FRCD

Common Name	Anthanthrene(F03769)
2D Structure
Description	Anthanthrene 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	F03769
CAS Number	191-26-4
PubChem CID	9118
Formula	C22H12
IUPAC Name	None
InChI Key	YFIJJNAKSZUOLT-UHFFFAOYSA-N
InChI	InChI=1S/C22H12/c1-3-13-7-9-18-12-16-6-2-4-14-8-10-17-11-15(5-1)19(13)21(18)22(17)20(14)16/h1-12H
Canonical SMILES	C1=CC2=C3C(=C1)C=C4C=CC5=C6C4=C3C(=CC6=CC=C5)C=C2
Isomeric SMILES	C1=CC2=C3C(=C1)C=C4C=CC5=C6C4=C3C(=CC6=CC=C5)C=C2
Synonyms	Dibenzo[def,mno]chrysene Anthanthrene Anthranthrene Anthanthren 191-26-4 Dibenzo(cd,jk)pyrene Dibenzo[cd,jk]pyrene Anthanthren [German] CCRIS 48 UNII-L65OZG189H
Classifies	Pollutant
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Pyrenes
Subclass	Benzopyrenes
Intermediate Tree Nodes	Not available
Direct Parent	Benzopyrenes
Alternative Parents	Polycyclic hydrocarbons Unsaturated hydrocarbons Aromatic hydrocarbons Anthracenes Chrysenes
Molecular Framework	Aromatic homopolycyclic compounds
Substituents	Benzo-a-pyrene - Chrysene - Phenanthrene - Anthracene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
Description	This compound belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.

Property Name	Property Value
Molecular Weight	276.338
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Complexity	411
Monoisotopic Mass	276.094
Exact Mass	276.094
XLogP	6.7
Formal Charge	0
Heavy Atom Count	22
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+	0.9728
Human Intestinal Absorption	HIA+	1.0000
Caco-2 Permeability	Caco2+	0.8537
P-glycoprotein Substrate	Non-substrate	0.7437
P-glycoprotein Inhibitor	Non-inhibitor	0.9276
P-glycoprotein Inhibitor	Non-inhibitor	0.9361
Renal Organic Cation Transporter	Non-inhibitor	0.8178
Distribution
Subcellular localization	Lysosome	0.8244
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8091
CYP450 2D6 Substrate	Non-substrate	0.8874
CYP450 3A4 Substrate	Non-substrate	0.7722
CYP450 1A2 Inhibitor	Inhibitor	0.6798
CYP450 2C9 Inhibitor	Non-inhibitor	0.9070
CYP450 2D6 Inhibitor	Non-inhibitor	0.9231
CYP450 2C19 Inhibitor	Non-inhibitor	0.8548
CYP450 3A4 Inhibitor	Non-inhibitor	0.9288
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.5335
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9317
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9054
AMES Toxicity	AMES toxic	0.9118
Carcinogens	Non-carcinogens	0.7059
Fish Toxicity	High FHMT	0.9391
Tetrahymena Pyriformis Toxicity	High TPT	0.9959
Honey Bee Toxicity	High HBT	0.7822
Biodegradation	Not ready biodegradable	0.8151
Acute Oral Toxicity	III	0.7913
Carcinogenicity (Three-class)	Warning	0.4954

Model	Value	Unit
Absorption
Aqueous solubility	-6.2526	LogS
Caco-2 Permeability	1.9501	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.9645	LD50, mol/kg
Fish Toxicity	0.5157	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.9399	pIGC50, ug/L

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:: 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 ]