(2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(1S,2R,4aS,5S,8aR)-5-hydroxy-4a-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-8-methylidene-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: cddfd304-f12e-4c37-887f-3bdb7b943bf0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(1S,2R,4aS,5S,8aR)-5-hydroxy-4a-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-8-methylidene-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): CC(C)(C1CCC2(C(CCC(=C)C2C1OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)O)CO)O
• SMILES (Isomeric): CC(C)([C@@H]1CC[C@@]2([C@H](CCC(=C)[C@H]2[C@@H]1O[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)O)CO)O
• InChI: InChI=1S/C27H46O14/c1-11-4-5-15(30)27(10-29)7-6-12(26(2,3)37)23(16(11)27)41-25-22(36)20(34)18(32)14(40-25)9-38-24-21(35)19(33)17(31)13(8-28)39-24/h12-25,28-37H,1,4-10H2,2-3H3/t12-,13-,14-,15+,16+,17-,18-,19+,20+,21-,22-,23-,24+,25+,27+/m1/s1
• InChI Key: MUHQVUVBSBAZQQ-QMAQORJASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₆O₁₄
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.28875614 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.52
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5528	55.28%
Caco-2	-	0.8792	87.92%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7427	74.27%
OATP2B1 inhibitior	-	0.7312	73.12%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.8437	84.37%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6819	68.19%
BSEP inhibitior	-	0.8708	87.08%
P-glycoprotein inhibitior	-	0.5339	53.39%
P-glycoprotein substrate	-	0.7585	75.85%
CYP3A4 substrate	+	0.6594	65.94%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9509	95.09%
CYP2C9 inhibition	-	0.8800	88.00%
CYP2C19 inhibition	-	0.8523	85.23%
CYP2D6 inhibition	-	0.9126	91.26%
CYP1A2 inhibition	-	0.8576	85.76%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9542	95.42%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7018	70.18%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9319	93.19%
Skin irritation	-	0.6887	68.87%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.7123	71.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.7147	71.47%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7028	70.28%
skin sensitisation	-	0.8462	84.62%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7275	72.75%
Acute Oral Toxicity (c)	III	0.5904	59.04%
Estrogen receptor binding	+	0.6673	66.73%
Androgen receptor binding	+	0.6035	60.35%
Thyroid receptor binding	-	0.5122	51.22%
Glucocorticoid receptor binding	+	0.5493	54.93%
Aromatase binding	+	0.6940	69.40%
PPAR gamma	+	0.6386	63.86%
Honey bee toxicity	-	0.7532	75.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9089	90.89%

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	98.81%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.43%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.66%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.65%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.82%	95.89%
CHEMBL1977	P11473	Vitamin D receptor	87.70%	99.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.26%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	86.66%	95.93%
CHEMBL2581	P07339	Cathepsin D	86.33%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.79%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.68%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.51%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.89%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.13%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.85%	96.95%
CHEMBL1871	P10275	Androgen Receptor	81.55%	96.43%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.17%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.74%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.42%	94.73%

Plants that contains it

• Dictamnus dasycarpus

Cross-Links

• PubChem: 162888034
• LOTUS: LTS0207170
• wikiData: Q105172369