(2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(1R,2R,4aS,5S,8R,8aR)-5,8-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 3bb387af-7b73-4fae-83ec-27ebacd0a06c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(1R,2R,4aS,5S,8R,8aR)-5,8-dihydroxy-2-(2-hydroxypropan-2-yl)-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC12CCC(C(C1C(CCC2O)(C)O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)C(C)(C)O
• SMILES (Isomeric): C[C@]12CC[C@H]([C@H]([C@@H]1[C@](CC[C@@H]2O)(C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)C(C)(C)O
• InChI: InChI=1S/C27H48O14/c1-25(2,36)11-5-7-26(3)14(29)6-8-27(4,37)22(26)21(11)41-24-20(35)18(33)16(31)13(40-24)10-38-23-19(34)17(32)15(30)12(9-28)39-23/h11-24,28-37H,5-10H2,1-4H3/t11-,12-,13-,14+,15-,16-,17+,18+,19-,20-,21-,22+,23+,24+,26-,27-/m1/s1
• InChI Key: ZXPNGVZPETVHKU-JAMAABBFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₈O₁₄
• Molecular Weight: 596.70 g/mol
• Exact Mass: 596.30440620 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.30
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5618	56.18%
Caco-2	-	0.8592	85.92%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6860	68.60%
OATP2B1 inhibitior	-	0.7312	73.12%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.8281	82.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8371	83.71%
P-glycoprotein inhibitior	-	0.5214	52.14%
P-glycoprotein substrate	-	0.8133	81.33%
CYP3A4 substrate	+	0.6823	68.23%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8352	83.52%
CYP3A4 inhibition	-	0.9470	94.70%
CYP2C9 inhibition	-	0.9033	90.33%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9629	96.29%
CYP1A2 inhibition	-	0.9072	90.72%
CYP2C8 inhibition	-	0.6202	62.02%
CYP inhibitory promiscuity	-	0.9826	98.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6935	69.35%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9206	92.06%
Skin irritation	-	0.7470	74.70%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6446	64.46%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6157	61.57%
skin sensitisation	-	0.9301	93.01%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.8203	82.03%
Acute Oral Toxicity (c)	III	0.4179	41.79%
Estrogen receptor binding	+	0.6168	61.68%
Androgen receptor binding	+	0.5491	54.91%
Thyroid receptor binding	-	0.5307	53.07%
Glucocorticoid receptor binding	+	0.5654	56.54%
Aromatase binding	+	0.7301	73.01%
PPAR gamma	+	0.6160	61.60%
Honey bee toxicity	-	0.7705	77.05%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7561	75.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.95%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.84%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.53%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.09%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.08%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.52%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.75%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	88.03%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.85%	93.04%
CHEMBL1871	P10275	Androgen Receptor	87.68%	96.43%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.34%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.60%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.02%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.11%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.93%	96.21%
CHEMBL1977	P11473	Vitamin D receptor	82.61%	99.43%
CHEMBL2581	P07339	Cathepsin D	81.92%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.25%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.21%	97.14%
CHEMBL5028	O14672	ADAM10	80.78%	97.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.49%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.22%	92.50%

Plants that contains it

• Ageratina saltillensis
• Dictamnus dasycarpus
• Esenbeckia hartmanii
• Grewia villosa
• Salta triflora
• Salvia polystachya
• Trifolium montanum

Cross-Links

• PubChem: 21592257
• NPASS: NPC50185
• LOTUS: LTS0181867
• wikiData: Q105385679