[(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]-6-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 5d1e7787-85e7-41bc-a996-148a67b5a53d
• 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]-6-hydroxy-7-(hydroxymethyl)-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(C4CO)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]4CO)O)OC(=O)CC(C)C)O)O)OC(=O)C
• InChI: InChI=1S/C29H44O16/c1-11(2)5-19(34)44-27-20-15(6-17(33)16(20)7-30)14(9-39-27)10-40-29-26(22(36)21(35)18(8-31)43-29)45-28-24(38)23(37)25(12(3)41-28)42-13(4)32/h9,11-12,15-18,20-21,23-31,33,35,37-38H,5-8,10H2,1-4H3/t12-,15+,16-,17-,18+,20-,21+,23-,24+,25-,26+,27-,28-,29+/m0/s1
• InChI Key: HXIVYBYRGASIGM-RBBRWFNCSA-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: -1.20
• 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	+	0.6576	65.76%
Caco-2	-	0.8757	87.57%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7819	78.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7843	78.43%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5657	56.57%
P-glycoprotein inhibitior	+	0.5718	57.18%
P-glycoprotein substrate	+	0.5908	59.08%
CYP3A4 substrate	+	0.6844	68.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.8613	86.13%
CYP2C9 inhibition	-	0.8864	88.64%
CYP2C19 inhibition	-	0.8697	86.97%
CYP2D6 inhibition	-	0.9083	90.83%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.5119	51.19%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6663	66.63%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9330	93.30%
Skin irritation	-	0.7436	74.36%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3689	36.89%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5712	57.12%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4500	45.00%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.7569	75.69%
Androgen receptor binding	+	0.6963	69.63%
Thyroid receptor binding	-	0.5910	59.10%
Glucocorticoid receptor binding	+	0.6034	60.34%
Aromatase binding	+	0.5629	56.29%
PPAR gamma	+	0.6148	61.48%
Honey bee toxicity	-	0.6725	67.25%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9451	94.51%

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	97.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.88%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.88%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.57%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.17%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	92.88%	95.93%
CHEMBL4040	P28482	MAP kinase ERK2	92.31%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.95%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.47%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	86.70%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.62%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	85.57%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.47%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.67%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.79%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.77%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	81.34%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.48%	100.00%

Plants that contains it

• Sambucus ebulus

Cross-Links

• PubChem: 44557020
• LOTUS: LTS0261109
• wikiData: Q105035025