VINYL ACETATE

General Information

From www.fda.gov

2D Structure
CID	7904
IUPAC Name	ethenyl acetate
InChI	InChI=1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3
InChI Key	XTXRWKRVRITETP-UHFFFAOYSA-N
Canonical SMILES	CC(=O)OC=C
Molecular Formula	C4H6O2
Wikipedia	polyvinyl acetate

From Pubchem

Property Name	Property Value
Molecular Weight	86.09
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Complexity	65.9
CACTVS Substructure Key Fingerprint	A A A D c Y B g M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A A A C g g A I C C A A A B A C I A A C S C A A A C A A A A A A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	26.3
Monoisotopic Mass	86.037
Exact Mass	86.037
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	6
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

From Pubchem

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9794
Human Intestinal Absorption	HIA+	0.9924
Caco-2 Permeability	Caco2+	0.6354
P-glycoprotein Substrate	Non-substrate	0.8262
P-glycoprotein Inhibitor	Non-inhibitor	0.9155
P-glycoprotein Inhibitor	Non-inhibitor	0.9518
Renal Organic Cation Transporter	Non-inhibitor	0.9300
Distribution
Subcellular localization	Mitochondria	0.4999
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8060
CYP450 2D6 Substrate	Non-substrate	0.9433
CYP450 3A4 Substrate	Non-substrate	0.7576
CYP450 1A2 Inhibitor	Non-inhibitor	0.8332
CYP450 2C9 Inhibitor	Non-inhibitor	0.9274
CYP450 2D6 Inhibitor	Non-inhibitor	0.9714
CYP450 2C19 Inhibitor	Non-inhibitor	0.9202
CYP450 3A4 Inhibitor	Non-inhibitor	0.9374
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.9238
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9644
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9860
AMES Toxicity	Non AMES toxic	0.9174
Carcinogens	Carcinogens	0.6715
Fish Toxicity	High FHMT	0.9382
Tetrahymena Pyriformis Toxicity	Low TPT	0.6157
Honey Bee Toxicity	High HBT	0.8718
Biodegradation	Ready biodegradable	0.7560
Acute Oral Toxicity	III	0.7843
Carcinogenicity (Three-class)	Non-required	0.5626

From admetSAR

Model	Value	Unit
Absorption
Aqueous solubility	-0.7516	LogS
Caco-2 Permeability	1.3111	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.8702	LD50, mol/kg
Fish Toxicity	0.3980	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	-0.5046	pIGC50, ug/L

From admetSAR

Route of Exposure	Oral ; inhalation ; dermal
Mechanism of Toxicity	One of the metabolites of vinyl acetate, acetaldehyde, is a known animal carcinogen. Acetaldehyde can form adducts with DNA, causing damage such as cross-links.
Metabolism	Vinyl acetate may be absorbed following ingestion, inhalation, or dermal exposure, and distributes throughout the body. It is rapidly hydrolyzed by esterases in the blood to acetate and the unstable intermediate, vinyl alcohol. Vinyl alcohol is then rapidly converted to acetaldehyde, which in turn is metabolized to acetate in the liver. This in turn is incorporated into the "2 carbon pool" of normal body metabolism and eventually forms carbon dioxide as the major breakdown product, which is expired.
Toxicity Values	LD50: 2.92 g/kg (Oral, Rat) LC50: 2511 ppm over 4 hours (Inhalation, Rabbit)
Lethal Dose
Carcinogenicity (IARC Classification)	2B, possibly carcinogenic to humans.
Minimum Risk Level	Intermediate Inhalation: 0.01 ppm
Health Effects	Vinyl acetate may affect the immune system. It may also be a carcinogen. (L1304)
Treatment
Reference	Brooks PJ, Theruvathu JA: DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Alcohol. 2005 Apr;35(3):187-93.[16054980 ]

From T3DB

Kingdom	Organic compounds
Superclass	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Subclass	Carboxylic acid derivatives
Intermediate Tree Nodes	Carboxylic acid esters
Direct Parent	Enol esters
Alternative Parents	Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Carbonyl compounds
Molecular Framework	Aliphatic acyclic compounds
Substituents	Enol ester - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as enol esters. These are ester derivatives of enols. They have the general formula RC=COC(=O)R' where R, R' = H or organyl group.

From ClassyFire

General Function:: Temperature-gated cation channel activity
Specific Function:: Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:: TRPA1
Uniprot ID:: O75762
Molecular Weight:: 127499.88 Da

Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]

From T3DB