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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:10:33 UTC
Update Date2019-07-23 07:15:30 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
Data?1563866130
Synonyms
ValueSource
N-Monodesethylamodiaquine (deaq)HMDB
N-DesethylamodiaquineHMDB
4-((7-Chloro-4-quinolinyl)amino)-2-((ethylamino)methyl)phenolHMDB
MonodesethylamodiaquineHMDB
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
Description Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines 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
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+181.65530932474
DeepCCS[M-H]-179.29730932474
DeepCCS[M-2H]-212.24630932474
DeepCCS[M+Na]+187.74830932474
AllCCS[M+H]+176.532859911
AllCCS[M+H-H2O]+173.332859911
AllCCS[M+NH4]+179.432859911
AllCCS[M+Na]+180.332859911
AllCCS[M-H]-178.332859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-177.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
desethylamodiaquineCCNCC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C14361.3Standard polar33892256
desethylamodiaquineCCNCC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C13167.3Standard non polar33892256
desethylamodiaquineCCNCC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C13358.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
desethylamodiaquine,1TMS,isomer #1CCNCC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C3106.3Semi standard non polar33892256
desethylamodiaquine,1TMS,isomer #2CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O)[Si](C)(C)C3198.6Semi standard non polar33892256
desethylamodiaquine,1TMS,isomer #3CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O2984.8Semi standard non polar33892256
desethylamodiaquine,2TMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3182.4Semi standard non polar33892256
desethylamodiaquine,2TMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3065.3Standard non polar33892256
desethylamodiaquine,2TMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3706.9Standard polar33892256
desethylamodiaquine,2TMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2946.4Semi standard non polar33892256
desethylamodiaquine,2TMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2917.5Standard non polar33892256
desethylamodiaquine,2TMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C3439.8Standard polar33892256
desethylamodiaquine,2TMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O)[Si](C)(C)C3042.5Semi standard non polar33892256
desethylamodiaquine,2TMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O)[Si](C)(C)C3100.1Standard non polar33892256
desethylamodiaquine,2TMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O)[Si](C)(C)C3659.8Standard polar33892256
desethylamodiaquine,3TMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3051.8Semi standard non polar33892256
desethylamodiaquine,3TMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3007.2Standard non polar33892256
desethylamodiaquine,3TMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C)[Si](C)(C)C3353.2Standard polar33892256
desethylamodiaquine,1TBDMS,isomer #1CCNCC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C3334.8Semi standard non polar33892256
desethylamodiaquine,1TBDMS,isomer #2CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O)[Si](C)(C)C(C)(C)C3421.3Semi standard non polar33892256
desethylamodiaquine,1TBDMS,isomer #3CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O3209.2Semi standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3592.9Semi standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3481.8Standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #1CCN(CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3823.9Standard polar33892256
desethylamodiaquine,2TBDMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3391.3Semi standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3359.5Standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #2CCNCC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3581.1Standard polar33892256
desethylamodiaquine,2TBDMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O)[Si](C)(C)C(C)(C)C3492.3Semi standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O)[Si](C)(C)C(C)(C)C3477.0Standard non polar33892256
desethylamodiaquine,2TBDMS,isomer #3CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O)[Si](C)(C)C(C)(C)C3743.2Standard polar33892256
desethylamodiaquine,3TBDMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3664.9Semi standard non polar33892256
desethylamodiaquine,3TBDMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3541.0Standard non polar33892256
desethylamodiaquine,3TBDMS,isomer #1CCN(CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3569.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - desethylamodiaquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gm-6195000000-dfaa5f4f4fc5bca843e22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - desethylamodiaquine GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-5009000000-3470c1552681d496cfd12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - desethylamodiaquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - desethylamodiaquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 10V, Positive-QTOFsplash10-0059-0059000000-27604621c5709d4d3e212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 20V, Positive-QTOFsplash10-053r-1693000000-ae5cf02e8ced7d6ad5212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 40V, Positive-QTOFsplash10-0a4i-2390000000-f58bf95b94bd6a2a8a8b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 10V, Negative-QTOFsplash10-004i-1019000000-22f0a74cc80e9923f42b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 20V, Negative-QTOFsplash10-004i-4198000000-85958343d63f26ffaca82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 40V, Negative-QTOFsplash10-0006-9130000000-8f531754bf217e8de95c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 10V, Positive-QTOFsplash10-001i-0094000000-25fed80f40762c48a4dd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 20V, Positive-QTOFsplash10-001i-0091000000-e35c616c6b5010aa670b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 40V, Positive-QTOFsplash10-053r-0190000000-4e344e845969d3147cf82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 10V, Negative-QTOFsplash10-004i-0019000000-459c0d65ec8dd257c0e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 20V, Negative-QTOFsplash10-001i-1093000000-618e1c789c589aa900f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desethylamodiaquine 40V, Negative-QTOFsplash10-00lr-2290000000-6b882a1532d8ac40a7192021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available