Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:01:50 UTC
Update Date2021-09-26 22:51:06 UTC
HMDB IDHMDB0243804
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one
Description1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one, also known as energy 1 (naphyrone) or NP-pentanone, belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety. Based on a literature review a significant number of articles have been published on 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-(naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 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-Naphthalen-2-yl-2-pyrrolidin-1-ylpentan-1-oneHMDB
Energy 1 (naphyrone)HMDB
NP-PentanoneHMDB
NRG-1 (Naphyrone) CPDHMDB
NaphthylpyrovaleroneHMDB
Chemical FormulaC19H23NO
Average Molecular Weight281.399
Monoisotopic Molecular Weight281.177964365
IUPAC Name1-(naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one
Traditional Namenaphyrone
CAS Registry NumberNot Available
SMILES
CCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C19H23NO/c1-2-7-18(20-12-5-6-13-20)19(21)17-11-10-15-8-3-4-9-16(15)14-17/h3-4,8-11,14,18H,2,5-7,12-13H2,1H3
InChI KeyDTNUPBSOODGRKW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butyrophenones. Butyrophenones are compounds containing 1-phenylbutan-1-one moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassButyrophenones
Direct ParentButyrophenones
Alternative Parents
Substituents
  • Butyrophenone
  • Naphthalene
  • Aryl ketone
  • Aryl alkyl ketone
  • N-alkylpyrrolidine
  • Alpha-aminoketone
  • Pyrrolidine
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • 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
logP4.65ALOGPS
logP4.35ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.83ChemAxon
pKa (Strongest Basic)7.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.5 m³·mol⁻¹ChemAxon
Polarizability32.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+170.95830932474
DeepCCS[M-H]-168.630932474
DeepCCS[M-2H]-201.48530932474
DeepCCS[M+Na]+177.05130932474
AllCCS[M+H]+169.332859911
AllCCS[M+H-H2O]+165.732859911
AllCCS[M+NH4]+172.632859911
AllCCS[M+Na]+173.632859911
AllCCS[M-H]-177.232859911
AllCCS[M+Na-2H]-177.232859911
AllCCS[M+HCOO]-177.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-oneCCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C13258.3Standard polar33892256
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-oneCCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C12328.3Standard non polar33892256
1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-oneCCCC(N1CCCC1)C(=O)C1=CC2=CC=CC=C2C=C12283.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6920000000-e6c03fd92d9df2c9124b2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 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 - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 10V, Positive-QTOFsplash10-001i-0090000000-1a9921b0b28c94184cc42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 20V, Positive-QTOFsplash10-001i-2590000000-f93dad0477149e8ebf252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 40V, Positive-QTOFsplash10-0059-4900000000-a389df69b84c8b775fea2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 10V, Negative-QTOFsplash10-001i-0090000000-a2d4cba31dc9278eeca12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 20V, Negative-QTOFsplash10-01q9-0390000000-945ba73f9876a59008512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(Naphthalen-2-yl)-2-(pyrrolidin-1-yl)pentan-1-one 40V, Negative-QTOFsplash10-05s0-6970000000-bc7c47fe76b5dfb5cf2d2021-10-12Wishart 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 ID9418039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11243002
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 ]