[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9S,10R,13R,14R)-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: 076f39d2-05a3-482d-9134-05a4f5266ba1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9S,10R,13R,14R)-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC12CCCC(C1CCC34C2CCC(C3)C(C4)(CO)OC5C(C(C(C(O5)CO)O)O)O)(C)C(=O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)(C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H52O14/c1-29-7-3-8-30(2,28(42)45-26-24(40)22(38)20(36)16(11-33)43-26)18(29)6-9-31-10-15(4-5-19(29)31)32(13-31,14-35)46-27-25(41)23(39)21(37)17(12-34)44-27/h15-27,33-41H,3-14H2,1-2H3/t15-,16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31+,32+/m1/s1
• InChI Key: YWOHBGYYVUQKPV-NCNYVQIPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₂O₁₄
• Molecular Weight: 660.70 g/mol
• Exact Mass: 660.33570633 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5698	56.98%
Caco-2	-	0.8785	87.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7405	74.05%
OATP2B1 inhibitior	-	0.5832	58.32%
OATP1B1 inhibitior	+	0.8691	86.91%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9318	93.18%
P-glycoprotein inhibitior	+	0.6053	60.53%
P-glycoprotein substrate	-	0.7144	71.44%
CYP3A4 substrate	+	0.6978	69.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8518	85.18%
CYP3A4 inhibition	-	0.9669	96.69%
CYP2C9 inhibition	-	0.9068	90.68%
CYP2C19 inhibition	-	0.8515	85.15%
CYP2D6 inhibition	-	0.9563	95.63%
CYP1A2 inhibition	-	0.8862	88.62%
CYP2C8 inhibition	-	0.5645	56.45%
CYP inhibitory promiscuity	-	0.9614	96.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7142	71.42%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9221	92.21%
Skin irritation	-	0.7293	72.93%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7025	70.25%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8852	88.52%
skin sensitisation	-	0.9402	94.02%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8525	85.25%
Acute Oral Toxicity (c)	I	0.5064	50.64%
Estrogen receptor binding	+	0.6636	66.36%
Androgen receptor binding	+	0.6639	66.39%
Thyroid receptor binding	-	0.5574	55.74%
Glucocorticoid receptor binding	-	0.4881	48.81%
Aromatase binding	+	0.6330	63.30%
PPAR gamma	+	0.5729	57.29%
Honey bee toxicity	-	0.7554	75.54%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8671	86.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	97.00%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.78%	97.25%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.95%	96.21%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.76%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.44%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.54%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.77%	95.50%
CHEMBL237	P41145	Kappa opioid receptor	89.61%	98.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	87.56%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.53%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.30%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.88%	95.83%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.59%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	83.06%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.69%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.14%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.47%	83.82%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.10%	100.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.44%	83.57%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.44%	96.33%

Plants that contains it

• Eleutherococcus trifoliatus

Cross-Links

• PubChem: 10985203
• LOTUS: LTS0173001
• wikiData: Q105366986