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Record Information
Version3.6
Creation Date2013-07-09 16:10:33 UTC
Update Date2016-02-11 08:16:27 UTC
HMDB IDHMDB60977
Secondary Accession NumbersNone
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
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=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=CC=C1O
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 KeyInChIKey=VRXFDHAGFYWGHT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct ParentAminoquinolines and derivatives
Alternative Parents
Substituents
  • Chloroquinoline
  • Aminoquinoline
  • Substituted aniline
  • Phenylmethylamine
  • Benzylamine
  • Aminophenol
  • Aralkylamine
  • Phenol
  • Aniline
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • 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
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.25 m3·mol-1ChemAxon
Polarizability35.22 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 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
NuGOwiki LinkHMDB60977
Metagene LinkHMDB60977
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