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

Details

• Internal ID: 426c2aa7-7673-4d27-991d-b69777602110
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7S,7aS)-4-[[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-6,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C2C(CC(C2(C)O)O)C(=CO1)COC3C(C(C(C(O3)CO)O)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1[C@H]2[C@H](C[C@@H]([C@@]2(C)O)O)C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H38O13/c1-6-11(2)22(31)38-23-18-15(7-17(29)25(18,5)32)14(9-33-23)10-34-24-21(36-13(4)28)20(35-12(3)27)19(30)16(8-26)37-24/h9,11,15-21,23-24,26,29-30,32H,6-8,10H2,1-5H3/t11-,15-,16-,17+,18-,19-,20+,21-,23+,24-,25-/m1/s1
• InChI Key: LDDUHYKAAYRTBL-ZJWNIBOISA-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: -0.40
• 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	+	0.8075	80.75%
Caco-2	-	0.8150	81.50%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6585	65.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8096	80.96%
OATP1B3 inhibitior	+	0.9341	93.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5590	55.90%
P-glycoprotein inhibitior	+	0.6093	60.93%
P-glycoprotein substrate	-	0.5913	59.13%
CYP3A4 substrate	+	0.6712	67.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.7599	75.99%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.9035	90.35%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.9123	91.23%
CYP2C8 inhibition	+	0.4451	44.51%
CYP inhibitory promiscuity	-	0.9076	90.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6118	61.18%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9368	93.68%
Skin irritation	-	0.5673	56.73%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5365	53.65%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5181	51.81%
skin sensitisation	-	0.8983	89.83%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6837	68.37%
Acute Oral Toxicity (c)	III	0.7073	70.73%
Estrogen receptor binding	+	0.6994	69.94%
Androgen receptor binding	+	0.6743	67.43%
Thyroid receptor binding	-	0.6092	60.92%
Glucocorticoid receptor binding	+	0.6507	65.07%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6035	60.35%
Honey bee toxicity	-	0.7379	73.79%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9495	94.95%

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	99.03%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	98.73%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.56%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.95%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.74%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.32%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.78%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.15%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.72%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.69%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	85.12%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	85.00%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.79%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.68%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.36%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.07%	86.92%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.19%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.90%	82.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.48%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.33%	95.56%

Plants that contains it

• Viburnum ayavacense

Cross-Links

• PubChem: 163010487
• LOTUS: LTS0255678
• wikiData: Q105150182