[(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4a,5,6,6a,7,8,9,10,10a-decahydro-1H-benzo[f]isochromen-10-yl] acetate

Details

• Internal ID: e0d14299-581f-4e79-8b06-ab11c60ac845
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: [(2S,4aR,6aS,7R,9S,10R,10aR,10bS)-2-(furan-3-yl)-9-hydroxy-10b-methyl-4-oxo-7-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4a,5,6,6a,7,8,9,10,10a-decahydro-1H-benzo[f]isochromen-10-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(CC(C2C1C3(CC(OC(=O)C3CC2)C4=COC=C4)C)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H](C[C@H]([C@@H]2[C@@H]1[C@@]3(C[C@H](OC(=O)[C@@H]3CC2)C4=COC=C4)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C26H36O12/c1-11(28)35-23-15(29)7-16(37-25-22(32)21(31)20(30)18(9-27)38-25)13-3-4-14-24(33)36-17(12-5-6-34-10-12)8-26(14,2)19(13)23/h5-6,10,13-23,25,27,29-32H,3-4,7-9H2,1-2H3/t13-,14+,15+,16-,17+,18+,19+,20-,21+,22-,23+,25-,26-/m1/s1
• InChI Key: WAJJNHUEVQGAOS-QDMZWKJISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₂
• Molecular Weight: 540.60 g/mol
• Exact Mass: 540.22067658 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7535	75.35%
Caco-2	-	0.8758	87.58%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8232	82.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7373	73.73%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.8037	80.37%
BSEP inhibitior	-	0.6301	63.01%
P-glycoprotein inhibitior	-	0.5988	59.88%
P-glycoprotein substrate	-	0.6206	62.06%
CYP3A4 substrate	+	0.7145	71.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.6465	64.65%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.9274	92.74%
CYP2D6 inhibition	-	0.9489	94.89%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.4806	48.06%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6460	64.60%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9570	95.70%
Skin irritation	-	0.6702	67.02%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7472	74.72%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5764	57.64%
skin sensitisation	-	0.9401	94.01%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5779	57.79%
Acute Oral Toxicity (c)	I	0.6506	65.06%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	+	0.6435	64.35%
Thyroid receptor binding	-	0.5899	58.99%
Glucocorticoid receptor binding	+	0.5958	59.58%
Aromatase binding	+	0.5500	55.00%
PPAR gamma	+	0.5879	58.79%
Honey bee toxicity	-	0.7070	70.70%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9638	96.38%

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	98.69%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.15%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.12%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.22%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.82%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.45%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.32%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.24%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.02%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.97%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	85.71%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.99%	91.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.53%	96.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.56%	97.79%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.93%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.79%	95.83%
CHEMBL2581	P07339	Cathepsin D	81.56%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.27%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.24%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	80.12%	94.73%

Plants that contains it

• Tinospora sinensis

Cross-Links

• PubChem: 163039263
• LOTUS: LTS0187197
• wikiData: Q105300263