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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:46:29 UTC
HMDB IDHMDB0015228
Secondary Accession Numbers
  • HMDB15228
Metabolite Identification
Common NameOxamniquine
DescriptionOxamniquine, also known as mansil, belongs to the class of organic compounds known as nitroquinolines and derivatives. Nitroquinolines and derivatives are compounds containing a nitro group attached to a quinoline moiety. Oxamniquine is a drug which is used for treatment of schistosomiasis caused by schistosoma mansoni. Based on a literature review a significant number of articles have been published on Oxamniquine.
Structure
Data?1582753272
Synonyms
ValueSource
MansilKegg
VansilKegg
OxaminiquineHMDB
OxamniquineMeSH
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
Description Belongs to the class of organic compounds known as nitroquinolines and derivatives. Nitroquinolines and derivatives are compounds containing a nitro group attached to a quinoline moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNitroquinolines 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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 - 149 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(1.54) g/LALOGPS
logP10(1.57) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
Refractivity79.86 m³·mol⁻¹ChemAxon
Polarizability30.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.12931661259
DarkChem[M-H]-165.02831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxamniquineCC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O3615.0Standard polar33892256
OxamniquineCC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O2402.0Standard non polar33892256
OxamniquineCC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O2600.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxamniquine,1TMS,isomer #1CC(C)NCC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N12499.2Semi standard non polar33892256
Oxamniquine,1TMS,isomer #2CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C2588.8Semi standard non polar33892256
Oxamniquine,1TMS,isomer #3CC(C)NCC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C2411.2Semi standard non polar33892256
Oxamniquine,2TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C2563.7Semi standard non polar33892256
Oxamniquine,2TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C2679.2Standard non polar33892256
Oxamniquine,2TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C3149.3Standard polar33892256
Oxamniquine,2TMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C2421.5Semi standard non polar33892256
Oxamniquine,2TMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C2596.0Standard non polar33892256
Oxamniquine,2TMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C2873.6Standard polar33892256
Oxamniquine,2TMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2467.2Semi standard non polar33892256
Oxamniquine,2TMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2734.7Standard non polar33892256
Oxamniquine,2TMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2967.0Standard polar33892256
Oxamniquine,3TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2533.2Semi standard non polar33892256
Oxamniquine,3TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2789.4Standard non polar33892256
Oxamniquine,3TMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C)[Si](C)(C)C2782.8Standard polar33892256
Oxamniquine,1TBDMS,isomer #1CC(C)NCC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N12708.3Semi standard non polar33892256
Oxamniquine,1TBDMS,isomer #2CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C(C)(C)C2849.2Semi standard non polar33892256
Oxamniquine,1TBDMS,isomer #3CC(C)NCC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C2676.4Semi standard non polar33892256
Oxamniquine,2TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C(C)(C)C3027.6Semi standard non polar33892256
Oxamniquine,2TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C(C)(C)C3160.2Standard non polar33892256
Oxamniquine,2TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1)[Si](C)(C)C(C)(C)C3274.0Standard polar33892256
Oxamniquine,2TBDMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C2916.2Semi standard non polar33892256
Oxamniquine,2TBDMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C3083.2Standard non polar33892256
Oxamniquine,2TBDMS,isomer #2CC(C)NCC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C3062.2Standard polar33892256
Oxamniquine,2TBDMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2996.9Semi standard non polar33892256
Oxamniquine,2TBDMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3216.2Standard non polar33892256
Oxamniquine,2TBDMS,isomer #3CC(C)N(CC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3134.1Standard polar33892256
Oxamniquine,3TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3266.1Semi standard non polar33892256
Oxamniquine,3TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3470.1Standard non polar33892256
Oxamniquine,3TBDMS,isomer #1CC(C)N(CC1CCC2=CC(CO[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3030.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4290000000-26820b2602dda372b4222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (1 TMS) - 70eV, Positivesplash10-00el-7059000000-0486df00275bb05babfb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxamniquine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine LC-ESI-QTOF , positive-QTOFsplash10-001i-0090000000-cbc05dcd3c76cb5e6dbc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine LC-ESI-QTOF , positive-QTOFsplash10-00di-0090000000-13f1262c88faee1964442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine LC-ESI-QTOF , positive-QTOFsplash10-00di-0950000000-082ec38664b574d25a9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine LC-ESI-QTOF , positive-QTOFsplash10-00dj-0900000000-781fed8c05ecf56fc5b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine LC-ESI-QTOF , positive-QTOFsplash10-006t-0900000000-9e5d872a8378b48f787f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine , positive-QTOFsplash10-00dj-2910000000-90237e532f4d41c891922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 40V, Positive-QTOFsplash10-00dj-0900000000-6f592e82c12fcbf329882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 40V, Positive-QTOFsplash10-00dj-0900000000-781fed8c05ecf56fc5b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 50V, Positive-QTOFsplash10-006t-0900000000-c6fbb1af7c6e2bdcc2b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 50V, Positive-QTOFsplash10-006t-0900000000-12ee7e983c1bc1a0c6c12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 40V, Positive-QTOFsplash10-00dj-0900000000-59cf50ada2529814df502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 50V, Positive-QTOFsplash10-006t-0900000000-9e5d872a8378b48f787f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 30V, Positive-QTOFsplash10-00di-0950000000-082ec38664b574d25a9c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 10V, Positive-QTOFsplash10-001i-0090000000-cbc05dcd3c76cb5e6dbc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxamniquine 20V, Positive-QTOFsplash10-00di-0090000000-13f1262c88faee1964442021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 10V, Positive-QTOFsplash10-001i-0090000000-4660df5011f198fa6c742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 20V, Positive-QTOFsplash10-0fk9-1090000000-e66ef42eef39585bc8212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 40V, Positive-QTOFsplash10-0006-9110000000-6ada4b677afb226e2f5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 10V, Negative-QTOFsplash10-004i-1090000000-6b38752e9a8cb09df25f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 20V, Negative-QTOFsplash10-056r-6090000000-dca977bec43ce6e6f4b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxamniquine 40V, Negative-QTOFsplash10-0a4i-9000000000-fd142e629b6b792054902016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01096 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01096 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01096
Phenol Explorer Compound IDNot Available
FooDB 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 ID78416
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]