FRCD

Common Name	Acenaphthylene(F03758)
2D Structure
Description	Acenaphthylene 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 ID	F03758
CAS Number	208-96-8
PubChem CID	9161
Formula	C12H8
IUPAC Name	acenaphthylene
InChI Key	HXGDTGSAIMULJN-UHFFFAOYSA-N
InChI	InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H
Canonical SMILES	C1=CC2=C3C(=C1)C=CC3=CC=C2
Isomeric SMILES	C1=CC2=C3C(=C1)C=CC3=CC=C2
Wikipedia	Acenaphthylene
Synonyms	ACENAPHTHYLENE EINECS 205-917-1 208-96-8 Acenaphthalene Cyclopenta[de]naphthalene Cyclopenta(de)naphthalene HSDB 2661 UNII-1Z25C36811 NSC 59821 CHEBI:33081
Classifies	Pollutant
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Acenaphthylenes
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Acenaphthylenes
Alternative Parents	Polycyclic hydrocarbons Cyclic olefins Aromatic hydrocarbons
Molecular Framework	Aromatic homopolycyclic compounds
Substituents	Acenaphthylene - Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Cyclic olefin - Unsaturated hydrocarbon - Olefin - Hydrocarbon - Aromatic homopolycyclic compound
Description	This compound belongs to the class of organic compounds known as acenaphthylenes. These are aromatic polycyclic compounds containing an acenaphthylene moiety. Acenaphthylene is a carbotricyclic compound, consisting of a naphthalene with positions C1 and C8 connected by an ethylene bridge.

Property Name	Property Value
Molecular Weight	152.196
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Complexity	184
Monoisotopic Mass	152.063
Exact Mass	152.063
XLogP	3.7
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+	0.9801
Human Intestinal Absorption	HIA+	1.0000
Caco-2 Permeability	Caco2+	0.7787
P-glycoprotein Substrate	Non-substrate	0.7486
P-glycoprotein Inhibitor	Non-inhibitor	0.8823
P-glycoprotein Inhibitor	Non-inhibitor	0.9151
Renal Organic Cation Transporter	Non-inhibitor	0.8023
Distribution
Subcellular localization	Lysosome	0.7258
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7878
CYP450 2D6 Substrate	Non-substrate	0.8968
CYP450 3A4 Substrate	Non-substrate	0.7453
CYP450 1A2 Inhibitor	Inhibitor	0.7893
CYP450 2C9 Inhibitor	Non-inhibitor	0.7644
CYP450 2D6 Inhibitor	Non-inhibitor	0.8605
CYP450 2C19 Inhibitor	Inhibitor	0.5205
CYP450 3A4 Inhibitor	Non-inhibitor	0.8030
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.7643
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9265
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9212
AMES Toxicity	AMES toxic	0.9161
Carcinogens	Non-carcinogens	0.7284
Fish Toxicity	High FHMT	0.9893
Tetrahymena Pyriformis Toxicity	High TPT	0.9994
Honey Bee Toxicity	High HBT	0.8276
Biodegradation	Not ready biodegradable	0.9322
Acute Oral Toxicity	III	0.8000
Carcinogenicity (Three-class)	Warning	0.4026

Model	Value	Unit
Absorption
Aqueous solubility	-6.5518	LogS
Caco-2 Permeability	1.8216	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.8107	LD50, mol/kg
Fish Toxicity	-0.5586	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.4828	pIGC50, ug/L

Title	Journal	Date	Pubmed ID
Polycyclic aromatic hydrocarbons in fruits and vegetables: Origin, analysis, and occurrence.	Environ Pollut	2018 Mar	29172043
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

Targets

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 ]

General Function:: Zinc ion binding
Specific Function:: Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
Gene Name:: NR1I3
Uniprot ID:: Q14994
Molecular Weight:: 39942.145 Da

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 ]

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 ]