[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-2-(3-methoxyphenyl)-N-sulfooxyethanimidothioate

Details

• Internal ID: da15c28f-220d-433d-a916-1a2fe7d9fc21
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glucosinolates > Alkylglucosinolates
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-2-(3-methoxyphenyl)-N-sulfooxyethanimidothioate
• SMILES (Canonical): COC1=CC=CC(=C1)CC(=NOS(=O)(=O)O)SC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): COC1=CC=CC(=C1)C/C(=N\OS(=O)(=O)O)/S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C15H21NO10S2/c1-24-9-4-2-3-8(5-9)6-11(16-26-28(21,22)23)27-15-14(20)13(19)12(18)10(7-17)25-15/h2-5,10,12-15,17-20H,6-7H2,1H3,(H,21,22,23)/b16-11+/t10-,12-,13+,14-,15+/m1/s1
• InChI Key: RYDIUEJGEAUJAI-MFIRQCQASA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁NO₁₀S₂
• Molecular Weight: 439.50 g/mol
• Exact Mass: 439.06068821 g/mol
• Topological Polar Surface Area (TPSA): 209.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• Glucolimnanthin
• 111810-95-8
• [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-2-(3-methoxyphenyl)-N-sulfooxyethanimidothioate
• UNII-U4PL68V5CY
• beta-D-Glucopyranose, 1-thio-, 1-(3-methoxy-N-(sulfooxy)benzeneethanimidate)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6102	61.02%
Caco-2	-	0.8550	85.50%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4309	43.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5942	59.42%
P-glycoprotein inhibitior	-	0.7619	76.19%
P-glycoprotein substrate	-	0.7304	73.04%
CYP3A4 substrate	+	0.5922	59.22%
CYP2C9 substrate	-	0.8030	80.30%
CYP2D6 substrate	-	0.8202	82.02%
CYP3A4 inhibition	-	0.8646	86.46%
CYP2C9 inhibition	-	0.7106	71.06%
CYP2C19 inhibition	-	0.6602	66.02%
CYP2D6 inhibition	-	0.8615	86.15%
CYP1A2 inhibition	-	0.6393	63.93%
CYP2C8 inhibition	-	0.6231	62.31%
CYP inhibitory promiscuity	-	0.7860	78.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.5187	51.87%
Carcinogenicity (trinary)	Non-required	0.5581	55.81%
Eye corrosion	-	0.9653	96.53%
Eye irritation	-	0.9487	94.87%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.8890	88.90%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4904	49.04%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8249	82.49%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6244	62.44%
Acute Oral Toxicity (c)	III	0.5719	57.19%
Estrogen receptor binding	+	0.6060	60.60%
Androgen receptor binding	-	0.5173	51.73%
Thyroid receptor binding	-	0.5822	58.22%
Glucocorticoid receptor binding	-	0.4932	49.32%
Aromatase binding	+	0.5882	58.82%
PPAR gamma	+	0.5770	57.70%
Honey bee toxicity	-	0.7592	75.92%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5645	56.45%
Fish aquatic toxicity	-	0.3751	37.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.96%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.94%	95.93%
CHEMBL2581	P07339	Cathepsin D	97.89%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.46%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	96.00%	94.73%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	92.65%	95.55%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.90%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.43%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.21%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.14%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.10%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.10%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.98%	94.45%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.40%	99.18%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.09%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.97%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.66%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.01%	86.33%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	82.62%	88.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.37%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.10%	85.31%
CHEMBL2535	P11166	Glucose transporter	81.74%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.54%	99.17%

Plants that contains it

• Lepidium meyenii
• Limnanthes alba
• Limnanthes douglasii

Cross-Links

• PubChem: 9548725
• LOTUS: LTS0054922
• wikiData: Q105247497