[(1S,4aS,6S,7S,7aS)-7-(acetyloxymethyl)-6-hydroxy-4-[[(2R,3S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: aa1225ff-b42c-4ae7-beb5-8de47eda127c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7S,7aS)-7-(acetyloxymethyl)-6-hydroxy-4-[[(2R,3S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-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)O
• 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)O
• InChI: InChI=1S/C29H44O16/c1-11(2)5-19(33)44-27-20-15(6-17(32)16(20)10-39-13(4)31)14(8-40-27)9-41-29-26(24(37)22(35)18(7-30)43-29)45-28-25(38)23(36)21(34)12(3)42-28/h8,11-12,15-18,20-23,25-30,32,34-36,38H,5-7,9-10H2,1-4H3/t12-,15+,16-,17-,18+,20-,21-,22+,23+,25+,26+,27-,28-,29+/m0/s1
• InChI Key: ABESPQSQOFAXBQ-XDGLZBGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₆
• Molecular Weight: 648.60 g/mol
• Exact Mass: 648.26293531 g/mol
• Topological Polar Surface Area (TPSA): 237.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.13
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 11

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	-	0.8800	88.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7795	77.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7897	78.97%
OATP1B3 inhibitior	+	0.9121	91.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4618	46.18%
P-glycoprotein inhibitior	-	0.4429	44.29%
P-glycoprotein substrate	+	0.5893	58.93%
CYP3A4 substrate	+	0.6849	68.49%
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	+	0.5577	55.77%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7071	70.71%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9303	93.03%
Skin irritation	-	0.7329	73.29%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4215	42.15%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5962	59.62%
skin sensitisation	-	0.8668	86.68%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.4838	48.38%
Acute Oral Toxicity (c)	III	0.5718	57.18%
Estrogen receptor binding	+	0.7245	72.45%
Androgen receptor binding	+	0.6688	66.88%
Thyroid receptor binding	-	0.5908	59.08%
Glucocorticoid receptor binding	+	0.6126	61.26%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5761	57.61%
Honey bee toxicity	-	0.6902	69.02%
Biodegradation	-	0.7500	75.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.37%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	94.16%	95.93%
CHEMBL4040	P28482	MAP kinase ERK2	93.98%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.81%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.19%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.19%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.11%	97.21%
CHEMBL340	P08684	Cytochrome P450 3A4	88.82%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.54%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.95%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	87.38%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.94%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.95%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	83.08%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.45%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.46%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.57%	96.00%

Plants that contains it

• Sambucus ebulus

Cross-Links

• PubChem: 44557019
• LOTUS: LTS0059964
• wikiData: Q104908576