[(2R,3S,4S,5R,6R)-6-[[(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]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: 57a5791e-7b3c-498a-962a-b788054f5b8b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(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]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1C2C(CC(=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]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)COC(=O)CC5=CC=C(C=C5)O)O)O)O)C)O
• InChI: InChI=1S/C29H36O11/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/h3-7,14,19-20,22-27,29-31,33-35H,8-12H2,1-2H3/t14-,19-,20+,22+,23-,24+,25-,26+,27-,29+/m0/s1
• InChI Key: VKVWKJOINFYMQJ-GOZBDGMGSA-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: -0.30
• 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	+	0.8989	89.89%
Caco-2	-	0.8830	88.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.8379	83.79%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6427	64.27%
P-glycoprotein inhibitior	-	0.4718	47.18%
P-glycoprotein substrate	-	0.5126	51.26%
CYP3A4 substrate	+	0.6893	68.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.5707	57.07%
CYP2C9 inhibition	-	0.8317	83.17%
CYP2C19 inhibition	-	0.7822	78.22%
CYP2D6 inhibition	-	0.8803	88.03%
CYP1A2 inhibition	-	0.7676	76.76%
CYP2C8 inhibition	+	0.6479	64.79%
CYP inhibitory promiscuity	-	0.8547	85.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9404	94.04%
Skin irritation	-	0.7084	70.84%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5814	58.14%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5523	55.23%
skin sensitisation	-	0.8468	84.68%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5528	55.28%
Acute Oral Toxicity (c)	I	0.4023	40.23%
Estrogen receptor binding	+	0.7477	74.77%
Androgen receptor binding	+	0.6693	66.93%
Thyroid receptor binding	-	0.5427	54.27%
Glucocorticoid receptor binding	+	0.6660	66.60%
Aromatase binding	+	0.5758	57.58%
PPAR gamma	+	0.5923	59.23%
Honey bee toxicity	-	0.7257	72.57%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.9962	99.62%

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	97.54%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.65%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.97%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.63%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.28%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.85%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.38%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.25%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.85%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.42%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.38%	97.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.24%	85.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.06%	90.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.54%	90.93%
CHEMBL5255	O00206	Toll-like receptor 4	81.47%	92.50%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.21%	93.65%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.17%	82.38%

Plants that contains it

• Crepidiastrum lanceolatum

Cross-Links

• PubChem: 101176808
• LOTUS: LTS0221025
• wikiData: Q104399039