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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 19:58:33 UTC
Update Date2022-11-23 22:29:19 UTC
HMDB IDHMDB0258423
Secondary Accession NumbersNone
Metabolite Identification
Common NameSpiperone
Descriptionspiperone, also known as spiropitan, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review a significant number of articles have been published on spiperone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Spiperone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Spiperone 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-[2-[4-[5-Chloro-1-(4-fluorophenyl)-indol-3-yl]-1-piperidyl]ethyl]imidazolidin-2-oneChEBI
8-(3-(p-Fluorobenzoyl)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-oneChEBI
8-(3-p-Fluorobenzoyl-1-propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decaneChEBI
EspiperonaChEBI
SpiperonumChEBI
SpiropitanChEBI
SpiroperidolMeSH
SpiroperoneMeSH
Chemical FormulaC23H26FN3O2
Average Molecular Weight395.478
Monoisotopic Molecular Weight395.200905252
IUPAC Name8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Traditional Namespiperone
CAS Registry NumberNot Available
SMILES
FC1=CC=C(C=C1)C(=O)CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)
InChI KeyDKGZKTPJOSAWFA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Phenylbutylamine
  • Azaspirodecane
  • Benzoyl
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aryl alkyl ketone
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Gamma-aminoketone
  • Piperidine
  • Benzenoid
  • Cyclic carboximidic acid
  • 3-imidazoline
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organohalogen compound
  • Amine
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.86ALOGPS
logP3.07ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.83ChemAxon
pKa (Strongest Basic)8.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111.19 m³·mol⁻¹ChemAxon
Polarizability41.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.32630932474
DeepCCS[M-H]-185.96830932474
DeepCCS[M-2H]-220.03530932474
DeepCCS[M+Na]+195.26330932474
AllCCS[M+H]+195.032859911
AllCCS[M+H-H2O]+192.532859911
AllCCS[M+NH4]+197.332859911
AllCCS[M+Na]+197.932859911
AllCCS[M-H]-194.032859911
AllCCS[M+Na-2H]-194.332859911
AllCCS[M+HCOO]-194.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
spiperoneFC1=CC=C(C=C1)C(=O)CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C14285.1Standard polar33892256
spiperoneFC1=CC=C(C=C1)C(=O)CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C13366.8Standard non polar33892256
spiperoneFC1=CC=C(C=C1)C(=O)CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C13493.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
spiperone,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O3206.6Semi standard non polar33892256
spiperone,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O3221.0Standard non polar33892256
spiperone,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O4036.0Standard polar33892256
spiperone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O3381.5Semi standard non polar33892256
spiperone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O3433.8Standard non polar33892256
spiperone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(=O)C3=CC=C(F)C=C3)CC2)C1=O4149.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Spiperone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-6950000000-9b69ba20c8b27b76a1db2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spiperone 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 - Spiperone 10V, Positive-QTOFsplash10-0002-0009000000-30a7c37074c08c8a69212016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spiperone 20V, Positive-QTOFsplash10-00n1-1359000000-dac30460c896071ac0b22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spiperone 40V, Positive-QTOFsplash10-014m-5941000000-83e1f52ccb50a8c44ce32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spiperone 10V, Negative-QTOFsplash10-0006-0009000000-3374e053ed4af2f9a2772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spiperone 20V, Negative-QTOFsplash10-0006-1109000000-6809977ff5c6ae8efb8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spiperone 40V, Negative-QTOFsplash10-0006-9721000000-b92b45860699b2709f0d2016-08-03Wishart 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 ID5075
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSpiperone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9233
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 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1