[(2R,3R,4S,5S,6R)-2-[[(3S,3aR,4S,9aR,9bR)-4-hydroxy-3,6-dimethyl-2-oxo-3a,4,5,7,9a,9b-hexahydro-3H-azuleno[8,7-b]furan-9-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: b4e43ba1-e2f2-4ef9-aff5-dd53a9b8940f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[[(3S,3aR,4S,9aR,9bR)-4-hydroxy-3,6-dimethyl-2-oxo-3a,4,5,7,9a,9b-hexahydro-3H-azuleno[8,7-b]furan-9-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1C2C(CC(=C3CC=C(C3C2OC1=O)COC4C(C(C(C(O4)CO)O)O)OC(=O)CC5=CC=C(C=C5)O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C3CC=C([C@@H]3[C@H]2OC1=O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)OC(=O)CC5=CC=C(C=C5)O)C)O
• InChI: InChI=1S/C29H36O11/c1-13-9-19(32)22-14(2)28(36)40-26(22)23-16(5-8-18(13)23)12-37-29-27(25(35)24(34)20(11-30)38-29)39-21(33)10-15-3-6-17(31)7-4-15/h3-7,14,19-20,22-27,29-32,34-35H,8-12H2,1-2H3/t14-,19-,20+,22+,23-,24+,25-,26-,27+,29+/m0/s1
• InChI Key: YFKNCWOCBRAOMI-LBYGCBGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₁
• Molecular Weight: 560.60 g/mol
• Exact Mass: 560.22576196 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8762	87.62%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7392	73.92%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.7986	79.86%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7080	70.80%
P-glycoprotein inhibitior	-	0.4395	43.95%
P-glycoprotein substrate	+	0.5409	54.09%
CYP3A4 substrate	+	0.6853	68.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.5555	55.55%
CYP2C9 inhibition	-	0.8574	85.74%
CYP2C19 inhibition	-	0.8108	81.08%
CYP2D6 inhibition	-	0.8889	88.89%
CYP1A2 inhibition	-	0.7811	78.11%
CYP2C8 inhibition	+	0.6154	61.54%
CYP inhibitory promiscuity	-	0.8701	87.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6041	60.41%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9388	93.88%
Skin irritation	-	0.7087	70.87%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4410	44.10%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5109	51.09%
skin sensitisation	-	0.8602	86.02%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5242	52.42%
Acute Oral Toxicity (c)	III	0.3782	37.82%
Estrogen receptor binding	+	0.7170	71.70%
Androgen receptor binding	+	0.7157	71.57%
Thyroid receptor binding	-	0.5152	51.52%
Glucocorticoid receptor binding	+	0.6096	60.96%
Aromatase binding	+	0.5765	57.65%
PPAR gamma	+	0.6481	64.81%
Honey bee toxicity	-	0.7052	70.52%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.9930	99.30%

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	96.84%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	93.15%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.99%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.58%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.98%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.63%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.05%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.80%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.37%	97.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.81%	85.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.99%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.56%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.99%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.81%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.61%	91.49%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.40%	90.93%
CHEMBL5255	O00206	Toll-like receptor 4	83.38%	92.50%

Plants that contains it

• Crepidiastrum keiskeanum

Cross-Links

• PubChem: 162925698
• LOTUS: LTS0198968
• wikiData: Q105347634