[(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-4-hydroxy-6-methyl-3-methylidene-2-oxo-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: dc7c32e0-925e-4611-b3aa-207d758f21e3
• 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)-4-hydroxy-6-methyl-3-methylidene-2-oxo-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)O)C(=C)C(=O)O3)COC4C(C(C(C(O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): CC1=C2CC=C([C@@H]2[C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C29H34O11/c1-13-9-19(31)22-14(2)28(36)40-27(22)23-16(5-8-18(13)23)11-38-29-26(35)25(34)24(33)20(39-29)12-37-21(32)10-15-3-6-17(30)7-4-15/h3-7,19-20,22-27,29-31,33-35H,2,8-12H2,1H3/t19-,20+,22+,23-,24+,25-,26+,27-,29+/m0/s1
• InChI Key: IUMVSFAJKAOULC-WVGLFDRFSA-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): 172.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.43
• 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	+	0.8965	89.65%
Caco-2	-	0.8855	88.55%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7331	73.31%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8368	83.68%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6835	68.35%
P-glycoprotein inhibitior	-	0.4545	45.45%
P-glycoprotein substrate	-	0.5198	51.98%
CYP3A4 substrate	+	0.6887	68.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8840	88.40%
CYP3A4 inhibition	-	0.6982	69.82%
CYP2C9 inhibition	-	0.8247	82.47%
CYP2C19 inhibition	-	0.7096	70.96%
CYP2D6 inhibition	-	0.8681	86.81%
CYP1A2 inhibition	-	0.7726	77.26%
CYP2C8 inhibition	+	0.6712	67.12%
CYP inhibitory promiscuity	-	0.8655	86.55%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6047	60.47%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9315	93.15%
Skin irritation	-	0.7206	72.06%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4161	41.61%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5809	58.09%
skin sensitisation	-	0.8170	81.70%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6078	60.78%
Acute Oral Toxicity (c)	III	0.4204	42.04%
Estrogen receptor binding	+	0.8082	80.82%
Androgen receptor binding	+	0.6860	68.60%
Thyroid receptor binding	-	0.5417	54.17%
Glucocorticoid receptor binding	+	0.6607	66.07%
Aromatase binding	+	0.6041	60.41%
PPAR gamma	+	0.6609	66.09%
Honey bee toxicity	-	0.7111	71.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.83%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.37%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.77%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.22%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.29%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.56%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.93%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.65%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.09%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.74%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.62%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.63%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.76%	95.89%
CHEMBL5957	P21589	5'-nucleotidase	81.66%	97.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.25%	95.64%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.11%	97.36%

Plants that contains it

• Crepidiastrum lanceolatum
• Lippia integrifolia
• Pellia epiphylla
• Porella swartziana

Cross-Links

• PubChem: 101176807
• LOTUS: LTS0167961
• wikiData: Q105246866