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Record Information
Version2.0
Creation Date2014-09-11 05:17:58 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4819
Identification
Common NameIndene
ClassSmall Molecule
DescriptionIndene is a flammable polycyclic hydrocarbon. It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins.
Compound Type
  • Industrial/Workplace Toxin
  • Organic Compound
  • Plastic
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H8
Average Molecular Mass116.160 g/mol
Monoisotopic Mass116.063 g/mol
CAS Registry Number95-13-6
IUPAC Name1H-indene
Traditional Nameindene
SMILESC1C=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChI KeyInChIKey=YBYIRNPNPLQARY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndenes and isoindenes
Sub ClassNot Available
Direct ParentIndenes and isoindenes
Alternative Parents
Substituents
  • Indene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-1.8°C
Boiling Point182°C
SolubilityNot Available
LogP2.92
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP3.04ALOGPS
logP2.7ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)19.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.06 m³·mol⁻¹ChemAxon
Polarizability13.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-31c6bafe38ab442d08f8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-57e7cee21ad28cdacc8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-de44d429371251a8a9cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9700000000-8adf700cc89eba140b38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c11d9f2f09e173f6fa26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-c11d9f2f09e173f6fa26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-97c05b03c31796724c95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c1ac08a3831a2d9a5c97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-7900000000-21a91334a3cd4391431dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-3137f4ab05eca7bc0e44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-18f4dfd7bbdd9c9f9a40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-18f4dfd7bbdd9c9f9a40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-3c5095f7757fb2bda6ecJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-014i-3900000000-933405a618c9308220baJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is composed of a benzene ring fused with a cyclopentene ring.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02815
HMDB IDNot Available
PubChem Compound ID7219
ChEMBL IDNot Available
ChemSpider ID6949
KEGG IDC11565
UniProt IDNot Available
OMIM ID
ChEBI ID33051
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkIndene
References
Synthesis Reference

Hisatake Sato, Masaharu Makino, “Method for preparing light-colored indene-coumarone resin.” U.S. Patent US4946915, issued July, 1930.

MSDST3D4819.pdf
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.18 uMATG_PXR_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]