[(1R,4S,4aS,5S,6S,8aR)-4,5-dihydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl] (2R)-2-hydroxy-3-methylbutanoate

Details

• Internal ID: b9784d77-9d3e-4509-95d6-b1c0ad5aed0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1R,4S,4aS,5S,6S,8aR)-4,5-dihydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl] (2R)-2-hydroxy-3-methylbutanoate
• InChI: InChI=1S/C27H44O13/c1-12(2)17(29)24(35)40-16-7-9-27(36,11-38-25-21(33)20(32)19(31)15(10-28)39-25)22-18(30)14(6-8-26(16,22)4)13(3)23(34)37-5/h12,14-22,25,28-33,36H,3,6-11H2,1-2,4-5H3/t14-,15+,16+,17+,18-,19+,20-,21+,22+,25+,26-,27+/m0/s1
• InChI Key: IIVAJNCEGDSBTE-FROUBUNWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₁₃
• Molecular Weight: 576.60 g/mol
• Exact Mass: 576.27819145 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.62
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7104	71.04%
Caco-2	-	0.8360	83.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8080	80.80%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.8701	87.01%
OATP1B3 inhibitior	+	0.8142	81.42%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8330	83.30%
P-glycoprotein inhibitior	-	0.4447	44.47%
P-glycoprotein substrate	-	0.6340	63.40%
CYP3A4 substrate	+	0.7024	70.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8916	89.16%
CYP3A4 inhibition	-	0.7259	72.59%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	-	0.7931	79.31%
CYP2D6 inhibition	-	0.9409	94.09%
CYP1A2 inhibition	-	0.8207	82.07%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9695	96.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7261	72.61%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9327	93.27%
Skin irritation	-	0.6381	63.81%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6438	64.38%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6707	67.07%
skin sensitisation	-	0.8738	87.38%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6775	67.75%
Acute Oral Toxicity (c)	III	0.7017	70.17%
Estrogen receptor binding	+	0.7298	72.98%
Androgen receptor binding	+	0.6626	66.26%
Thyroid receptor binding	-	0.5550	55.50%
Glucocorticoid receptor binding	+	0.5723	57.23%
Aromatase binding	+	0.6169	61.69%
PPAR gamma	+	0.6582	65.82%
Honey bee toxicity	-	0.7171	71.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9620	96.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.72%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.75%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.20%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	92.64%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.99%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.39%	95.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.73%	82.50%
CHEMBL2581	P07339	Cathepsin D	87.81%	98.95%
CHEMBL5028	O14672	ADAM10	87.78%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.55%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.48%	96.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.32%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.20%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.78%	94.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.69%	85.14%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.61%	97.47%
CHEMBL5255	O00206	Toll-like receptor 4	86.38%	92.50%
CHEMBL299	P17252	Protein kinase C alpha	85.84%	98.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.04%	89.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.42%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.36%	97.25%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	84.32%	95.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.20%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	84.10%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.10%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.89%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.77%	95.83%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.29%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.27%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.92%	96.21%
CHEMBL268	P43235	Cathepsin K	82.90%	96.85%
CHEMBL221	P23219	Cyclooxygenase-1	82.31%	90.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.41%	92.86%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.01%	96.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.00%	94.00%

Plants that contains it

• Ixeris repens

Cross-Links

• PubChem: 163024564
• LOTUS: LTS0207677
• wikiData: Q105113775