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

Details

• Internal ID: 7ac35fa5-2588-40ed-9963-b7de8883cc36
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(1S,4aS,6S,7S,7aS)-4-[[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-6-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(CC(C2CO)O)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@@H]2CO)O)C(=CO1)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C
• InChI: InChI=1S/C23H36O12/c1-10(2)4-17(28)35-22-18-13(5-15(27)14(18)6-24)12(8-31-22)9-32-23-21(33-11(3)26)20(30)19(29)16(7-25)34-23/h8,10,13-16,18-25,27,29-30H,4-7,9H2,1-3H3/t13-,14+,15+,16-,18+,19-,20+,21-,22+,23-/m1/s1
• InChI Key: VQANSJBWIGQANR-XQHAHDGLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₁₂
• Molecular Weight: 504.50 g/mol
• Exact Mass: 504.22067658 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.19
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6576	65.76%
Caco-2	-	0.8114	81.14%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7819	78.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7725	77.25%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6288	62.88%
P-glycoprotein inhibitior	-	0.5748	57.48%
P-glycoprotein substrate	-	0.6293	62.93%
CYP3A4 substrate	+	0.6374	63.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
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	-	0.6850	68.50%
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	-	0.9443	94.43%
Skin irritation	-	0.7436	74.36%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4494	44.94%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6143	61.43%
skin sensitisation	-	0.8796	87.96%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7149	71.49%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.6261	62.61%
Androgen receptor binding	+	0.6820	68.20%
Thyroid receptor binding	-	0.6553	65.53%
Glucocorticoid receptor binding	-	0.4670	46.70%
Aromatase binding	-	0.5745	57.45%
PPAR gamma	-	0.5121	51.21%
Honey bee toxicity	-	0.7485	74.85%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.86%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.34%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.26%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.61%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.72%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	89.33%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.14%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.66%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.73%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.40%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.13%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.75%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	83.97%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	83.31%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.55%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.59%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.10%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.78%	82.50%

Plants that contains it

• Phyllosma capensis
• Proustia ilicifolia
• Viburnum lantana
• Viburnum prunifolium

Cross-Links

• PubChem: 14109595
• NPASS: NPC24038
• LOTUS: LTS0141289
• wikiData: Q105291146