(4R)-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxybut-1-enyl]cyclohex-2-en-1-one

Details

• Internal ID: 0a674924-5a00-41fa-8e2e-91cffea8d97f
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (4R)-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxybut-1-enyl]cyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1C=CC(C)OC2C(C(C(C(O2)COC3C(C(C(CO3)O)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@H]([C@@H](CO3)O)O)O)O)O)O)(C)C
• InChI: InChI=1S/C24H38O11/c1-11-7-13(25)8-24(3,4)14(11)6-5-12(2)34-23-21(31)19(29)18(28)16(35-23)10-33-22-20(30)17(27)15(26)9-32-22/h5-7,12,14-23,26-31H,8-10H2,1-4H3/b6-5+/t12-,14+,15-,16-,17+,18-,19+,20-,21-,22+,23-/m1/s1
• InChI Key: FFYPJOJFUJFYAT-AWZIMYOFSA-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: -2.00
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• CHEBI:182937
• DTXSID701317219
• 290308-51-9
• C17888

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5506	55.06%
Caco-2	-	0.8519	85.19%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8270	82.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8712	87.12%
OATP1B3 inhibitior	+	0.8674	86.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8072	80.72%
P-glycoprotein inhibitior	-	0.6449	64.49%
P-glycoprotein substrate	-	0.6888	68.88%
CYP3A4 substrate	+	0.6683	66.83%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8862	88.62%
CYP3A4 inhibition	-	0.9757	97.57%
CYP2C9 inhibition	-	0.8378	83.78%
CYP2C19 inhibition	-	0.8494	84.94%
CYP2D6 inhibition	-	0.9351	93.51%
CYP1A2 inhibition	-	0.9112	91.12%
CYP2C8 inhibition	-	0.7279	72.79%
CYP inhibitory promiscuity	-	0.9328	93.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6345	63.45%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9659	96.59%
Skin irritation	-	0.7751	77.51%
Skin corrosion	-	0.9537	95.37%
Ames mutagenesis	+	0.5546	55.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7384	73.84%
Micronuclear	-	0.7826	78.26%
Hepatotoxicity	-	0.7146	71.46%
skin sensitisation	-	0.7830	78.30%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8242	82.42%
Acute Oral Toxicity (c)	III	0.6819	68.19%
Estrogen receptor binding	+	0.6030	60.30%
Androgen receptor binding	-	0.5758	57.58%
Thyroid receptor binding	+	0.5830	58.30%
Glucocorticoid receptor binding	-	0.5367	53.67%
Aromatase binding	+	0.5644	56.44%
PPAR gamma	+	0.6589	65.89%
Honey bee toxicity	-	0.7722	77.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8784	87.84%

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	99.15%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.26%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.89%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.12%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.53%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.45%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.60%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL1871	P10275	Androgen Receptor	88.28%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.93%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.44%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.24%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.73%	96.47%
CHEMBL4040	P28482	MAP kinase ERK2	84.57%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.20%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.78%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.92%	89.34%
CHEMBL1937	Q92769	Histone deacetylase 2	81.69%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.45%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.03%	89.62%

Plants that contains it

• Eriobotrya japonica

Cross-Links

• PubChem: 9892275
• LOTUS: LTS0052732
• wikiData: Q104994739