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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-08-29 02:45:00 UTC
Update Date2021-09-26 22:48:55 UTC
HMDB IDHMDB0242283
Secondary Accession NumbersNone
Metabolite Identification
Common Name(1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone
Description(1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone, also known as JWH 019, belongs to the class of organic compounds known as naphthoylindoles. These are polycyclic compounds containing an indole moiety that is N-linked to the carboxamide group attached to naphthalene. Based on a literature review a significant number of articles have been published on (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1-hexyl-1h-indol-3-yl)(naphthalen-1-yl)methanone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 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
JWH 019HMDB
(1-Hexyl-1H-indol-3-yl)-1-naphthalenylmethanoneHMDB
JWH-019HMDB
Chemical FormulaC25H25NO
Average Molecular Weight355.481
Monoisotopic Molecular Weight355.193614429
IUPAC Name1-hexyl-3-(naphthalene-1-carbonyl)-1H-indole
Traditional Name1-hexyl-3-(naphthalene-1-carbonyl)indole
CAS Registry NumberNot Available
SMILES
CCCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C12
InChI Identifier
InChI=1S/C25H25NO/c1-2-3-4-9-17-26-18-23(21-14-7-8-16-24(21)26)25(27)22-15-10-12-19-11-5-6-13-20(19)22/h5-8,10-16,18H,2-4,9,17H2,1H3
InChI KeyPALJPGHWDUHUPO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthoylindoles. These are polycyclic compounds containing an indole moiety that is N-linked to the carboxamide group attached to naphthalene.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNaphthoylindoles
Direct ParentNaphthoylindoles
Alternative Parents
Substituents
  • Naphthoylindole
  • Benzoylindole
  • 1-naphthalenecarboxylic acid or derivatives
  • Indolecarboxylic acid derivative
  • N-alkylindole
  • Naphthalene
  • Indole
  • Aryl ketone
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen 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
logP6.51ALOGPS
logP6.96ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.14 m³·mol⁻¹ChemAxon
Polarizability42.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-226.62730932474
DeepCCS[M+Na]+202.86130932474
AllCCS[M+H]+190.432859911
AllCCS[M+H-H2O]+187.532859911
AllCCS[M+NH4]+193.132859911
AllCCS[M+Na]+193.832859911
AllCCS[M-H]-194.232859911
AllCCS[M+Na-2H]-194.132859911
AllCCS[M+HCOO]-194.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanoneCCCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C124374.8Standard polar33892256
(1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanoneCCCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C123079.7Standard non polar33892256
(1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanoneCCCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C123358.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9444000000-6089858ffe5fd39e3e052021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 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-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 10V, Positive-QTOFsplash10-0a4i-0009000000-b3a79e086432130253302019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 20V, Positive-QTOFsplash10-0a4r-5954000000-812b45e8e7be27bf474a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 40V, Positive-QTOFsplash10-0a4l-7900000000-2608bc6df5558086020b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 10V, Negative-QTOFsplash10-0udi-0009000000-d907d5b26100cc4a97772019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 20V, Negative-QTOFsplash10-0udi-0279000000-f613156652fee5c0e4702019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 40V, Negative-QTOFsplash10-00tf-1930000000-4c2199308bdd6d6c7a642019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 10V, Positive-QTOFsplash10-0a4i-0009000000-fda263e0a20d6626b8ec2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 20V, Positive-QTOFsplash10-0a4i-0916000000-eb665d738553421c36052021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 40V, Positive-QTOFsplash10-056r-0900000000-c04dc1bcda8fc38d48b72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 10V, Negative-QTOFsplash10-0udi-0009000000-c66abc8173f8c7b346b22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 20V, Negative-QTOFsplash10-0fk9-0098000000-4ddc0a03e3c4f9d4650f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone 40V, Negative-QTOFsplash10-00xu-0791000000-e1fdc240d7012a73d48a2021-10-12Wishart 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 ID24598813
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52224389
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 ]