[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(E,5R)-5-hydroxy-7-methyl-3-methylidene-8-oxooct-6-enoxy]oxan-3-yl] acetate

Details

• Internal ID: c5ba8207-66f1-441f-9c0a-7d47f5a172b1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(E,5R)-5-hydroxy-7-methyl-3-methylidene-8-oxooct-6-enoxy]oxan-3-yl] acetate
• SMILES (Canonical): CC(=CC(CC(=C)CCOC1C(C(C(C(O1)CO)O)O)OC(=O)C)O)C=O
• SMILES (Isomeric): C/C(=C\[C@@H](CC(=C)CCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)OC(=O)C)O)/C=O
• InChI: InChI=1S/C18H28O9/c1-10(6-13(22)7-11(2)8-19)4-5-25-18-17(26-12(3)21)16(24)15(23)14(9-20)27-18/h7-8,13-18,20,22-24H,1,4-6,9H2,2-3H3/b11-7+/t13-,14-,15-,16+,17-,18-/m1/s1
• InChI Key: DCPPWJWOVYBRSD-BTWMGKDKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₉
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.17333247 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.78
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8274	82.74%
Caco-2	-	0.7610	76.10%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8614	86.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8404	84.04%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5659	56.59%
P-glycoprotein inhibitior	-	0.6509	65.09%
P-glycoprotein substrate	-	0.8336	83.36%
CYP3A4 substrate	+	0.6348	63.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.7735	77.35%
CYP2C9 inhibition	-	0.8826	88.26%
CYP2C19 inhibition	-	0.8354	83.54%
CYP2D6 inhibition	-	0.9029	90.29%
CYP1A2 inhibition	-	0.8908	89.08%
CYP2C8 inhibition	-	0.7971	79.71%
CYP inhibitory promiscuity	-	0.9650	96.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7626	76.26%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9516	95.16%
Skin irritation	-	0.7473	74.73%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4144	41.44%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5518	55.18%
skin sensitisation	-	0.8389	83.89%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5619	56.19%
Acute Oral Toxicity (c)	III	0.6643	66.43%
Estrogen receptor binding	+	0.7640	76.40%
Androgen receptor binding	-	0.6972	69.72%
Thyroid receptor binding	+	0.6435	64.35%
Glucocorticoid receptor binding	-	0.5448	54.48%
Aromatase binding	+	0.5571	55.71%
PPAR gamma	+	0.5268	52.68%
Honey bee toxicity	-	0.6720	67.20%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.6917	69.17%

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	93.74%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.11%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.43%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.20%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	87.05%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.19%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.09%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.51%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.00%	89.00%

Plants that contains it

• Tetraneuris ivesiana

Cross-Links

• PubChem: 162951578
• LOTUS: LTS0225007
• wikiData: Q104975766