FRCD

Common Name	Azulene(F03772)
2D Structure
Description	Azulene 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	F03772
CAS Number	275-51-4
PubChem CID	9231
Formula	C10H8
IUPAC Name	azulene
InChI Key	CUFNKYGDVFVPHO-UHFFFAOYSA-N
InChI	InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
Canonical SMILES	C1=CC=C2C=CC=C2C=C1
Isomeric SMILES	C1=CC=C2C=CC=C2C=C1
Wikipedia	Azulene
Synonyms	Bicyclo(5.3.0)decapentaene azulene 275-51-4 Cyclopentacycloheptene Azunamic Bicyclo[5.3.0]decapentaene azulen UNII-82R6M9MGLP Bicyclo(5.3.0)-1,3,5,7,9-decapentaene EINECS 205-993-6
Classifies	Pollutant
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Hydrocarbons
Class	Unsaturated hydrocarbons
Subclass	Olefins
Intermediate Tree Nodes	Cyclic olefins
Direct Parent	Azulenes
Alternative Parents	Polycyclic hydrocarbons Aromatic hydrocarbons
Molecular Framework	Aromatic homopolycyclic compounds
Substituents	Azulene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Aromatic homopolycyclic compound
Description	This compound belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.

Property Name	Property Value
Molecular Weight	128.174
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Complexity	94.6
Monoisotopic Mass	128.063
Exact Mass	128.063
XLogP	3.2
Formal Charge	0
Heavy Atom Count	10
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+	0.9835
Human Intestinal Absorption	HIA+	0.9959
Caco-2 Permeability	Caco2+	0.7223
P-glycoprotein Substrate	Non-substrate	0.8045
P-glycoprotein Inhibitor	Non-inhibitor	0.9523
P-glycoprotein Inhibitor	Non-inhibitor	0.9684
Renal Organic Cation Transporter	Non-inhibitor	0.8708
Distribution
Subcellular localization	Lysosome	0.8833
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8431
CYP450 2D6 Substrate	Non-substrate	0.8595
CYP450 3A4 Substrate	Non-substrate	0.7581
CYP450 1A2 Inhibitor	Non-inhibitor	0.6815
CYP450 2C9 Inhibitor	Non-inhibitor	0.9421
CYP450 2D6 Inhibitor	Non-inhibitor	0.9128
CYP450 2C19 Inhibitor	Non-inhibitor	0.9206
CYP450 3A4 Inhibitor	Non-inhibitor	0.9479
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.8490
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9684
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9546
AMES Toxicity	AMES toxic	0.5133
Carcinogens	Non-carcinogens	0.6807
Fish Toxicity	High FHMT	0.8676
Tetrahymena Pyriformis Toxicity	High TPT	0.9622
Honey Bee Toxicity	High HBT	0.8276
Biodegradation	Not ready biodegradable	0.5447
Acute Oral Toxicity	III	0.8232
Carcinogenicity (Three-class)	Warning	0.4807

Model	Value	Unit
Absorption
Aqueous solubility	-4.3727	LogS
Caco-2 Permeability	1.7209	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.5956	LD50, mol/kg
Fish Toxicity	1.0924	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	0.1979	pIGC50, ug/L

Title	Journal	Date	Pubmed ID
Prediction of polycyclic aromatic hydrocarbons toxicity using equilibrium partitioning approach and narcosis model.	Bull Environ Contam Toxicol	2010 Sep	20676606

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 ]