T3DB: Thiazolidine, 2-(nitromethylene)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (5)XML

Targets (5)

Record Information

Version

2.0

Creation Date

2009-06-18 21:54:32 UTC

Update Date

2014-12-24 20:23:06 UTC

Accession Number

T3D1053

Identification

Common Name

Thiazolidine, 2-(nitromethylene)

Class

Small Molecule

Description

Aromatic heterocycle containing a nitromethylene substituent. Fast acting neurotoxicant, effective both by contact or oral ingestion; they are relatively safe to vertebrates and degrade rapidly in the environment. (1)

Compound Type

Amine
Ether
Nitromethylene
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-(Nitromethylene)thiazolidine
2-[(E)-nitromethylidene]-1,3-thiazolane

Chemical Formula

C₄H₆N₂O₂S

Average Molecular Mass

146.168 g/mol

Monoisotopic Mass

146.015 g/mol

CAS Registry Number

94662-61-0

IUPAC Name

(2E)-2-(nitromethylidene)-1,3-thiazolidine

Traditional Name

(2E)-2-(nitromethylidene)-1,3-thiazolidine

SMILES

[H]\C(=C1\NCCS1)N(=O)=O

InChI Identifier

InChI=1S/C4H6N2O2S/c7-6(8)3-4-5-1-2-9-4/h3,5H,1-2H2/b4-3+

InChI Key

InChIKey=IDEZECZCLMOIJN-ONEGZZNKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thiazolidines. These are heterocyclic compounds containing a five-member saturated aliphatic ring with one nitrogen atom, one sulfur atom, three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Thiazolidines

Direct Parent

Thiazolidines

Alternative Parents

Substituents

Thiazolidine
C-nitro compound
Organic nitro compound
Secondary aliphatic amine
Organic oxoazanium
Secondary amine
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.18 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	0.48	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	1.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.98 m³·mol⁻¹	ChemAxon
Polarizability	12.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-e466014f2309017d59ee	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-74306c72aab4d7d89b36	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-41431f80f188d07019c9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-2900000000-a5cb5d1f57539caa9432	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01pk-5900000000-62e2e90fc618ba2521e5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9000000000-105ff81c00852776d3d7	2016-08-03	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (1)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Nitromethylenes are used as pesticides. (1)

Minimum Risk Level

Not Available

Health Effects

Nitromethylenes are neurotoxic. (1)

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

6455311

ChEMBL ID

CHEMBL2270159

ChemSpider ID

4957581

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Thiazolidine, 2-(nitromethylene)

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D1053.pdf

General References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Acetylcholine receptor subunit beta

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNB1
Uniprot ID:: P11230
Molecular Weight:: 56697.9 Da

References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Target Details

2. Neuronal acetylcholine receptor subunit alpha-3

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNA3
Uniprot ID:: P32297
Molecular Weight:: 57479.54 Da

References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Target Details

3. Neuronal acetylcholine receptor subunit alpha-4

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:: CHRNA4
Uniprot ID:: P43681
Molecular Weight:: 69956.47 Da

References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Target Details

4. Neuronal acetylcholine receptor subunit alpha-5

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:: CHRNA5
Uniprot ID:: P30532
Molecular Weight:: 53053.965 Da

References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Target Details

5. Neuronal acetylcholine receptor subunit beta-2

General Function:: Ligand-gated ion channel activity
Specific Function:: After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
Gene Name:: CHRNB2
Uniprot ID:: P17787
Molecular Weight:: 57018.575 Da

References

Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

Thiazolidine, 2-(nitromethylene) (T3D1053)

Structure for T3D1053: Thiazolidine, 2-(nitromethylene)

Targets

References

References

References

References

References