(1R,2R,5S,8S,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-12-ene-9-carboxylic acid

Details

• Internal ID: 05d374fe-ab51-4be5-9f41-a5619e384206
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (1R,2R,5S,8S,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-12-ene-9-carboxylic acid
• SMILES (Canonical): CC12C=CCC3(C1C(C45C3CCC(C4)(C(=C)C5)OC6C(C(C(C(O6)CO)O)O)O)C(=O)O)OC2=O
• SMILES (Isomeric): C[C@@]12C=CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C(=O)O)OC2=O
• InChI: InChI=1S/C25H32O10/c1-11-8-23-10-24(11,34-20-17(29)16(28)15(27)12(9-26)33-20)7-4-13(23)25-6-3-5-22(2,21(32)35-25)18(25)14(23)19(30)31/h3,5,12-18,20,26-29H,1,4,6-10H2,2H3,(H,30,31)/t12-,13-,14-,15-,16+,17-,18-,20+,22-,23+,24+,25-/m1/s1
• InChI Key: URLKVGACTZHFEX-FCYQBUEGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₀
• Molecular Weight: 492.50 g/mol
• Exact Mass: 492.19954721 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.12
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6077	60.77%
Caco-2	-	0.8370	83.70%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8410	84.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8494	84.94%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	-	0.9005	90.05%
P-glycoprotein inhibitior	-	0.6316	63.16%
P-glycoprotein substrate	-	0.7342	73.42%
CYP3A4 substrate	+	0.6839	68.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.9214	92.14%
CYP2C9 inhibition	-	0.8445	84.45%
CYP2C19 inhibition	-	0.8523	85.23%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.8698	86.98%
CYP2C8 inhibition	+	0.5258	52.58%
CYP inhibitory promiscuity	-	0.8961	89.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6133	61.33%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9525	95.25%
Skin irritation	-	0.6446	64.46%
Skin corrosion	-	0.9336	93.36%
Ames mutagenesis	-	0.6224	62.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6184	61.84%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6921	69.21%
skin sensitisation	-	0.8679	86.79%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5191	51.91%
Acute Oral Toxicity (c)	III	0.4667	46.67%
Estrogen receptor binding	+	0.7315	73.15%
Androgen receptor binding	+	0.6532	65.32%
Thyroid receptor binding	-	0.5231	52.31%
Glucocorticoid receptor binding	+	0.5877	58.77%
Aromatase binding	+	0.7528	75.28%
PPAR gamma	+	0.5749	57.49%
Honey bee toxicity	-	0.8801	88.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9488	94.88%

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	96.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.30%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.06%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.88%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.98%	96.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.95%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.89%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.78%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	88.12%	83.82%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.34%	95.83%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.79%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.52%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.62%	92.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.01%	97.28%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.65%	99.23%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.55%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.00%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.36%	94.75%

Plants that contains it

• Phaseolus coccineus

Cross-Links

• PubChem: 11730702
• LOTUS: LTS0235918
• wikiData: Q105277835