Fluorene

Basic Info

Common NameFluorene(F03763)
2D Structure
Description

Fluorene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (L10)

FRCD IDF03763
CAS Number86-73-7
PubChem CID6853
FormulaC13H10
IUPAC Name

9H-fluorene

InChI Key

NIHNNTQXNPWCJQ-UHFFFAOYSA-N

InChI

InChI=1S/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2

Canonical SMILES

C1C2=CC=CC=C2C3=CC=CC=C31

Isomeric SMILES

C1C2=CC=CC=C2C3=CC=CC=C31

Synonyms
        
            o-Biphenylenemethane
        
            FLUORENE
        
            9H-Fluorene
        
            86-73-7
        
            Diphenylenemethane
        
            2,3-Benzindene
        
            2,2'-Methylenebiphenyl
        
            o-Biphenylmethane
        
            Methane, diphenylene-
        
            Fluoren
Classifies
                

                  
                    Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassFluorenes
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentFluorenes
Alternative Parents
Molecular FrameworkAromatic homopolycyclic compounds
SubstituentsFluorene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Properties

Property NameProperty Value
Molecular Weight166.223
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Complexity165
Monoisotopic Mass166.078
Exact Mass166.078
XLogP4.2
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9848
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7795
P-glycoprotein SubstrateNon-substrate0.7611
P-glycoprotein InhibitorNon-inhibitor0.8926
Non-inhibitor0.9519
Renal Organic Cation TransporterNon-inhibitor0.7999
Distribution
Subcellular localizationLysosome0.7333
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7989
CYP450 2D6 SubstrateNon-substrate0.8684
CYP450 3A4 SubstrateNon-substrate0.7639
CYP450 1A2 InhibitorInhibitor0.8047
CYP450 2C9 InhibitorNon-inhibitor0.6504
CYP450 2D6 InhibitorNon-inhibitor0.7662
CYP450 2C19 InhibitorNon-inhibitor0.5184
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6841
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9560
Non-inhibitor0.8676
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.7763
Fish ToxicityHigh FHMT0.9528
Tetrahymena Pyriformis ToxicityHigh TPT0.9975
Honey Bee ToxicityHigh HBT0.7511
BiodegradationNot ready biodegradable0.7808
Acute Oral ToxicityIII0.7918
Carcinogenicity (Three-class)Warning0.3871
Model Value Unit
Absorption
Aqueous solubility-6.7426LogS
Caco-2 Permeability1.7942LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0363LD50, mol/kg
Fish Toxicity0.0092pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.3025pIGC50, ug/L

References

TitleJournalDatePubmed ID
Salicylyl Fluorene Derivatives as Fluorescent Sensors for Cu(II) Ions.J Fluoresc2016 Mar26753759
A new selective fluorene-based fluorescent internal charge transfer (ICT) sensor for sugar alcohols in aqueous solution.Anal Bioanal Chem2016 Mar26758597
Polycyclic aromatic hydrocarbons in Haliotis tuberculata (Linnaeus, 1758)(Mollusca, Gastropoda): Considerations on food safety and source investigation.Food Chem Toxicol2016 Aug27235950
Determination of polycyclic aromatic hydrocarbons in dry tea.J Environ Sci Health B201526065515
Antimutagenic evaluation of vitamins B1, B6 and B12 in vitro and in vivo, with the Ames test.Food Chem Toxicol2013 Mar23201371
Novel multifunctional acceptor phase additive of water-miscible ionic liquid inhollow-fiber protected liquid phase microextraction.Talanta2012 Jan 1522265467
Assessment of hydrocarbons concentration in marine fauna due to Tasman Spirit oil spill along the Clifton beach at Karachi coast.Environ Monit Assess2009 Jan18302003
Isolation and characterization of bacteria capable of degrading polycyclicaromatic hydrocarbons (PAHs) and organophosphorus pesticides fromPAH-contaminated soil in Hilo, Hawaii.J Agric Food Chem2007 Jul 1117552538
Detection of polycyclic aromatic hydrocarbon levels in milk collected nearpotential contamination sources.J Agric Food Chem2002 Jul 3112137489
Alterations in epidermal growth factor binding to hepatic membranes following dietary exposure of rats to known hepatocarcinogens.Toxicol Lett1997 Mar 149096280
Detoxification of polycyclic aromatic hydrocarbons by fungi.J Ind Microbiol1992 Jan1367975

Targets

Target Details

Glycine N-methyltransferase

General Function:
Glycine n-methyltransferase activity
Specific Function:
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular Weight:
32742.0 Da
Mechanism of Action:
Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
  1. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
Target Details

Aryl hydrocarbon receptor

General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
Mechanism of Action:
Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
  1. Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]