FRCD

Common Name	2,3,4,5-Tetrachlorophenol(F03409)
2D Structure
Description	2,3,4,5-Tetrachlorophenol is one of several chlorophenol isomers. It is a solid with a strong medicinal taste and odor, and small amounts can be tasted in water. (L159)
FRCD ID	F03409
CAS Number	25167-83-3
PubChem CID	21013
Formula	C6H2Cl4O
IUPAC Name	2,3,4,5-tetrachlorophenol
InChI Key	RULKYXXCCZZKDZ-UHFFFAOYSA-N
InChI	InChI=1S/C6H2Cl4O/c7-2-1-3(11)5(9)6(10)4(2)8/h1,11H
Canonical SMILES	C1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)O
Isomeric SMILES	C1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)O
Synonyms	Phenol, tetrachloro- 2,3,4,5-TETRACHLOROPHENOL Tetrachlorophenol 4901-51-3 Phenol, 2,3,4,5-tetrachloro- 2,3,4,5-Tetrachlorophenate UNII-D2UW5NHW9J CCRIS 4722 HSDB 6765 EINECS 225-531-7
Classifies	Predicted: Pollutant
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Benzenoids
Class	Phenols
Subclass	Halophenols
Intermediate Tree Nodes	Chlorophenols
Direct Parent	P-chlorophenols
Alternative Parents	Hydrocarbon derivatives Organochlorides 1-hydroxy-2-unsubstituted benzenoids Organooxygen compounds Aryl chlorides Chlorobenzenes M-chlorophenols O-chlorophenols
Molecular Framework	Aromatic homomonocyclic compounds
Substituents	4-chlorophenol - 2-chlorophenol - 3-chlorophenol - 1-hydroxy-2-unsubstituted benzenoid - Halobenzene - Chlorobenzene - Monocyclic benzene moiety - Aryl halide - Aryl chloride - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.

Property Name	Property Value
Molecular Weight	231.881
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Complexity	143
Monoisotopic Mass	229.886
Exact Mass	231.883
XLogP	4.2
Formal Charge	0
Heavy Atom Count	11
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+	0.9643
Human Intestinal Absorption	HIA+	0.9932
Caco-2 Permeability	Caco2+	0.8943
P-glycoprotein Substrate	Non-substrate	0.8164
P-glycoprotein Inhibitor	Non-inhibitor	0.9782
P-glycoprotein Inhibitor	Non-inhibitor	0.9941
Renal Organic Cation Transporter	Non-inhibitor	0.8694
Distribution
Subcellular localization	Mitochondria	0.8731
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.7834
CYP450 2D6 Substrate	Non-substrate	0.8320
CYP450 3A4 Substrate	Non-substrate	0.6716
CYP450 1A2 Inhibitor	Inhibitor	0.8447
CYP450 2C9 Inhibitor	Non-inhibitor	0.6560
CYP450 2D6 Inhibitor	Non-inhibitor	0.9307
CYP450 2C19 Inhibitor	Inhibitor	0.5210
CYP450 3A4 Inhibitor	Non-inhibitor	0.8866
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.6737
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.8043
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.9426
AMES Toxicity	Non AMES toxic	0.9306
Carcinogens	Non-carcinogens	0.7562
Fish Toxicity	High FHMT	0.9126
Tetrahymena Pyriformis Toxicity	High TPT	0.9877
Honey Bee Toxicity	High HBT	0.7919
Biodegradation	Not ready biodegradable	0.8276
Acute Oral Toxicity	III	0.8688
Carcinogenicity (Three-class)	Non-required	0.6275

Model	Value	Unit
Absorption
Aqueous solubility	-2.2778	LogS
Caco-2 Permeability	1.8233	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.4130	LD50, mol/kg
Fish Toxicity	0.5640	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.5348	pIGC50, ug/L

Targets

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 ]

General Function:: Transmembrane transporter activity
Specific Function:: Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Subunits alpha and beta form the catalytic core in F(1). Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits. Subunit alpha does not bear the catalytic high-affinity ATP-binding sites (By similarity).
Gene Name:: ATP5A1
Uniprot ID:: P25705
Molecular Weight:: 59750.06 Da

Janik F, Wolf HU: The Ca(2+)-transport-ATPase of human erythrocytes as an in vitro toxicity test system--acute effects of some chlorinated compounds. J Appl Toxicol. 1992 Oct;12(5):351-8. [1447481 ]