Human Metabolome Database Version 3.5

Showing metabocard for Oxamniquine (HMDB15228)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:15 -0700
HMDB ID HMDB15228
Secondary Accession Numbers None
Metabolite Identification
Common Name Oxamniquine
Description An 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C14H21N3O3
Average Molecular Weight 279.3348
Monoisotopic Molecular Weight 279.158291553
IUPAC Name (7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
Traditional IUPAC Name oxamniquine
CAS Registry Number 21738-42-1
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 Key XCGYUJZMCCFSRP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class Hydroquinolines
Other Descriptors
  • Nitrobenzenes
Substituents
  • Nitro Compound
  • Organic Oxoazanium
  • Primary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Hydroquinolines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Schistosomicides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 147 - 149 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.24e-01 g/L Not Available
LogP 1.5 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.12 g/L ALOGPS
LogP 1.54 ALOGPS
LogP 1.57 ChemAxon
LogS -3.35 ALOGPS
pKa (strongest acidic) 14.55 ChemAxon
pKa (strongest basic) 9.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 90.11 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 79.87 ChemAxon
Polarizability 30.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01096
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01096
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01096 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4451 Link_out
KEGG Compound ID C07341 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Oxamniquine Link_out
NuGOwiki Link HMDB15228 Link_out
Metagene Link HMDB15228 Link_out
METLIN ID Not Available
PubChem Compound 4612 Link_out
PDB ID Not Available
ChEBI ID 163445 Link_out
References
Synthesis Reference See 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 Link_out

Enzymes
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA