[(1S,4aS,6S,7S,7aS)-4-[[(2R,3S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-acetyloxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-oxooxan-2-yl]oxymethyl]-7-(acetyloxymethyl)-6-hydroxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 7304cbd0-db7c-4378-8188-aa545cba8798
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7S,7aS)-4-[[(2R,3S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-acetyloxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-oxooxan-2-yl]oxymethyl]-7-(acetyloxymethyl)-6-hydroxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2=O)O)CO)OCC3=COC(C4C3CC(C4COC(=O)C)O)OC(=O)CC(C)C)O)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H](O[C@@H]([C@H](C2=O)O)CO)OCC3=CO[C@H]([C@H]4[C@@H]3C[C@@H]([C@@H]4COC(=O)C)O)OC(=O)CC(C)C)O)O)OC(=O)C
• InChI: InChI=1S/C31H46O17/c1-12(2)6-21(36)47-29-22-17(7-19(35)18(22)11-41-14(4)33)16(9-42-29)10-43-31-28(24(38)23(37)20(8-32)46-31)48-30-26(40)25(39)27(13(3)44-30)45-15(5)34/h9,12-13,17-20,22-23,25-32,35,37,39-40H,6-8,10-11H2,1-5H3/t13-,17+,18-,19-,20+,22-,23+,25-,26+,27-,28+,29-,30-,31+/m0/s1
• InChI Key: QDZCBAZYWGIRFP-VMIHXZBSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₁₇
• Molecular Weight: 690.70 g/mol
• Exact Mass: 690.27349999 g/mol
• Topological Polar Surface Area (TPSA): 243.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.56
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8572	85.72%
Caco-2	-	0.8711	87.11%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7795	77.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7855	78.55%
OATP1B3 inhibitior	+	0.9121	91.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6742	67.42%
P-glycoprotein inhibitior	+	0.6639	66.39%
P-glycoprotein substrate	+	0.6087	60.87%
CYP3A4 substrate	+	0.6965	69.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.8715	87.15%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.8839	88.39%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8672	86.72%
CYP2C8 inhibition	+	0.5640	56.40%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7071	70.71%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9234	92.34%
Skin irritation	-	0.7329	73.29%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3967	39.67%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5712	57.12%
skin sensitisation	-	0.8668	86.68%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5214	52.14%
Acute Oral Toxicity (c)	III	0.5718	57.18%
Estrogen receptor binding	+	0.7618	76.18%
Androgen receptor binding	+	0.6903	69.03%
Thyroid receptor binding	-	0.5541	55.41%
Glucocorticoid receptor binding	+	0.6936	69.36%
Aromatase binding	+	0.5514	55.14%
PPAR gamma	+	0.6600	66.00%
Honey bee toxicity	-	0.6806	68.06%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9668	96.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.58%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.31%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.16%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	95.82%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.33%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.23%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.77%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.11%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.70%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.19%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.95%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	86.25%	92.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.91%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.77%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.34%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.92%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.23%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.54%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.83%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.19%	95.83%

Plants that contains it

• Sambucus ebulus

Cross-Links

• PubChem: 44556951
• LOTUS: LTS0258544
• wikiData: Q105219056