methyl (2S,4aS,6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4a,5,6,10,10a-hexahydro-1H-benzo[f]isochromene-7-carboxylate

Details

• Internal ID: 5745c524-c94b-4af1-b0a4-ab0bca550aba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: methyl (2S,4aS,6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4,9-dioxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4a,5,6,10,10a-hexahydro-1H-benzo[f]isochromene-7-carboxylate
• SMILES (Canonical): CC12CC(OC(=O)C1CC(C3(C2CC(=O)C=C3C(=O)OC)C)OC4C(C(C(C(O4)CO)O)O)O)C5=COC=C5
• SMILES (Isomeric): C[C@@]12C[C@H](OC(=O)[C@H]1C[C@@H]([C@@]3([C@H]2CC(=O)C=C3C(=O)OC)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=COC=C5
• InChI: InChI=1S/C27H34O12/c1-26-9-16(12-4-5-36-11-12)37-24(34)14(26)8-19(39-25-22(32)21(31)20(30)17(10-28)38-25)27(2)15(23(33)35-3)6-13(29)7-18(26)27/h4-6,11,14,16-22,25,28,30-32H,7-10H2,1-3H3/t14-,16+,17-,18+,19+,20-,21+,22-,25+,26-,27+/m1/s1
• InChI Key: YMNCHYBBYDAUSZ-SLIRKQLYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₂
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.20502652 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 12
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8730	87.30%
Caco-2	-	0.8194	81.94%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7523	75.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3294	32.94%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7859	78.59%
P-glycoprotein inhibitior	+	0.6012	60.12%
P-glycoprotein substrate	-	0.5093	50.93%
CYP3A4 substrate	+	0.7075	70.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8823	88.23%
CYP3A4 inhibition	-	0.7553	75.53%
CYP2C9 inhibition	-	0.8758	87.58%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8894	88.94%
CYP2C8 inhibition	+	0.5802	58.02%
CYP inhibitory promiscuity	-	0.8037	80.37%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.6719	67.19%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8600	86.00%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.6302	63.02%
skin sensitisation	-	0.8961	89.61%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4495	44.95%
Acute Oral Toxicity (c)	I	0.7410	74.10%
Estrogen receptor binding	+	0.7932	79.32%
Androgen receptor binding	+	0.6854	68.54%
Thyroid receptor binding	+	0.5221	52.21%
Glucocorticoid receptor binding	+	0.7181	71.81%
Aromatase binding	+	0.5553	55.53%
PPAR gamma	+	0.6197	61.97%
Honey bee toxicity	-	0.7122	71.22%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9885	98.85%

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	99.12%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.08%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.33%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.00%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.28%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.39%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.38%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.33%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.73%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.15%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.37%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.93%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.85%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.66%	94.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.77%	86.92%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.56%	91.24%
CHEMBL1951	P21397	Monoamine oxidase A	80.21%	91.49%

Plants that contains it

• Hypericum papuanum
• Thalictrum microgynum
• Tinospora crispa

Cross-Links

• PubChem: 21636046
• NPASS: NPC273131
• LOTUS: LTS0210181
• wikiData: Q105249306