methyl (1R,8S,9S,10R,12R)-9-[(2R)-2-(furan-3-yl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyethyl]-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.04,12]dodec-4-ene-10-carboxylate

Details

• Internal ID: 4602ef0e-ddab-4457-951d-5f8ba731cf5b
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: methyl (1R,8S,9S,10R,12R)-9-[(2R)-2-(furan-3-yl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyethyl]-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.04,12]dodec-4-ene-10-carboxylate
• SMILES (Canonical): CC1(C2CCC=C3C2(C(CC1C(=O)OC)OC3=O)C)CC(C4=COC=C4)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@]1([C@@H]2CCC=C3[C@@]2([C@@H](C[C@H]1C(=O)OC)OC3=O)C)C[C@H](C4=COC=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O
• InChI: InChI=1S/C33H46O16/c1-32(16(28(41)43-3)9-21-33(2)15(29(42)49-21)5-4-6-20(32)33)10-17(14-7-8-44-12-14)46-31-27(40)25(38)23(36)19(48-31)13-45-30-26(39)24(37)22(35)18(11-34)47-30/h5,7-8,12,16-27,30-31,34-40H,4,6,9-11,13H2,1-3H3/t16-,17+,18+,19+,20-,21+,22+,23+,24-,25-,26+,27+,30+,31+,32+,33-/m0/s1
• InChI Key: HBQVGXLPTJJJCH-FXVXIALZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₆O₁₆
• Molecular Weight: 698.70 g/mol
• Exact Mass: 698.27858538 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.18
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8102	81.02%
Caco-2	-	0.8837	88.37%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8267	82.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7841	78.41%
OATP1B3 inhibitior	+	0.8956	89.56%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	-	0.4798	47.98%
P-glycoprotein inhibitior	+	0.6904	69.04%
P-glycoprotein substrate	+	0.6249	62.49%
CYP3A4 substrate	+	0.7195	71.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8871	88.71%
CYP3A4 inhibition	-	0.8099	80.99%
CYP2C9 inhibition	-	0.8980	89.80%
CYP2C19 inhibition	-	0.8896	88.96%
CYP2D6 inhibition	-	0.9371	93.71%
CYP1A2 inhibition	-	0.8599	85.99%
CYP2C8 inhibition	+	0.6465	64.65%
CYP inhibitory promiscuity	-	0.9015	90.15%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4960	49.60%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9258	92.58%
Skin irritation	-	0.6073	60.73%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7983	79.83%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5423	54.23%
skin sensitisation	-	0.9160	91.60%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6556	65.56%
Acute Oral Toxicity (c)	I	0.5304	53.04%
Estrogen receptor binding	+	0.7983	79.83%
Androgen receptor binding	+	0.6932	69.32%
Thyroid receptor binding	-	0.5352	53.52%
Glucocorticoid receptor binding	+	0.6886	68.86%
Aromatase binding	+	0.6227	62.27%
PPAR gamma	+	0.6467	64.67%
Honey bee toxicity	-	0.7087	70.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9777	97.77%

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	98.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.57%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.91%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.41%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.85%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	90.97%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.57%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	89.98%	90.17%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.82%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.22%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.44%	92.50%
CHEMBL5028	O14672	ADAM10	85.64%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.80%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.95%	94.80%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.70%	95.83%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.60%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.61%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.43%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.39%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	80.81%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.62%	92.62%

Plants that contains it

• Thalictrum microgynum
• Tinospora crispa

Cross-Links

• PubChem: 21625634
• NPASS: NPC95135
• LOTUS: LTS0186822
• wikiData: Q105025443