4-[(3S,8R)-1,5-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxabicyclo[3.2.1]octan-8-yl]butan-2-one

Details

• Internal ID: 93016e42-94f0-4b41-b0e4-f91e65400978
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 4-[(3S,8R)-1,5-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxabicyclo[3.2.1]octan-8-yl]butan-2-one
• SMILES (Canonical): CC(=O)CCC1C2(CC(CC1(OC2)C)OC3C(C(C(C(O3)CO)O)O)O)C
• SMILES (Isomeric): CC(=O)CC[C@@H]1C2(C[C@@H](CC1(OC2)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C
• InChI: InChI=1S/C19H32O8/c1-10(21)4-5-13-18(2)6-11(7-19(13,3)25-9-18)26-17-16(24)15(23)14(22)12(8-20)27-17/h11-17,20,22-24H,4-9H2,1-3H3/t11-,12+,13+,14+,15-,16+,17+,18?,19?/m0/s1
• InChI Key: FUGMJWOONJABQQ-UBHNRPOQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₂O₈
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.20971797 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 325686-49-5
• AKOS032948478

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6695	66.95%
Caco-2	-	0.7691	76.91%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7411	74.11%
OATP2B1 inhibitior	-	0.7191	71.91%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7879	78.79%
P-glycoprotein inhibitior	-	0.7896	78.96%
P-glycoprotein substrate	-	0.8755	87.55%
CYP3A4 substrate	+	0.6131	61.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9544	95.44%
CYP2C9 inhibition	-	0.8746	87.46%
CYP2C19 inhibition	-	0.8677	86.77%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.9124	91.24%
CYP2C8 inhibition	-	0.8294	82.94%
CYP inhibitory promiscuity	-	0.9614	96.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6740	67.40%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9608	96.08%
Skin irritation	-	0.7145	71.45%
Skin corrosion	-	0.9511	95.11%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6971	69.71%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7143	71.43%
skin sensitisation	-	0.9363	93.63%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6936	69.36%
Acute Oral Toxicity (c)	I	0.5752	57.52%
Estrogen receptor binding	-	0.4849	48.49%
Androgen receptor binding	+	0.5396	53.96%
Thyroid receptor binding	+	0.6063	60.63%
Glucocorticoid receptor binding	-	0.4782	47.82%
Aromatase binding	+	0.7025	70.25%
PPAR gamma	-	0.5132	51.32%
Honey bee toxicity	-	0.7659	76.59%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7155	71.55%
Fish aquatic toxicity	+	0.8714	87.14%

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	98.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.70%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.42%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.49%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.31%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	91.17%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.91%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	89.89%	92.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.98%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.56%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.89%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.72%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.36%	96.38%
CHEMBL2581	P07339	Cathepsin D	84.68%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	84.15%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.93%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.51%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.01%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.16%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.24%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.61%	96.77%
CHEMBL226	P30542	Adenosine A1 receptor	80.58%	95.93%

Plants that contains it

• Aucklandia costus

Cross-Links

• PubChem: 102004450
• NPASS: NPC298650