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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 17:08:23 UTC
Update Date2021-09-26 23:12:25 UTC
HMDB IDHMDB0256615
Secondary Accession NumbersNone
Metabolite Identification
Common NamePirsidomine
DescriptionN-[3-(2,6-dimethylpiperidin-1-yl)-5H-1,2,3λ⁵-oxadiazol-5-ylidene]-4-methoxybenzamide belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Based on a literature review very few articles have been published on N-[3-(2,6-dimethylpiperidin-1-yl)-5H-1,2,3λ⁵-oxadiazol-5-ylidene]-4-methoxybenzamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pirsidomine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pirsidomine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H22N4O3
Average Molecular Weight330.388
Monoisotopic Molecular Weight330.169190584
IUPAC Name3-(2,6-dimethylpiperidin-1-yl)-5-{[(4-methoxyphenyl)(oxido)methylidene]amino}-1,2,3lambda5-oxadiazol-3-ylium
Traditional Name3-(2,6-dimethylpiperidin-1-yl)-5-{[(4-methoxyphenyl)(oxido)methylidene]amino}-1,2,3lambda5-oxadiazol-3-ylium
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1)C([O-])=NC1=C[N+](=NO1)N1C(C)CCCC1C
InChI Identifier
InChI=1S/C17H22N4O3/c1-12-5-4-6-13(2)21(12)20-11-16(24-19-20)18-17(22)14-7-9-15(23-3)10-8-14/h7-13H,4-6H2,1-3H3
InChI KeyTXPUBJSOHAMNEI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Piperidine
  • Azole
  • Heteroaromatic compound
  • Oxadiazole
  • 1,2,3-oxadiazole
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic oxygen compound
  • Organic salt
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
logP1.08ALOGPS
logP2.33ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area77.8 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity123.54 m³·mol⁻¹ChemAxon
Polarizability36.06 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]+164.28530932474
DeepCCS[M-H]-161.76730932474
DeepCCS[M-2H]-196.28730932474
DeepCCS[M+Na]+171.40930932474
AllCCS[M+H]+182.032859911
AllCCS[M+H-H2O]+178.932859911
AllCCS[M+NH4]+184.932859911
AllCCS[M+Na]+185.732859911
AllCCS[M-H]-181.332859911
AllCCS[M+Na-2H]-181.432859911
AllCCS[M+HCOO]-181.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PirsidomineCOC1=CC=C(C=C1)C([O-])=NC1=C[N+](=NO1)N1C(C)CCCC1C3185.7Standard polar33892256
PirsidomineCOC1=CC=C(C=C1)C([O-])=NC1=C[N+](=NO1)N1C(C)CCCC1C2738.7Standard non polar33892256
PirsidomineCOC1=CC=C(C=C1)C([O-])=NC1=C[N+](=NO1)N1C(C)CCCC1C2875.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pirsidomine GC-MS (Non-derivatized) - 70eV, Positivesplash10-02a9-3913000000-d9ec7c5d172976287dad2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pirsidomine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 ID8081218
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23376546
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]