[(1S,4aS,7R,7aS)-4-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-7-methyl-6-oxo-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate

Details

• Internal ID: 3deb2d2f-58a5-4201-8419-0634c318f6a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,7R,7aS)-4-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-7-methyl-6-oxo-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC1C2C(CC1=O)C(=COC2OC(=O)CC(C)C)COC3C(C(C(C(O3)COC4C(C(CO4)(CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]2[C@H](CC1=O)C(=CO[C@H]2OC(=O)CC(C)C)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O
• InChI: InChI=1S/C26H40O14/c1-11(2)4-17(29)40-23-18-12(3)15(28)5-14(18)13(6-35-23)7-36-24-21(32)20(31)19(30)16(39-24)8-37-25-22(33)26(34,9-27)10-38-25/h6,11-12,14,16,18-25,27,30-34H,4-5,7-10H2,1-3H3/t12-,14+,16+,18+,19+,20-,21+,22-,23-,24+,25+,26+/m0/s1
• InChI Key: PQBSXAUWSRUXOK-OWAPQGEASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₄
• Molecular Weight: 576.60 g/mol
• Exact Mass: 576.24180595 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.06
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8087	80.87%
Caco-2	-	0.8706	87.06%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7987	79.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8221	82.21%
OATP1B3 inhibitior	+	0.9181	91.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5436	54.36%
P-glycoprotein inhibitior	-	0.4941	49.41%
P-glycoprotein substrate	+	0.5268	52.68%
CYP3A4 substrate	+	0.6768	67.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8788	87.88%
CYP3A4 inhibition	-	0.8413	84.13%
CYP2C9 inhibition	-	0.8705	87.05%
CYP2C19 inhibition	-	0.9125	91.25%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.9177	91.77%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.9331	93.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5758	57.58%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9391	93.91%
Skin irritation	-	0.6002	60.02%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	+	0.5746	57.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.8694	86.94%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.8816	88.16%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5077	50.77%
Acute Oral Toxicity (c)	I	0.5332	53.32%
Estrogen receptor binding	+	0.7456	74.56%
Androgen receptor binding	+	0.5979	59.79%
Thyroid receptor binding	-	0.5461	54.61%
Glucocorticoid receptor binding	+	0.5684	56.84%
Aromatase binding	+	0.5680	56.80%
PPAR gamma	+	0.5867	58.67%
Honey bee toxicity	-	0.7707	77.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9759	97.59%

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	97.90%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.85%	95.93%
CHEMBL2581	P07339	Cathepsin D	95.87%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.59%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.76%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.57%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.56%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.74%	86.92%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.93%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.26%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.10%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.81%	96.47%
CHEMBL4040	P28482	MAP kinase ERK2	84.22%	83.82%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.82%	82.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.78%	95.71%
CHEMBL5255	O00206	Toll-like receptor 4	83.70%	92.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.83%	94.80%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.80%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.58%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.85%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.39%	97.21%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.34%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.65%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.58%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.08%	99.17%

Plants that contains it

• Sambucus ebulus

Cross-Links

• PubChem: 21587053
• LOTUS: LTS0071614
• wikiData: Q105213149