FRCD

Common Name	Acenaphthene(F03397)
2D Structure
Description	Acenaphthene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning of organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (L10)
FRCD ID	F03397
CAS Number	83-32-9
PubChem CID	6734
Formula	C12H10
IUPAC Name	1,2-dihydroacenaphthylene
InChI Key	CWRYPZZKDGJXCA-UHFFFAOYSA-N
InChI	InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2
Canonical SMILES	C1CC2=CC=CC3=C2C1=CC=C3
Isomeric SMILES	C1CC2=CC=CC3=C2C1=CC=C3
Wikipedia	Acenaphthene
Synonyms	1,8-Ethylenenaphthalene 1,8-Dihydroacenaphthalene ACENAPHTHENE 1,2-Dihydroacenaphthylene 83-32-9 Naphthyleneethylene peri-Ethylenenaphthalene Acenaphthylene, 1,2-dihydro- Ethylenenaphthalene UNII-V8UT1GAC5Y
Classifies	Pollutant
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Naphthalenes
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Naphthalenes
Alternative Parents	Polycyclic hydrocarbons Unsaturated hydrocarbons
Molecular Framework	Aromatic homopolycyclic compounds
Substituents	Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
Description	This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Property Name	Property Value
Molecular Weight	154.212
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Complexity	155
Monoisotopic Mass	154.078
Exact Mass	154.078
XLogP	3.9
Formal Charge	0
Heavy Atom Count	12
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9786
Human Intestinal Absorption	HIA+	1.0000
Caco-2 Permeability	Caco2+	0.7754
P-glycoprotein Substrate	Non-substrate	0.7572
P-glycoprotein Inhibitor	Non-inhibitor	0.8713
P-glycoprotein Inhibitor	Non-inhibitor	0.9095
Renal Organic Cation Transporter	Non-inhibitor	0.7255
Distribution
Subcellular localization	Lysosome	0.7726
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8014
CYP450 2D6 Substrate	Non-substrate	0.8435
CYP450 3A4 Substrate	Non-substrate	0.7268
CYP450 1A2 Inhibitor	Inhibitor	0.6978
CYP450 2C9 Inhibitor	Non-inhibitor	0.8775
CYP450 2D6 Inhibitor	Non-inhibitor	0.8845
CYP450 2C19 Inhibitor	Non-inhibitor	0.7473
CYP450 3A4 Inhibitor	Non-inhibitor	0.9025
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.5649
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.8843
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8604
AMES Toxicity	AMES toxic	0.8933
Carcinogens	Non-carcinogens	0.8120
Fish Toxicity	High FHMT	0.9392
Tetrahymena Pyriformis Toxicity	High TPT	0.9973
Honey Bee Toxicity	High HBT	0.7606
Biodegradation	Not ready biodegradable	0.7808
Acute Oral Toxicity	III	0.7135
Carcinogenicity (Three-class)	Warning	0.4287

Model	Value	Unit
Absorption
Aqueous solubility	-6.4064	LogS
Caco-2 Permeability	1.8294	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.2702	LD50, mol/kg
Fish Toxicity	0.3632	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.2705	pIGC50, ug/L

Title	Journal	Date	Pubmed ID
Polycyclic aromatic hydrocarbons in fruits and vegetables: Origin, analysis, and occurrence.	Environ Pollut	2018 Mar	29172043
Polycyclic aromatic hydrocarbons and trace metals in mosque's carpet dust ofRiyadh, Saudi Arabia, and their health risk implications.	Environ Sci Pollut Res Int	2016 Nov	27497850
Polycyclic aromatic hydrocarbons in Haliotis tuberculata (Linnaeus, 1758)(Mollusca, Gastropoda): Considerations on food safety and source investigation.	Food Chem Toxicol	2016 Aug	27235950
[Preparation method of stalk environmental biomaterial and its sorption abilityfor polycyclic aromatic hydrocarbons in water].	Huan Jing Ke Xue	2011 Jan	21404677
Halogenated POPs and PAHs in blood plasma of Hong Kong residents.	Environ Sci Technol	2011 Feb 15	21207933
Analysis of polycyclic aromatic hydrocarbons in fish: evaluation of a quick,easy, cheap, effective, rugged, and safe extraction method.	J Sep Sci	2009 Oct	19750509
Assessment of hydrocarbons concentration in marine fauna due to Tasman Spirit oil spill along the Clifton beach at Karachi coast.	Environ Monit Assess	2009 Jan	18302003
Detection of polycyclic aromatic hydrocarbon levels in milk collected nearpotential contamination sources.	J Agric Food Chem	2002 Jul 31	12137489

Targets

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.

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 ]

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.

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 ]