[(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,7,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: 093e57ca-937b-44bb-a6fa-76e65ac27cf4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,7,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1=C2CC=C(C2C3C(C(C1)OC4C(C(C(C(O4)CO)O)O)O)C(=C)C(=O)O3)COC5C(C(C(C(O5)COC(=O)CC6=CC=C(C=C6)O)O)O)O
• SMILES (Isomeric): CC1=C2CC=C([C@@H]2[C@@H]3[C@@H]([C@H](C1)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=C)C(=O)O3)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)CC6=CC=C(C=C6)O)O)O)O
• InChI: InChI=1S/C35H44O16/c1-14-9-20(48-35-31(44)28(41)26(39)21(11-36)49-35)24-15(2)33(45)51-32(24)25-17(5-8-19(14)25)12-47-34-30(43)29(42)27(40)22(50-34)13-46-23(38)10-16-3-6-18(37)7-4-16/h3-7,20-22,24-32,34-37,39-44H,2,8-13H2,1H3/t20-,21+,22+,24+,25-,26+,27+,28-,29-,30+,31+,32-,34+,35+/m0/s1
• InChI Key: NWAICQLPBNMFRL-CFLGGORVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₆
• Molecular Weight: 720.70 g/mol
• Exact Mass: 720.26293531 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -1.75
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8515	85.15%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7387	73.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.9413	94.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8993	89.93%
P-glycoprotein inhibitior	+	0.6640	66.40%
P-glycoprotein substrate	+	0.5246	52.46%
CYP3A4 substrate	+	0.7004	70.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8827	88.27%
CYP3A4 inhibition	-	0.7550	75.50%
CYP2C9 inhibition	-	0.8292	82.92%
CYP2C19 inhibition	-	0.7133	71.33%
CYP2D6 inhibition	-	0.8841	88.41%
CYP1A2 inhibition	-	0.7766	77.66%
CYP2C8 inhibition	+	0.7288	72.88%
CYP inhibitory promiscuity	-	0.7821	78.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6342	63.42%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9154	91.54%
Skin irritation	-	0.7389	73.89%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6997	69.97%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.6643	66.43%
skin sensitisation	-	0.8285	82.85%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6839	68.39%
Acute Oral Toxicity (c)	III	0.4535	45.35%
Estrogen receptor binding	+	0.8061	80.61%
Androgen receptor binding	+	0.6860	68.60%
Thyroid receptor binding	-	0.5198	51.98%
Glucocorticoid receptor binding	+	0.6613	66.13%
Aromatase binding	+	0.5814	58.14%
PPAR gamma	+	0.7282	72.82%
Honey bee toxicity	-	0.6848	68.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9970	99.70%

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	95.23%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.22%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.03%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.75%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.69%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	91.25%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.74%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.73%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.64%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.34%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.15%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.44%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.34%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.55%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.05%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	85.87%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.81%	97.36%
CHEMBL220	P22303	Acetylcholinesterase	83.54%	94.45%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.27%	97.33%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.20%	90.93%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.38%	93.65%

Plants that contains it

• Crepidiastrum lanceolatum

Cross-Links

• PubChem: 102465586
• LOTUS: LTS0171151
• wikiData: Q105186500