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Record Information
Version3.6
Creation Date2013-07-04 18:54:41 UTC
Update Date2017-03-02 22:05:21 UTC
HMDB IDHMDB60716
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxy-desipramine glucuronide
Description2-Hydroxy-desipramine glucuronide is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H30N2O7
Average Molecular Weight458.5042
Monoisotopic Molecular Weight458.205301324
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-yl}oxy)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=CC=CC=C2CCC2=CC(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=CC=C12
InChI Identifier
InChI=1S/C24H30N2O7/c1-25-11-4-12-26-17-6-3-2-5-14(17)7-8-15-13-16(9-10-18(15)26)32-24-21(29)19(27)20(28)22(33-24)23(30)31/h2-3,5-6,9-10,13,19-22,24-25,27-29H,4,7-8,11-12H2,1H3,(H,30,31)/t19-,20-,21+,22-,24+/m0/s1
InChI KeyXJHAOJJEVSPMBA-QMDPOKHVSA-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
  • Dibenzazepine
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Alkyldiarylamine
  • O-glycosyl compound
  • Glycosyl compound
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Beta-hydroxy acid
  • Hydroxy acid
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Pyran
  • Secondary alcohol
  • Tertiary amine
  • Amino acid
  • Amino acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Polyol
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organonitrogen 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 Solubility1.76 mg/mLALOGPS
logP0.58ALOGPS
logP-0.83ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area131.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.3 m3·mol-1ChemAxon
Polarizability48.99 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 IDDBMET00679
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 LinkHMDB60716
Metagene LinkHMDB60716
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