(5S,6aS,7R,8R,10aS)-7,8-dimethyl-7-[2-(5-oxo-2H-furan-3-yl)ethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,6a,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-3-one

Details

• Internal ID: ea526108-eb26-46fe-b011-38840e943932
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (5S,6aS,7R,8R,10aS)-7,8-dimethyl-7-[2-(5-oxo-2H-furan-3-yl)ethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,6a,8,9,10-hexahydro-1H-benzo[d][2]benzofuran-3-one
• SMILES (Canonical): CC1CCC23COC(=O)C2=CC(CC3C1(C)CCC4=CC(=O)OC4)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]23COC(=O)C2=C[C@H](C[C@H]3[C@]1(C)CCC4=CC(=O)OC4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C26H36O10/c1-13-3-6-26-12-34-23(32)16(26)8-15(35-24-22(31)21(30)20(29)17(10-27)36-24)9-18(26)25(13,2)5-4-14-7-19(28)33-11-14/h7-8,13,15,17-18,20-22,24,27,29-31H,3-6,9-12H2,1-2H3/t13-,15-,17-,18+,20-,21+,22-,24-,25-,26-/m1/s1
• InChI Key: KNJRWXIFEPTPEB-NTXGUCJTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₀
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.23084734 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7624	76.24%
Caco-2	-	0.8324	83.24%
Blood Brain Barrier	-	0.5911	59.11%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8891	88.91%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.8468	84.68%
OATP1B3 inhibitior	+	0.8950	89.50%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5521	55.21%
BSEP inhibitior	+	0.5678	56.78%
P-glycoprotein inhibitior	-	0.4752	47.52%
P-glycoprotein substrate	-	0.5639	56.39%
CYP3A4 substrate	+	0.7079	70.79%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.9118	91.18%
CYP2C9 inhibition	-	0.9138	91.38%
CYP2C19 inhibition	-	0.9325	93.25%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.8798	87.98%
CYP2C8 inhibition	+	0.5801	58.01%
CYP inhibitory promiscuity	-	0.9165	91.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5325	53.25%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9462	94.62%
Skin irritation	-	0.5403	54.03%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	-	0.6324	63.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7205	72.05%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9273	92.73%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5687	56.87%
Acute Oral Toxicity (c)	III	0.5138	51.38%
Estrogen receptor binding	+	0.8153	81.53%
Androgen receptor binding	+	0.6932	69.32%
Thyroid receptor binding	-	0.6047	60.47%
Glucocorticoid receptor binding	+	0.6686	66.86%
Aromatase binding	+	0.7714	77.14%
PPAR gamma	+	0.6206	62.06%
Honey bee toxicity	-	0.6364	63.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9737	97.37%

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	99.07%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.05%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.61%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.57%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.40%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.97%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.38%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.26%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.67%	95.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.33%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.02%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.93%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.47%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.87%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.10%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.26%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.07%	93.04%

Plants that contains it

• Solidago gigantea

Cross-Links

• PubChem: 13994694
• LOTUS: LTS0089622
• wikiData: Q105143442