methyl (1S,4aS,8R,8aR)-8-hydroxy-8-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,8a-tetrahydro-1H-pyrano[3,4-c]pyran-4-carboxylate

Details

• Internal ID: 0c9cda04-4068-4de1-9367-4dbb1551dfb9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1S,4aS,8R,8aR)-8-hydroxy-8-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,8a-tetrahydro-1H-pyrano[3,4-c]pyran-4-carboxylate
• SMILES (Canonical): CC1(C2C(CCO1)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC)O
• SMILES (Isomeric): C[C@@]1([C@@H]2[C@H](CCO1)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)OC)O
• InChI: InChI=1S/C17H26O11/c1-17(23)10-7(3-4-26-17)8(14(22)24-2)6-25-15(10)28-16-13(21)12(20)11(19)9(5-18)27-16/h6-7,9-13,15-16,18-21,23H,3-5H2,1-2H3/t7-,9-,10-,11-,12+,13-,15+,16+,17-/m1/s1
• InChI Key: WHAPPFLYHSDHAN-AYDWLWLASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₁₁
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.14751164 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6785	67.85%
Caco-2	-	0.8353	83.53%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7556	75.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7723	77.23%
OATP1B3 inhibitior	+	0.9132	91.32%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7819	78.19%
BSEP inhibitior	-	0.8731	87.31%
P-glycoprotein inhibitior	-	0.8691	86.91%
P-glycoprotein substrate	-	0.7542	75.42%
CYP3A4 substrate	+	0.6730	67.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.9661	96.61%
CYP2C9 inhibition	-	0.9155	91.55%
CYP2C19 inhibition	-	0.8936	89.36%
CYP2D6 inhibition	-	0.9120	91.20%
CYP1A2 inhibition	-	0.8684	86.84%
CYP2C8 inhibition	-	0.5717	57.17%
CYP inhibitory promiscuity	-	0.8931	89.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7052	70.52%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9756	97.56%
Skin irritation	-	0.7440	74.40%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5819	58.19%
Human Ether-a-go-go-Related Gene inhibition	-	0.5502	55.02%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.8047	80.47%
skin sensitisation	-	0.8837	88.37%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.7204	72.04%
Acute Oral Toxicity (c)	III	0.5947	59.47%
Estrogen receptor binding	+	0.6487	64.87%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5285	52.85%
Glucocorticoid receptor binding	-	0.4936	49.36%
Aromatase binding	+	0.5267	52.67%
PPAR gamma	+	0.5501	55.01%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.5331	53.31%

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	98.43%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.01%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.53%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.88%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.22%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.12%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.78%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.28%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.80%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.35%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	83.30%	92.50%
CHEMBL5028	O14672	ADAM10	82.77%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.74%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.23%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.88%	95.83%
CHEMBL221	P23219	Cyclooxygenase-1	81.70%	90.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.18%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.38%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.02%	92.94%

Plants that contains it

• Lamium album

Cross-Links

• PubChem: 163026642
• LOTUS: LTS0243129
• wikiData: Q105305190