(2S,3R,4S,5R,6R)-2-[(1S,3R,4R)-3,4-dihydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohexyl]oxy-6-[[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol

Details

• Internal ID: 424e8686-c8c8-45ef-b10d-dbaf197947fe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2S,3R,4S,5R,6R)-2-[(1S,3R,4R)-3,4-dihydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohexyl]oxy-6-[[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): CC(C=CC1(C(CC(CC1(C)O)OC2C(C(C(C(O2)COC3C(C(C(CO3)O)O)O)O)O)O)(C)C)O)O
• SMILES (Isomeric): C[C@H](/C=C/[C@@]1([C@](C[C@H](CC1(C)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)O)O)O
• InChI: InChI=1S/C24H42O13/c1-11(25)5-6-24(33)22(2,3)7-12(8-23(24,4)32)36-21-19(31)17(29)16(28)14(37-21)10-35-20-18(30)15(27)13(26)9-34-20/h5-6,11-21,25-33H,7-10H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,17+,18+,19-,20-,21+,23-,24-/m1/s1
• InChI Key: RIHVUVZNBNYDHR-RRVXYRROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₂O₁₃
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.26254139 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -3.13
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7816	78.16%
Caco-2	-	0.8506	85.06%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7439	74.39%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.8997	89.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7796	77.96%
P-glycoprotein inhibitior	-	0.5652	56.52%
P-glycoprotein substrate	-	0.6612	66.12%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.9706	97.06%
CYP2C9 inhibition	-	0.8751	87.51%
CYP2C19 inhibition	-	0.8934	89.34%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9177	91.77%
CYP2C8 inhibition	-	0.7594	75.94%
CYP inhibitory promiscuity	-	0.9452	94.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.8332	83.32%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3747	37.47%
Micronuclear	-	0.7926	79.26%
Hepatotoxicity	-	0.7371	73.71%
skin sensitisation	-	0.8407	84.07%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9382	93.82%
Acute Oral Toxicity (c)	III	0.6463	64.63%
Estrogen receptor binding	+	0.6507	65.07%
Androgen receptor binding	+	0.5524	55.24%
Thyroid receptor binding	+	0.5689	56.89%
Glucocorticoid receptor binding	+	0.5840	58.40%
Aromatase binding	+	0.6820	68.20%
PPAR gamma	+	0.5661	56.61%
Honey bee toxicity	-	0.7255	72.55%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.7726	77.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.74%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.55%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	95.37%	95.93%
CHEMBL2179	P04062	Beta-glucocerebrosidase	94.56%	85.31%
CHEMBL1951	P21397	Monoamine oxidase A	89.15%	91.49%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.82%	96.47%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.35%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.05%	97.09%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.91%	92.32%
CHEMBL2581	P07339	Cathepsin D	85.78%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.45%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	84.86%	94.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.32%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.60%	96.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.41%	95.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.46%	93.10%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.65%	95.89%
CHEMBL5957	P21589	5'-nucleotidase	80.06%	97.78%

Plants that contains it

• Alangium premnifolium

Cross-Links

• PubChem: 162857244
• LOTUS: LTS0074457
• wikiData: Q104909202