[(2R,3S,4S,5R,6R)-6-[[(3S,3aS,5R,9aR,9bS)-5-hydroxy-3,6-dimethyl-2-oxo-3a,4,5,7,9a,9b-hexahydro-3H-azuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: acf18079-fca5-423f-99a3-0fdc3170a16f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3S,3aS,5R,9aR,9bS)-5-hydroxy-3,6-dimethyl-2-oxo-3a,4,5,7,9a,9b-hexahydro-3H-azuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1C2CC(C(=C3CC=C(C3C2OC1=O)COC4C(C(C(C(O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@H](C(=C3CC=C([C@@H]3[C@H]2OC1=O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)C)O
• InChI: InChI=1S/C29H36O11/c1-13-18-8-5-16(23(18)27-19(10-20(13)31)14(2)28(36)40-27)11-38-29-26(35)25(34)24(33)21(39-29)12-37-22(32)9-15-3-6-17(30)7-4-15/h3-7,14,19-21,23-27,29-31,33-35H,8-12H2,1-2H3/t14-,19-,20+,21+,23-,24+,25-,26+,27-,29+/m0/s1
• InChI Key: RXSKLDPLNDXENS-MVDAHXLOSA-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: -0.50
• 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	+	0.8890	88.90%
Caco-2	-	0.8735	87.35%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7666	76.66%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8474	84.74%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6309	63.09%
P-glycoprotein inhibitior	-	0.4639	46.39%
P-glycoprotein substrate	+	0.5379	53.79%
CYP3A4 substrate	+	0.6943	69.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.7517	75.17%
CYP2C9 inhibition	-	0.8550	85.50%
CYP2C19 inhibition	-	0.7632	76.32%
CYP2D6 inhibition	-	0.8577	85.77%
CYP1A2 inhibition	-	0.7929	79.29%
CYP2C8 inhibition	+	0.6771	67.71%
CYP inhibitory promiscuity	-	0.8324	83.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6177	61.77%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9397	93.97%
Skin irritation	-	0.7378	73.78%
Skin corrosion	-	0.9406	94.06%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5758	57.58%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5321	53.21%
skin sensitisation	-	0.8295	82.95%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7113	71.13%
Acute Oral Toxicity (c)	III	0.3827	38.27%
Estrogen receptor binding	+	0.7350	73.50%
Androgen receptor binding	+	0.6685	66.85%
Thyroid receptor binding	-	0.5426	54.26%
Glucocorticoid receptor binding	+	0.6652	66.52%
Aromatase binding	+	0.5816	58.16%
PPAR gamma	+	0.5918	59.18%
Honey bee toxicity	-	0.7343	73.43%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	96.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.91%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.84%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	91.36%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.17%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.92%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.25%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.74%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.66%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.36%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.23%	90.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.44%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.46%	85.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.54%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.36%	92.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.25%	96.61%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.11%	90.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.98%	94.80%

Plants that contains it

• Crepidiastrum lanceolatum

Cross-Links

• PubChem: 21580543
• LOTUS: LTS0211108
• wikiData: Q105247275