(R)-4alpha-[(R)-3-[[6-O-(D-Apio-beta-D-furanosyl)-beta-D-glucopyranosyl]oxy]-1-butenyl]-3,5,5-trimethylcyclohexa-2-en-1-one

Details

• Internal ID: 43e951f7-04ab-430f-ad0a-4af275a6d72a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (4R)-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1C=CC(C)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O)(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)CO[C@H]3[C@@H]([C@](CO3)(CO)O)O)O)O)O)(C)C
• InChI: InChI=1S/C24H38O11/c1-12-7-14(26)8-23(3,4)15(12)6-5-13(2)34-21-19(29)18(28)17(27)16(35-21)9-32-22-20(30)24(31,10-25)11-33-22/h5-7,13,15-22,25,27-31H,8-11H2,1-4H3/b6-5+/t13-,15+,16-,17-,18+,19-,20+,21-,22-,24-/m1/s1
• InChI Key: DQQUPMXQGJRNAW-LCIZJANLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₈O₁₁
• Molecular Weight: 502.60 g/mol
• Exact Mass: 502.24141202 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• (6R,7E,9R)-9-Hydroxy-4,7-megastigmadien-3-one 9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside
• 143363-62-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5387	53.87%
Caco-2	-	0.8409	84.09%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7982	79.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8722	87.22%
OATP1B3 inhibitior	+	0.9028	90.28%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8129	81.29%
P-glycoprotein inhibitior	-	0.5874	58.74%
P-glycoprotein substrate	-	0.6443	64.43%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.9239	92.39%
CYP2C9 inhibition	-	0.8365	83.65%
CYP2C19 inhibition	-	0.8635	86.35%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9040	90.40%
CYP2C8 inhibition	-	0.6133	61.33%
CYP inhibitory promiscuity	-	0.8525	85.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9621	96.21%
Skin irritation	-	0.7451	74.51%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6508	65.08%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.8269	82.69%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4817	48.17%
Acute Oral Toxicity (c)	III	0.5486	54.86%
Estrogen receptor binding	+	0.6316	63.16%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5947	59.47%
Glucocorticoid receptor binding	-	0.4861	48.61%
Aromatase binding	+	0.6493	64.93%
PPAR gamma	+	0.6683	66.83%
Honey bee toxicity	-	0.7703	77.03%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8427	84.27%

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	98.96%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.20%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.98%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.92%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.04%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.99%	96.47%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.43%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.34%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.13%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.01%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.64%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.60%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	86.35%	94.73%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.96%	98.75%
CHEMBL1871	P10275	Androgen Receptor	85.39%	96.43%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.16%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.82%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.73%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.60%	94.45%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.60%	97.47%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.40%	89.34%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.27%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.65%	95.89%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.31%	92.32%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.19%	91.07%

Plants that contains it

• Alangium premnifolium

Cross-Links

• PubChem: 101924224
• LOTUS: LTS0050817
• wikiData: Q104987085