FRCD

Common Name	2(3H)-Benzothiazolethione(F05558)
2D Structure
Description	2(3H)-Benzothiazolethione is found in fruits. 2(3H)-Benzothiazolethione is a constituent of cranberries. 2(3H)-Benzothiazolethione belongs to the family of Benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-member ring with four carbon atoms, one nitrogen atom and one sulfur atom).
FRCD ID	F05558
CAS Number	149-30-4
PubChem CID	21831736
Formula	C14H10N2S4
IUPAC Name	3H-1,3-benzothiazole-2-thione
InChI Key	JYRPXJDQMBHLOJ-UHFFFAOYSA-N
InChI	InChI=1S/2C7H5NS2/c29-7-8-5-3-1-2-4-6(5)10-7/h21-4H,(H,8,9)
Canonical SMILES	C1=CC=C2C(=C1)NC(=S)S2.C1=CC=C2C(=C1)NC(=S)S2
Isomeric SMILES	C1=CC=C2C(=C1)NC(=S)S2.C1=CC=C2C(=C1)NC(=S)S2
Synonyms	SCHEMBL3789760
Classifies	Plant Toxin
Update Date	Nov 13, 2018 17:07

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Class	Benzothiazoles
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Benzothiazoles
Alternative Parents	Hydrocarbon derivatives Organonitrogen compounds Heteroaromatic compounds Azacyclic compounds Organosulfur compounds Thiazoles
Molecular Framework	Not available
Substituents	1,3-benzothiazole - Benzenoid - Heteroaromatic compound - Thiazole - Azole - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aromatic heteropolycyclic compound
Description	This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Property Name	Property Value
Molecular Weight	334.488
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Complexity	158
Monoisotopic Mass	333.973
Exact Mass	333.973
Formal Charge	0
Heavy Atom Count	20
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	2

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9639
Human Intestinal Absorption	HIA+	0.9887
Caco-2 Permeability	Caco2-	0.6458
P-glycoprotein Substrate	Non-substrate	0.7550
P-glycoprotein Inhibitor	Non-inhibitor	0.7598
P-glycoprotein Inhibitor	Non-inhibitor	0.7207
Renal Organic Cation Transporter	Non-inhibitor	0.7742
Distribution
Subcellular localization	Mitochondria	0.4808
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8336
CYP450 2D6 Substrate	Non-substrate	0.8399
CYP450 3A4 Substrate	Non-substrate	0.7878
CYP450 1A2 Inhibitor	Inhibitor	0.9098
CYP450 2C9 Inhibitor	Non-inhibitor	0.5339
CYP450 2D6 Inhibitor	Non-inhibitor	0.6364
CYP450 2C19 Inhibitor	Inhibitor	0.8836
CYP450 3A4 Inhibitor	Inhibitor	0.5981
CYP Inhibitory Promiscuity	High CYP Inhibitory Promiscuity	0.9742
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.9822
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8386
AMES Toxicity	Non AMES toxic	0.5771
Carcinogens	Non-carcinogens	0.9017
Fish Toxicity	High FHMT	0.9769
Tetrahymena Pyriformis Toxicity	High TPT	0.9731
Honey Bee Toxicity	High HBT	0.6285
Biodegradation	Not ready biodegradable	1.0000
Acute Oral Toxicity	III	0.5284
Carcinogenicity (Three-class)	Non-required	0.4712

Model	Value	Unit
Absorption
Aqueous solubility	-4.4523	LogS
Caco-2 Permeability	1.1539	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	2.2087	LD50, mol/kg
Fish Toxicity	1.1197	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.3387	pIGC50, ug/L

Targets

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular Weight:: 56277.81 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:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular Weight:: 55930.545 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

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 ]