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

Details

• Internal ID: ca2e6197-8e87-429a-b910-3c82fe3ff8ef
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7S,7aS)-6-acetyloxy-4-[[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CC(C2(C)O)OC(=O)C)C(=CO1)COC3C(C(C(C(O3)CO)O)O)OC(=O)C
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@@]2(C)O)OC(=O)C)C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C
• InChI: InChI=1S/C25H38O13/c1-11(2)6-18(29)38-23-19-15(7-17(25(19,5)32)35-12(3)27)14(9-33-23)10-34-24-22(36-13(4)28)21(31)20(30)16(8-26)37-24/h9,11,15-17,19-24,26,30-32H,6-8,10H2,1-5H3/t15-,16-,17+,19-,20-,21+,22-,23+,24-,25-/m1/s1
• InChI Key: BCTQMTZTWOPJFZ-JXGCLKDXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₁₃
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.23124126 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.48
• H-Bond Acceptor: 13
• H-Bond Donor: 4
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7143	71.43%
Caco-2	-	0.8218	82.18%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7950	79.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8024	80.24%
OATP1B3 inhibitior	+	0.8813	88.13%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5571	55.71%
P-glycoprotein inhibitior	+	0.6342	63.42%
P-glycoprotein substrate	-	0.6031	60.31%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.9031	90.31%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.8920	89.20%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.8934	89.34%
CYP2C8 inhibition	-	0.6281	62.81%
CYP inhibitory promiscuity	-	0.8804	88.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6217	62.17%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.6670	66.70%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5351	53.51%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5819	58.19%
skin sensitisation	-	0.8741	87.41%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6993	69.93%
Acute Oral Toxicity (c)	III	0.6659	66.59%
Estrogen receptor binding	+	0.7429	74.29%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	-	0.6079	60.79%
Glucocorticoid receptor binding	+	0.6329	63.29%
Aromatase binding	-	0.4901	49.01%
PPAR gamma	+	0.6483	64.83%
Honey bee toxicity	-	0.7407	74.07%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9652	96.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.64%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.30%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.76%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	91.91%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.27%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.13%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.08%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	86.81%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.78%	86.92%
CHEMBL340	P08684	Cytochrome P450 3A4	85.38%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.20%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.71%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.62%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.55%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.51%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.25%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.97%	96.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.04%	82.50%

Plants that contains it

• Viburnum tinus

Cross-Links

• PubChem: 101915807
• LOTUS: LTS0016013
• wikiData: Q104666915