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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-12-07 02:49:55 UTC
HMDB IDHMDB0015228
Secondary Accession Numbers
  • HMDB15228
Metabolite Identification
Common NameOxamniquine
DescriptionAn anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)
Structure
Thumb
Synonyms
ValueSource
MansilKegg
VansilKegg
OxaminiquineMeSH
Chemical FormulaC14H21N3O3
Average Molecular Weight279.3348
Monoisotopic Molecular Weight279.158291553
IUPAC Name(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
Traditional Nameoxamniquine
CAS Registry Number21738-42-1
SMILES
CC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O
InChI Identifier
InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3
InChI KeyXCGYUJZMCCFSRP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct ParentNitroquinolines and derivatives
Alternative Parents
Substituents
  • Nitroquinoline
  • Tetrahydroquinoline
  • Nitroaromatic compound
  • Secondary aliphatic/aromatic amine
  • Aralkylamine
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Secondary aliphatic amine
  • Organic oxoazanium
  • Secondary amine
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic alcohol
  • Organic zwitterion
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physiological effect

Health effect:

  Health condition:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.54ALOGPS
logP1.57ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.11 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.87 m³·mol⁻¹ChemAxon
Polarizability30.19 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-03di-4290000000-26820b2602dda372b422View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00el-7059000000-0486df00275bb05babfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0090000000-cbc05dcd3c76cb5e6dbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-13f1262c88faee196444View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0950000000-082ec38664b574d25a9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dj-0900000000-781fed8c05ecf56fc5b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006t-0900000000-9e5d872a8378b48f787fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-2910000000-90237e532f4d41c89192View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-4660df5011f198fa6c74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-1090000000-e66ef42eef39585bc821View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-6ada4b677afb226e2f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1090000000-6b38752e9a8cb09df25fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-6090000000-dca977bec43ce6e6f4b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-fd142e629b6b79205490View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01096 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01096 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01096
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4451
KEGG Compound IDC07341
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxamniquine
METLIN IDNot Available
PubChem Compound4612
PDB IDNot Available
ChEBI ID163445
References
Synthesis ReferenceSee General references, Filho et. al. for synthesis of oxamniquine methacylate.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. [PubMed:17134907 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]