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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 22:49:18 UTC
Update Date2021-09-26 23:17:42 UTC
HMDB IDHMDB0259872
Secondary Accession NumbersNone
Metabolite Identification
Common NameVonoprazan
DescriptionVonoprazan belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. Based on a literature review a significant number of articles have been published on Vonoprazan. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vonoprazan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vonoprazan 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
Synonyms
ValueSource
1-(5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamineMeSH
TAK 438MeSH
TAK-438MeSH
Chemical FormulaC17H16FN3O2S
Average Molecular Weight345.39
Monoisotopic Molecular Weight345.094726104
IUPAC Name{[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]methyl}(methyl)amine
Traditional Name{[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)pyrrol-3-yl]methyl}(methyl)amine
CAS Registry NumberNot Available
SMILES
CNCC1=CN(C(=C1)C1=CC=CC=C1F)S(=O)(=O)C1=CC=CN=C1
InChI Identifier
InChI=1S/C17H16FN3O2S/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14/h2-9,11-12,19H,10H2,1H3
InChI KeyBFDBKMOZYNOTPK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 2-phenylpyrrole
  • Pyridine-3-sulfonamide
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Secondary amine
  • Azacycle
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organic oxide
  • Amine
  • 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
logP1.78ALOGPS
logP2.03ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.16 m³·mol⁻¹ChemAxon
Polarizability34.23 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]+179.30732859911
AllCCS[M+H-H2O]+176.05132859911
AllCCS[M+Na]+183.18732859911
AllCCS[M+NH4]+182.32232859911
AllCCS[M-H]-177.832859911
AllCCS[M+Na-2H]-177.35832859911
AllCCS[M+HCOO]-177.00932859911
DeepCCS[M+H]+177.94730932474
DeepCCS[M-H]-175.35730932474
DeepCCS[M-2H]-209.88130932474
DeepCCS[M+Na]+185.94230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VonoprazanCNCC1=CN(C(=C1)C1=CC=CC=C1F)S(=O)(=O)C1=CC=CN=C14329.8Standard polar33892256
VonoprazanCNCC1=CN(C(=C1)C1=CC=CC=C1F)S(=O)(=O)C1=CC=CN=C12735.1Standard non polar33892256
VonoprazanCNCC1=CN(C(=C1)C1=CC=CC=C1F)S(=O)(=O)C1=CC=CN=C12691.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vonoprazan,1TMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C2894.8Semi standard non polar33892256
Vonoprazan,1TMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C2745.8Standard non polar33892256
Vonoprazan,1TMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C3563.7Standard polar33892256
Vonoprazan,1TBDMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C(C)(C)C3136.9Semi standard non polar33892256
Vonoprazan,1TBDMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C(C)(C)C2946.8Standard non polar33892256
Vonoprazan,1TBDMS,isomer #1CN(CC1=CN(S(=O)(=O)C2=CC=CN=C2)C(C2=CC=CC=C2F)=C1)[Si](C)(C)C(C)(C)C3646.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vonoprazan GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-4935000000-d3bc83f50b63002651a02021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vonoprazan 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 - Vonoprazan 10V, Positive-QTOFsplash10-0002-0009000000-ff2483eab682064377782017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vonoprazan 20V, Positive-QTOFsplash10-00kb-1159000000-191b06bed9116b7baead2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vonoprazan 40V, Positive-QTOFsplash10-0h9u-4920000000-53a3be224766fcec42e92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vonoprazan 10V, Negative-QTOFsplash10-0006-0009000000-ce0c31ac139a21dce87b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vonoprazan 20V, Negative-QTOFsplash10-0006-3319000000-1cbf426b59b5ff1321ca2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vonoprazan 40V, Negative-QTOFsplash10-01ox-9610000000-856eb51b480ede82fbeb2017-07-26Wishart 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 IDDB11739
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13112797
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVonoprazan
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. 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 ]