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Record Information
Version3.6
Creation Date2013-07-22 19:50:57 UTC
Update Date2017-03-02 22:05:47 UTC
HMDB IDHMDB61147
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydroxyclomipramine glucuronide
DescriptionHydroxyclomipramine glucuronide is a metabolite of clomipramine. Clomipramine (trademarked as Anafranil) is a tricyclic antidepressant (TCA). It was developed in the 1960s by the Swiss drug manufacturer Geigy (now known as Novartis) and has been in clinical use worldwide ever since. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H31ClN2O7
Average Molecular Weight506.976
Monoisotopic Molecular Weight506.181979063
IUPAC Name(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=C(CCC3=C1C=CC=C3O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=CC(Cl)=C2
InChI Identifier
InChI=1S/C25H31ClN2O7/c1-27(2)11-4-12-28-17-5-3-6-19(16(17)10-8-14-7-9-15(26)13-18(14)28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h3,5-7,9,13,20-23,25,29-31H,4,8,10-12H2,1-2H3,(H,32,33)/t20-,21-,22+,23-,25+/m0/s1
InChI KeyKLJBBCVPINUDOY-LYVDORBWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Phenolic glycoside
  • Dibenzazepine
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Alkyldiarylamine
  • O-glycosyl compound
  • Glycosyl compound
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Beta-hydroxy acid
  • Aryl chloride
  • Aryl halide
  • Monosaccharide
  • Hydroxy acid
  • Oxane
  • Pyran
  • Benzenoid
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organochloride
  • Organohalogen compound
  • 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 Solubility0.79 mg/mLALOGPS
logP2.58ALOGPS
logP-0.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.93 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.4 m3·mol-1ChemAxon
Polarizability51.64 Å3ChemAxon
Number of Rings4ChemAxon
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 IDDBMET00871
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61147
Metagene LinkHMDB61147
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