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Record Information
Version3.6
Creation Date2013-07-22 19:52:09 UTC
Update Date2017-03-02 22:05:48 UTC
HMDB IDHMDB61167
Secondary Accession NumbersNone
Metabolite Identification
Common NameN,O-Didesmethylvenlafaxine glucuronide
DescriptionN,O-Didesmethylvenlafaxine glucuronide is a metabolite of venlafaxine. Venlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. First introduced by Wyeth in 1993, now marketed by Pfizer, it is licensed for the treatment of major depressive disorder (MDD), as a treatment for generalized anxiety disorder, and comorbid indications in certain anxiety disorders with depression. In 2007, venlafaxine was the sixth most commonly prescribed antidepressant on the U.S. retail market, with 17.2 million prescriptions. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H31NO8
Average Molecular Weight425.4727
Monoisotopic Molecular Weight425.204966973
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CNCC(C1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1(O)CCCCC1
InChI Identifier
InChI=1S/C21H31NO8/c1-22-11-14(21(28)9-3-2-4-10-21)12-5-7-13(8-6-12)29-20-17(25)15(23)16(24)18(30-20)19(26)27/h5-8,14-18,20,22-25,28H,2-4,9-11H2,1H3,(H,26,27)/t14?,15-,16-,17+,18-,20+/m0/s1
InChI KeyUDNAJOOLWIWCAW-SQBZNDFJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Aralkylamine
  • Cyclohexanol
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Pyran
  • Cyclic alcohol
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility2.81 mg/mLALOGPS
logP0.11ALOGPS
logP-2.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.26 m3·mol-1ChemAxon
Polarizability43.83 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 IDDBMET00958
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 LinkHMDB61167
Metagene LinkHMDB61167
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