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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:38:45 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240230
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxomemazine
DescriptionOxomemazine, also known as doxergan, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. In humans, oxomemazine is involved in the oxomemazine h1-antihistamine action pathway. Oxomemazine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Oxomemazine.
Structure
Data?1563892733
Synonyms
ValueSource
DoxerganKegg
(±)-OxomemazineHMDB
6487 RPHMDB
6847 RPHMDB
DysedonHMDB
EXE-TOPHMDB
ImakolHMDB
OplexHMDB
OxomemazinHMDB
OxomemazineHMDB
RP 6847HMDB
Trimeprazine 5,5-dioxideHMDB
Chemical FormulaC18H22N2O2S
Average Molecular Weight330.45
Monoisotopic Molecular Weight330.14019913
IUPAC Name10-[3-(dimethylamino)-2-methylpropyl]-10H-5lambda6-phenothiazine-5,5-dione
Traditional Name10-[3-(dimethylamino)-2-methylpropyl]-5lambda6-phenothiazine-5,5-dione
CAS Registry Number3689-50-7
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C18H22N2O2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)23(21,22)18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
InChI KeyQTQPVLDZQVPLGV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Benzenoid
  • Sulfone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process

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
logP2.81ALOGPS
logP3.18ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)8.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.22 m³·mol⁻¹ChemAxon
Polarizability35.83 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
AllCCS[M-H]-178.3131661259
AllCCS[M+H]+176.81531661259
DeepCCS[M-2H]-202.80230932474
DeepCCS[M+Na]+178.36830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxomemazineCC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C123506.9Standard polar33892256
OxomemazineCC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C122714.3Standard non polar33892256
OxomemazineCC(CN(C)C)CN1C2=CC=CC=C2S(=O)(=O)C2=CC=CC=C122637.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxomemazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k96-9772000000-3ec457a1ac6a72f2456b2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxomemazine 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 - Oxomemazine 10V, Positive-QTOFsplash10-001i-0459000000-beac9a4964166a7b9a672017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 20V, Positive-QTOFsplash10-0udr-3973000000-d263cf358db6507e3b4f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 40V, Positive-QTOFsplash10-0k9x-9220000000-905b8f542c758a6056612017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 10V, Negative-QTOFsplash10-004i-0019000000-40be074c15af8822f3462017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 20V, Negative-QTOFsplash10-0059-1269000000-497f88f76a491cc6d0402017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 40V, Negative-QTOFsplash10-001i-2690000000-0545b89cba0d13f5f7292017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 10V, Positive-QTOFsplash10-001i-0109000000-f07521e6389c4d2326142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 20V, Positive-QTOFsplash10-0a4i-9211000000-43a5cb64b6f6fba134fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 40V, Positive-QTOFsplash10-0a4i-9150000000-55461c2d42b663736dc42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 10V, Negative-QTOFsplash10-004i-0019000000-d1b5ba07ce4545141d5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 20V, Negative-QTOFsplash10-004i-0029000000-836e06008a3219269fdd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxomemazine 40V, Negative-QTOFsplash10-0006-0091000000-f633d7f3ee56a96d01f92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13820
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18281
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxomemazine
METLIN IDNot Available
PubChem CompoundNot Available
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 References
  1. Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]