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

Details

• Internal ID: eb4c9f79-8664-4a76-b8e6-06e025dd9300
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1R,4aR,5S,6R,8aS)-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-4-[[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-1-yl] 2-hydroxy-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(=O)OC1CCC(C2C1(CCC(C2O)C(=C)C(=O)OC)C)COC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): CC(C)C(C(=O)O[C@@H]1CCC([C@@H]2[C@@]1(CC[C@@H]([C@@H]2O)C(=C)C(=O)OC)C)CO[C@H]3C([C@H]([C@@H]([C@@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C27H44O12/c1-12(2)19(29)25(35)39-17-7-6-14(11-37-26-23(33)22(32)21(31)16(10-28)38-26)18-20(30)15(8-9-27(17,18)4)13(3)24(34)36-5/h12,14-23,26,28-33H,3,6-11H2,1-2,4-5H3/t14?,15-,16+,17-,18+,19?,20+,21-,22+,23?,26-,27-/m1/s1
• InChI Key: WZQRTEWYMMHGLI-YMMSZFTFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₁₂
• Molecular Weight: 560.60 g/mol
• Exact Mass: 560.28327683 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6584	65.84%
Caco-2	-	0.8408	84.08%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8352	83.52%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	-	0.2210	22.10%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.7922	79.22%
P-glycoprotein inhibitior	-	0.4654	46.54%
P-glycoprotein substrate	-	0.5864	58.64%
CYP3A4 substrate	+	0.6901	69.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8872	88.72%
CYP3A4 inhibition	-	0.8283	82.83%
CYP2C9 inhibition	-	0.7946	79.46%
CYP2C19 inhibition	-	0.7832	78.32%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	-	0.7945	79.45%
CYP2C8 inhibition	-	0.6005	60.05%
CYP inhibitory promiscuity	-	0.9491	94.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7236	72.36%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9376	93.76%
Skin irritation	-	0.6701	67.01%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6436	64.36%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6082	60.82%
skin sensitisation	-	0.8784	87.84%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6308	63.08%
Acute Oral Toxicity (c)	III	0.6969	69.69%
Estrogen receptor binding	+	0.7098	70.98%
Androgen receptor binding	+	0.6523	65.23%
Thyroid receptor binding	-	0.5837	58.37%
Glucocorticoid receptor binding	+	0.5781	57.81%
Aromatase binding	+	0.6271	62.71%
PPAR gamma	+	0.6400	64.00%
Honey bee toxicity	-	0.7207	72.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	99.66%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.22%	96.47%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.19%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.84%	95.71%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.06%	96.61%
CHEMBL268	P43235	Cathepsin K	90.43%	96.85%
CHEMBL5255	O00206	Toll-like receptor 4	90.28%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.79%	97.25%
CHEMBL5028	O14672	ADAM10	88.66%	97.50%
CHEMBL4072	P07858	Cathepsin B	88.22%	93.67%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.10%	96.38%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.92%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.88%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.81%	96.21%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.50%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.32%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.16%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.87%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.30%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.89%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.62%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.53%	97.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.68%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.34%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.30%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.27%	91.24%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.15%	82.50%
CHEMBL237	P41145	Kappa opioid receptor	84.14%	98.10%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.06%	95.83%
CHEMBL4073	P09237	Matrix metalloproteinase 7	82.78%	97.56%
CHEMBL4581	P52732	Kinesin-like protein 1	82.49%	93.18%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.75%	97.14%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.16%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.87%	95.36%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.29%	94.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.08%	97.50%

Plants that contains it

• Ixeris repens

Cross-Links

• PubChem: 101589327
• LOTUS: LTS0153537
• wikiData: Q105323402