[(2R,3S,4S,5R,6R)-6-[[(3S,3aS,9aS,9bS)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: 2308199c-c505-4c8a-9016-bdf59bdd531c
• 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,9aS,9bS)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1C2CCC(=C3C(C2OC1=O)C(=CC3=O)COC4C(C(C(C(O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CCC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=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
• InChI: InChI=1S/C29H34O11/c1-13-3-8-18-14(2)28(36)40-27(18)23-16(10-19(31)22(13)23)11-38-29-26(35)25(34)24(33)20(39-29)12-37-21(32)9-15-4-6-17(30)7-5-15/h4-7,10,14,18,20,23-27,29-30,33-35H,3,8-9,11-12H2,1-2H3/t14-,18-,20+,23-,24+,25-,26+,27-,29+/m0/s1
• InChI Key: GAMSURTVDXDTRP-CUJUGGJGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₁
• Molecular Weight: 558.60 g/mol
• Exact Mass: 558.21011190 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8428	84.28%
Caco-2	-	0.8629	86.29%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8294	82.94%
OATP2B1 inhibitior	-	0.8648	86.48%
OATP1B1 inhibitior	+	0.8499	84.99%
OATP1B3 inhibitior	+	0.9061	90.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6714	67.14%
P-glycoprotein inhibitior	+	0.6016	60.16%
P-glycoprotein substrate	-	0.5277	52.77%
CYP3A4 substrate	+	0.6873	68.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	-	0.7624	76.24%
CYP2C9 inhibition	-	0.7606	76.06%
CYP2C19 inhibition	-	0.7084	70.84%
CYP2D6 inhibition	-	0.8517	85.17%
CYP1A2 inhibition	-	0.6352	63.52%
CYP2C8 inhibition	+	0.6626	66.26%
CYP inhibitory promiscuity	-	0.7133	71.33%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5570	55.70%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.7075	70.75%
Skin corrosion	-	0.9322	93.22%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6226	62.26%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8659	86.59%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8560	85.60%
Acute Oral Toxicity (c)	III	0.4361	43.61%
Estrogen receptor binding	+	0.7794	77.94%
Androgen receptor binding	+	0.7015	70.15%
Thyroid receptor binding	-	0.5957	59.57%
Glucocorticoid receptor binding	+	0.6711	67.11%
Aromatase binding	+	0.5902	59.02%
PPAR gamma	+	0.6175	61.75%
Honey bee toxicity	-	0.7973	79.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9932	99.32%

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	95.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.24%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.56%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.27%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.26%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.58%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.32%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.34%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.86%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	87.06%	83.82%
CHEMBL5255	O00206	Toll-like receptor 4	86.03%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.41%	86.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.38%	85.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.31%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.58%	90.08%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.45%	94.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.44%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.41%	96.61%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.63%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.51%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.46%	97.33%

Plants that contains it

• Crepidiastrum lanceolatum

Cross-Links

• PubChem: 21580546
• LOTUS: LTS0010631
• wikiData: Q105005479