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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 17:49:17 UTC
Update Date2021-09-26 23:13:17 UTC
HMDB IDHMDB0257133
Secondary Accession NumbersNone
Metabolite Identification
Common NameReduced ketanserin
Description3-(2-{4-[(4-fluorophenyl)(hydroxy)methyl]piperidin-1-yl}ethyl)-2-hydroxy-3,4-dihydroquinazolin-4-one belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Based on a literature review very few articles have been published on 3-(2-{4-[(4-fluorophenyl)(hydroxy)methyl]piperidin-1-yl}ethyl)-2-hydroxy-3,4-dihydroquinazolin-4-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Reduced ketanserin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Reduced ketanserin 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
3-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4-(1H,3H)quinazolinedioneMeSH
Chemical FormulaC22H24FN3O3
Average Molecular Weight397.45
Monoisotopic Molecular Weight397.180169808
IUPAC Name3-(2-{4-[(4-fluorophenyl)(hydroxy)methyl]piperidin-1-yl}ethyl)-1,2,3,4-tetrahydroquinazoline-2,4-dione
Traditional Name3-(2-{4-[(4-fluorophenyl)(hydroxy)methyl]piperidin-1-yl}ethyl)-1H-quinazoline-2,4-dione
CAS Registry NumberNot Available
SMILES
OC(C1CCN(CCN2C(=O)NC3=CC=CC=C3C2=O)CC1)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C22H24FN3O3/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29/h1-8,16,20,27H,9-14H2,(H,24,29)
InChI KeyCSAITASUWRGAOT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Fluorobenzene
  • Halobenzene
  • Pyrimidone
  • Aralkylamine
  • Aryl halide
  • Aryl fluoride
  • Benzenoid
  • Monocyclic benzene moiety
  • Piperidine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Tertiary amine
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.45ALOGPS
logP3.34ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.42ChemAxon
pKa (Strongest Basic)7.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.88 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.73 m³·mol⁻¹ChemAxon
Polarizability41.06 ųChemAxon
Number of Rings4ChemAxon
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]+194.85630932474
DeepCCS[M-H]-192.49830932474
DeepCCS[M-2H]-226.78230932474
DeepCCS[M+Na]+202.01930932474
AllCCS[M+H]+192.632859911
AllCCS[M+H-H2O]+190.232859911
AllCCS[M+NH4]+194.832859911
AllCCS[M+Na]+195.532859911
AllCCS[M-H]-190.932859911
AllCCS[M+Na-2H]-190.932859911
AllCCS[M+HCOO]-191.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Reduced ketanserinOC(C1CCN(CCN2C(=O)NC3=CC=CC=C3C2=O)CC1)C1=CC=C(F)C=C14145.2Standard polar33892256
Reduced ketanserinOC(C1CCN(CCN2C(=O)NC3=CC=CC=C3C2=O)CC1)C1=CC=C(F)C=C13370.1Standard non polar33892256
Reduced ketanserinOC(C1CCN(CCN2C(=O)NC3=CC=CC=C3C2=O)CC1)C1=CC=C(F)C=C13636.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Reduced ketanserin,2TMS,isomer #1C[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C)C2=O)CC13298.4Semi standard non polar33892256
Reduced ketanserin,2TMS,isomer #1C[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C)C2=O)CC13172.0Standard non polar33892256
Reduced ketanserin,2TMS,isomer #1C[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C)C2=O)CC13941.7Standard polar33892256
Reduced ketanserin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=O)CC13680.2Semi standard non polar33892256
Reduced ketanserin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=O)CC13543.9Standard non polar33892256
Reduced ketanserin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C1=CC=C(F)C=C1)C1CCN(CCN2C(=O)C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=O)CC14030.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3951000000-c51277c86a18ab17359f2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Reduced ketanserin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart 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 ID137722
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound156394
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 ]