[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E,2R)-4-[(1S)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]but-3-en-2-yl]oxyoxan-2-yl]methyl acetate

Details

• Internal ID: 8de78a20-2a49-4ad8-b9b2-6f9a6c774184
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E,2R)-4-[(1S)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]but-3-en-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1=CC(=O)CC(C1C=CC(C)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@@H]1/C=C/[C@@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)(C)C
• InChI: InChI=1S/C27H38O11/c1-14-11-20(32)12-27(7,8)21(14)10-9-15(2)34-26-25(37-19(6)31)24(36-18(5)30)23(35-17(4)29)22(38-26)13-33-16(3)28/h9-11,15,21-26H,12-13H2,1-8H3/b10-9+/t15-,21-,22-,23-,24+,25-,26-/m1/s1
• InChI Key: NILGFPDWHHOUSF-IOLHSJAOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₁
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.24141202 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9709	97.09%
Caco-2	-	0.7251	72.51%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.8419	84.19%
OATP1B3 inhibitior	+	0.8822	88.22%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9587	95.87%
P-glycoprotein inhibitior	+	0.8611	86.11%
P-glycoprotein substrate	-	0.8034	80.34%
CYP3A4 substrate	+	0.6664	66.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9030	90.30%
CYP3A4 inhibition	-	0.8800	88.00%
CYP2C9 inhibition	-	0.7467	74.67%
CYP2C19 inhibition	-	0.6858	68.58%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.6625	66.25%
CYP2C8 inhibition	-	0.7340	73.40%
CYP inhibitory promiscuity	-	0.6459	64.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8628	86.28%
Carcinogenicity (trinary)	Non-required	0.5620	56.20%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.7346	73.46%
Skin corrosion	-	0.9608	96.08%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7194	71.94%
Micronuclear	-	0.6226	62.26%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.5765	57.65%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.4744	47.44%
Acute Oral Toxicity (c)	III	0.5852	58.52%
Estrogen receptor binding	+	0.6884	68.84%
Androgen receptor binding	-	0.5218	52.18%
Thyroid receptor binding	+	0.5746	57.46%
Glucocorticoid receptor binding	+	0.7265	72.65%
Aromatase binding	+	0.5726	57.26%
PPAR gamma	+	0.6573	65.73%
Honey bee toxicity	-	0.7994	79.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9661	96.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.16%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.84%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.36%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.95%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.57%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.14%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	88.04%	92.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.49%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.21%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.72%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.78%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.57%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.95%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.70%	100.00%
CHEMBL5028	O14672	ADAM10	81.63%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.54%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.28%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.16%	94.80%
CHEMBL226	P30542	Adenosine A1 receptor	80.82%	95.93%
CHEMBL1871	P10275	Androgen Receptor	80.46%	96.43%

Plants that contains it

• Rosa transmorrisonensis

Cross-Links

• PubChem: 163021930
• LOTUS: LTS0035592
• wikiData: Q105179876