2-diol
  • Azacycle
  • Carboximidic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 mg/mLALOGPS
logP0.64ALOGPS
logP1.79ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.24ChemAxon
pKa (Strongest Basic)3.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area87.78 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.73 m3·mol-1ChemAxon
Polarizability27.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00806
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07495
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60568
Metagene LinkHMDB60568
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available