N-Methylsaccharin

Details

• Internal ID: 3ed081ae-9b9b-4f85-8d71-efb2514a878b
• Taxonomy: Organoheterocyclic compounds > Benzothiazoles
• IUPAC Name: 2-methyl-1,1-dioxo-1,2-benzothiazol-3-one
• SMILES (Canonical): CN1C(=O)C2=CC=CC=C2S1(=O)=O
• SMILES (Isomeric): CN1C(=O)C2=CC=CC=C2S1(=O)=O
• InChI: InChI=1S/C8H7NO3S/c1-9-8(10)6-4-2-3-5-7(6)13(9,11)12/h2-5H,1H3
• InChI Key: DDIIAJRLFATEEE-UHFFFAOYSA-N
• Popularity: 35 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₇NO₃S
• Molecular Weight: 197.21 g/mol
• Exact Mass: 197.01466426 g/mol
• Topological Polar Surface Area (TPSA): 62.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• RefChem:474754
• N-Methylsaccharin
• 15448-99-4
• 2-Methylbenzo[d]isothiazol-3(2H)-one 1,1-dioxide
• 2-methyl-1,1-dioxo-1,2-benzothiazol-3-one
• MFCD00059263
• NSC 39120
• T63VBY3AYH
• CHEMBL131790
• 2-methyl-1,2-benzothiazol-3(2H)-one 1,1-dioxide
• NSC-39120
• 1,2-Benzisothiazolin-3-one, 2-methyl-, 1,1-dioxide
• 2-Methyl-1,2-benzisothiazole-3(2H)-one-1,1-dioxide
• 1,2-Benzisothiazol-3(2H)-one, 2-methyl-, 1,1-dioxide
• UNII-T63VBY3AYH
• Methylsaccharin
• methyl saccharine
• NSC39120
• EINECS 239-466-7
• AI3-23674
• 2-Methyl-1,1-dioxide
• triflusulfuron-methyl TP1
• SCHEMBL107126
• SCHEMBL30339085
• 1, 2-methyl-, 1,1-dioxide
• DTXSID10165639
• BDBM50496471
• STL293362
• AKOS016011169
• DS-6404
• SY053783
• DB-007773
• CS-0151203
• M0427
• NS00025020
• 2-methyl-1,1-dioxo-benzo[d]isothiazol-3-one
• D78426
• F319824
• Q27289719
• 2-methyl-2,3-dihydro-1,2-benzothiazole-1,1,3-trione
• 2-methyl-2,3-dihydro-1lambda,2-benzothiazole-1,1,3-trione
• 2-Methyl-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	+	0.8843	88.43%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5124	51.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9585	95.85%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9646	96.46%
P-glycoprotein inhibitior	-	0.9924	99.24%
P-glycoprotein substrate	-	0.9527	95.27%
CYP3A4 substrate	-	0.5943	59.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8223	82.23%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.8510	85.10%
CYP2C19 inhibition	-	0.7878	78.78%
CYP2D6 inhibition	-	0.9169	91.69%
CYP1A2 inhibition	-	0.8118	81.18%
CYP2C8 inhibition	-	0.9888	98.88%
CYP inhibitory promiscuity	-	0.9251	92.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6051	60.51%
Carcinogenicity (trinary)	Non-required	0.6923	69.23%
Eye corrosion	-	0.9581	95.81%
Eye irritation	+	0.8335	83.35%
Skin irritation	-	0.7488	74.88%
Skin corrosion	-	0.8714	87.14%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7852	78.52%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8638	86.38%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.5191	51.91%
Nephrotoxicity	+	0.6952	69.52%
Acute Oral Toxicity (c)	III	0.6958	69.58%
Estrogen receptor binding	-	0.9605	96.05%
Androgen receptor binding	-	0.6481	64.81%
Thyroid receptor binding	-	0.6955	69.55%
Glucocorticoid receptor binding	-	0.9097	90.97%
Aromatase binding	-	0.8408	84.08%
PPAR gamma	-	0.8282	82.82%
Honey bee toxicity	-	0.9696	96.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.9010	90.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL205	P00918	Carbonic anhydrase II	2600 nM	Ki	PMID: 24560739
CHEMBL3594	Q16790	Carbonic anhydrase IX	400 nM; 400 nM	Ki; Ki	PMID: 24560739; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.85%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.56%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.22%	82.69%
CHEMBL4208	P20618	Proteasome component C5	85.69%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.39%	93.65%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.03%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.28%	86.33%

Plants that contains it

• Psammosilene tunicoides

Cross-Links

• PubChem: 27290
• NPASS: NPC181390
• ChEMBL: CHEMBL131790