methyl (1R,4S,9S,11S)-4-hydroxy-9-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undec-5-ene-11-carboxylate

Details

• Internal ID: f16c6296-d048-4d5a-aea1-7c1543f2753d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1R,4S,9S,11S)-4-hydroxy-9-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undec-5-ene-11-carboxylate
• SMILES (Canonical): COC(=O)C1C2C=CC3(C2C(OC1OC3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC(=O)[C@@H]1[C@@H]2OC[C@@]3(C=CC1C3[C@@H](O2)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C17H24O11/c1-24-13(22)8-6-2-3-17(23)5-25-14(8)27-15(9(6)17)28-16-12(21)11(20)10(19)7(4-18)26-16/h2-3,6-12,14-16,18-21,23H,4-5H2,1H3/t6?,7-,8+,9?,10-,11+,12-,14+,15-,16+,17+/m0/s1
• InChI Key: YFEOPJWHUMIDGW-FFCBOREKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.16
• 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	-	0.5750	57.50%
Caco-2	-	0.9006	90.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5189	51.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8146	81.46%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9422	94.22%
P-glycoprotein inhibitior	-	0.8438	84.38%
P-glycoprotein substrate	-	0.6178	61.78%
CYP3A4 substrate	+	0.6607	66.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8779	87.79%
CYP3A4 inhibition	-	0.9403	94.03%
CYP2C9 inhibition	-	0.9509	95.09%
CYP2C19 inhibition	-	0.8584	85.84%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.9333	93.33%
CYP2C8 inhibition	-	0.7361	73.61%
CYP inhibitory promiscuity	-	0.9221	92.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6345	63.45%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9741	97.41%
Skin irritation	-	0.7975	79.75%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6407	64.07%
Micronuclear	-	0.7241	72.41%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8738	87.38%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4695	46.95%
Acute Oral Toxicity (c)	III	0.4694	46.94%
Estrogen receptor binding	+	0.5969	59.69%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5493	54.93%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.5217	52.17%
Honey bee toxicity	-	0.7233	72.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.7641	76.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.97%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.60%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	91.80%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.82%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.40%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.55%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.90%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.50%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.42%	91.24%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.56%	97.53%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.77%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.56%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.19%	95.56%
CHEMBL2581	P07339	Cathepsin D	80.79%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.59%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.38%	97.21%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.34%	98.75%

Plants that contains it

• Primula macrophylla

Cross-Links

• PubChem: 101118343
• LOTUS: LTS0254192
• wikiData: Q105347544