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Record Information
Version4.0
Creation Date2013-07-09 16:10:33 UTC
Update Date2017-09-27 08:43:58 UTC
HMDB IDHMDB0060977
Secondary Accession Numbers
  • HMDB60977
Metabolite Identification
Common Namedesethylamodiaquine
Descriptiondesethylamodiaquine is a metabolite of amodiaquine. Amodiaquine (trade names Camoquin, Flavoquine) is a 4-aminoquinoline compound related to chloroquine, used as an antimalarial and anti-inflammatory agent. Amodiaquine has been shown to be more effective than chloroquine in treating CRPF (chloroquine-resistant Plasmodium falciparum) malaria infections and may afford more protection than chloroquine when used as weekly prophylaxis. Amodiaquine, like chloroquine, is generally well tolerated. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
N-Monodesethylamodiaquine (deaq)ChEMBL
N-DesethylamodiaquineMeSH
4-((7-chloro-4-Quinolinyl)amino)-2-((ethylamino)methyl)phenolMeSH
MonodesethylamodiaquineMeSH
Chemical FormulaC18H18ClN3O
Average Molecular Weight327.808
Monoisotopic Molecular Weight327.11383992
IUPAC Name4-[(7-chloroquinolin-4-yl)amino]-2-[(ethylamino)methyl]phenol
Traditional Name4-[(7-chloroquinolin-4-yl)amino]-2-[(ethylamino)methyl]phenol
CAS Registry NumberNot Available
SMILES
CCNCC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
InChI Identifier
InChI=1S/C18H18ClN3O/c1-2-20-11-12-9-14(4-6-18(12)23)22-16-7-8-21-17-10-13(19)3-5-15(16)17/h3-10,20,23H,2,11H2,1H3,(H,21,22)
InChI KeyVRXFDHAGFYWGHT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • 4-aminoquinoline
  • Haloquinoline
  • Chloroquinoline
  • Aminophenol
  • P-aminophenol
  • Benzylamine
  • Phenylmethylamine
  • Aniline or substituted anilines
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aminopyridine
  • Phenol
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.0078 g/LALOGPS
logP3.96ALOGPS
logP2.87ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)10.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area57.18 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.25 m³·mol⁻¹ChemAxon
Polarizability35.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0059000000-27604621c5709d4d3e21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1693000000-ae5cf02e8ced7d6ad521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2390000000-f58bf95b94bd6a2a8a8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1019000000-22f0a74cc80e9923f42bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4198000000-85958343d63f26ffaca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9130000000-8f531754bf217e8de95cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00290
      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
      METLIN IDNot Available
      PubChem Compound122068
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available