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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-02-03 11:51:29 UTC
Update Date2023-02-21 17:17:33 UTC
HMDB IDHMDB0011664
Secondary Accession Numbers
  • HMDB11664
Metabolite Identification
Common Name3-Methylene-indolenine
Description3-Methylene-indolenine is an electrophilic molecule produced by the action of cytochrome P450 2F1 on 3-methylindole (3MI). 3-Methylindole (3MI) is a naturally occurring pulmonary toxin that requires metabolic activation. In particular, 3MI-induced pneumotoxicity arises from cytochrome P-450-catalyzed dehydrogenation of 3MI to an electrophilic methylene imine (3-methyleneindolenine), which covalently binds to cellular macromolecules. Members of the CYP2F gene subfamily are selectively expressed in lung tissues and have been implicated as important catalysts in the formation of reactive intermediates from several pneumotoxic chemicals. (PMID: 10383923 ).
Structure
Data?1676999852
Synonyms
ValueSource
3-Methylene-3H-indoleHMDB
3-MethyleneindolenineHMDB
3-Methyleneindolenine, conjugate acidMeSH, HMDB
3-Methylene-indolenineMeSH
Chemical FormulaC9H7N
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
IUPAC Name3-methylidene-3H-indole
Traditional Name3-methyleneindolenine
CAS Registry Number40642-83-9
SMILES
C=C1C=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H7N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6H,1H2
InChI KeyBCNUXXXHEIUHJB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • Benzenoid
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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
Water Solubility0.24 g/LALOGPS
logP2.4ALOGPS
logP2.23ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)5.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.51 m³·mol⁻¹ChemAxon
Polarizability14.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.67331661259
DarkChem[M-H]-124.77431661259
DeepCCS[M-2H]-159.40530932474
DeepCCS[M+Na]+134.48930932474
AllCCS[M+H]+123.232859911
AllCCS[M+H-H2O]+118.232859911
AllCCS[M+NH4]+127.932859911
AllCCS[M+Na]+129.332859911
AllCCS[M-H]-123.132859911
AllCCS[M+Na-2H]-124.132859911
AllCCS[M+HCOO]-125.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylene-indolenineC=C1C=NC2=CC=CC=C122173.5Standard polar33892256
3-Methylene-indolenineC=C1C=NC2=CC=CC=C121182.2Standard non polar33892256
3-Methylene-indolenineC=C1C=NC2=CC=CC=C121255.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylene-indolenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0900000000-3d84acfd95cbc3a7b6792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylene-indolenine 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 - 3-Methylene-indolenine 10V, Positive-QTOFsplash10-001i-0900000000-dfa6172462414820c0442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Positive-QTOFsplash10-001i-0900000000-6e9ca0aeeaa7b26ee4c42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Positive-QTOFsplash10-0udi-3900000000-f2394a06312955f7f2012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Negative-QTOFsplash10-004i-0900000000-bb1e304ced3d5e0fad572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Negative-QTOFsplash10-004i-0900000000-bb1e304ced3d5e0fad572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Negative-QTOFsplash10-004i-2900000000-3ea963fdae7c035975122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Positive-QTOFsplash10-001i-0900000000-0040a9215518cbf578982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Positive-QTOFsplash10-001i-0900000000-39afe1a13df2499e1f7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Positive-QTOFsplash10-0fb9-5900000000-361d14169ac7b58a59bf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Negative-QTOFsplash10-004i-0900000000-ab7ccc734ae03b00fe882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Negative-QTOFsplash10-004i-0900000000-ab7ccc734ae03b00fe882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Negative-QTOFsplash10-004i-0900000000-ab7ccc734ae03b00fe882021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028355
KNApSAcK IDNot Available
Chemspider ID148991
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound170404
PDB IDNot Available
ChEBI ID63905
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. Lanza DL, Code E, Crespi CL, Gonzalez FJ, Yost GS: Specific dehydrogenation of 3-methylindole and epoxidation of naphthalene by recombinant human CYP2F1 expressed in lymphoblastoid cells. Drug Metab Dispos. 1999 Jul;27(7):798-803. [PubMed:10383923 ]