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

Details

• Internal ID: 8ab3ac90-24af-4b7e-9d17-cc83e25841d0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7R,7aS)-6-acetyloxy-7-(acetyloxymethyl)-7-hydroxy-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CC(C2(COC(=O)C)O)OC(=O)C)C(=CO1)COC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@@]2(COC(=O)C)O)OC(=O)C)C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C25H38O14/c1-11(2)5-18(29)39-23-19-15(6-17(37-13(4)28)25(19,33)10-36-12(3)27)14(8-34-23)9-35-24-22(32)21(31)20(30)16(7-26)38-24/h8,11,15-17,19-24,26,30-33H,5-7,9-10H2,1-4H3/t15-,16-,17+,19-,20-,21+,22-,23+,24-,25-/m1/s1
• InChI Key: GXOLEBHJEQBYAG-JXGCLKDXSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₁₄
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.22615588 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.51
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7706	77.06%
Caco-2	-	0.8493	84.93%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8116	81.16%
OATP1B3 inhibitior	+	0.8821	88.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7703	77.03%
P-glycoprotein inhibitior	-	0.4382	43.82%
P-glycoprotein substrate	-	0.5540	55.40%
CYP3A4 substrate	+	0.6689	66.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.8821	88.21%
CYP2C9 inhibition	-	0.8761	87.61%
CYP2C19 inhibition	-	0.9170	91.70%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9185	91.85%
CYP2C8 inhibition	+	0.4856	48.56%
CYP inhibitory promiscuity	-	0.9525	95.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6499	64.99%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9287	92.87%
Skin irritation	-	0.6162	61.62%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4367	43.67%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7090	70.90%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5736	57.36%
Acute Oral Toxicity (c)	I	0.4619	46.19%
Estrogen receptor binding	+	0.7554	75.54%
Androgen receptor binding	+	0.6571	65.71%
Thyroid receptor binding	-	0.6367	63.67%
Glucocorticoid receptor binding	+	0.6307	63.07%
Aromatase binding	+	0.5351	53.51%
PPAR gamma	+	0.6375	63.75%
Honey bee toxicity	-	0.7220	72.20%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9711	97.11%

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	99.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.72%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.76%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.48%	95.93%
CHEMBL2581	P07339	Cathepsin D	92.46%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	91.32%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.50%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.89%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.08%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.97%	97.21%
CHEMBL2996	Q05655	Protein kinase C delta	86.84%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.41%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.48%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.27%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.15%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.91%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	84.30%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.40%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.33%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.30%	91.19%

Plants that contains it

• Artemisia pedemontana
• Benkara malabarica
• Calea cuneifolia
• Dracocephalum moldavica
• Eucalyptus rubida
• Eurya japonica
• Hemionitis lemmonii
• Juniperus formosana
• Mucuna urens
• Murdannia triquetra
• Ozothamnus ferrugineus
• Phlomis nissolii
• Piper marginatum
• Stephania merrillii
• Styrax japonicus
• Tanacetum balsamitoides
• Verbascum spinosum
• Viburnum furcatum
• Viburnum tinus

Cross-Links

• PubChem: 14414526
• NPASS: NPC94256
• LOTUS: LTS0249561
• wikiData: Q104394915