1-S-[(1Z)-N-(sulfonatooxy)pent-4-enimidoyl]-1-thio-beta-D-glucopyranose

Details

• Internal ID: 7bba2b6e-05fb-4b0e-a68a-fc0cd7c6fa23
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glucosinolates > Alkylglucosinolates
• IUPAC Name: [(Z)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpent-4-enylideneamino] sulfate
• SMILES (Canonical): C=CCCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): C=CCC/C(=N/OS(=O)(=O)[O-])/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/p-1/b12-7-/t6-,8-,9+,10-,11+/m1/s1
• InChI Key: PLYQBXHVYUJNQB-IIPHORNXSA-M
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₈NO₉S₂-
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.04229850 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.72
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 1-S-[(1Z)-N-(sulfonatooxy)pent-4-enimidoyl]-1-thio-beta-D-glucopyranose
• CHEBI:5411
• N-(Sulfonatooxy)-4-pentenimidothioic acid beta-D-glucopyranosyl ester
• [(Z)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpent-4-enylideneamino] sulfate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7645	76.45%
Caco-2	-	0.9141	91.41%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4089	40.89%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8719	87.19%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9335	93.35%
P-glycoprotein inhibitior	-	0.8654	86.54%
P-glycoprotein substrate	-	0.9152	91.52%
CYP3A4 substrate	+	0.5432	54.32%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.9528	95.28%
CYP2C9 inhibition	-	0.7089	70.89%
CYP2C19 inhibition	-	0.6768	67.68%
CYP2D6 inhibition	-	0.8607	86.07%
CYP1A2 inhibition	-	0.6679	66.79%
CYP2C8 inhibition	-	0.8272	82.72%
CYP inhibitory promiscuity	-	0.9475	94.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5637	56.37%
Carcinogenicity (trinary)	Non-required	0.5418	54.18%
Eye corrosion	-	0.9668	96.68%
Eye irritation	-	0.9458	94.58%
Skin irritation	-	0.7530	75.30%
Skin corrosion	-	0.8926	89.26%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4265	42.65%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.7321	73.21%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6459	64.59%
Acute Oral Toxicity (c)	III	0.5665	56.65%
Estrogen receptor binding	-	0.5447	54.47%
Androgen receptor binding	-	0.6915	69.15%
Thyroid receptor binding	-	0.6389	63.89%
Glucocorticoid receptor binding	-	0.5984	59.84%
Aromatase binding	-	0.5464	54.64%
PPAR gamma	+	0.6005	60.05%
Honey bee toxicity	+	0.5455	54.55%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.4180	41.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	97.45%	83.57%
CHEMBL226	P30542	Adenosine A1 receptor	94.73%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.14%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.18%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.05%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.99%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.01%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.56%	96.95%
CHEMBL2581	P07339	Cathepsin D	82.78%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.50%	96.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.50%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.35%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.93%	95.83%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	81.62%	92.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.82%	95.89%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.43%	96.09%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.06%	92.32%

Plants that contains it

• Isatis tinctoria
• Persicaria tinctoria

Cross-Links

• PubChem: 20843338
• NPASS: NPC114975