(2R,3R,4S,5S,6R)-2-[4-[(1R,2S,4S,8S,9S,12S,13S,16S,18R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 0cbcfce7-fc5a-445b-9631-b5d945858549
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[4-[(1R,2S,4S,8S,9S,12S,13S,16S,18R)-16-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-6-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1=C(OC2C1C3(CCC4C(C3C2)CCC5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C)CCC(C)COC8C(C(C(C(O8)CO)O)O)O
• SMILES (Isomeric): CC1=C(O[C@@H]2[C@H]1[C@]3(CC[C@H]4[C@H]([C@@H]3C2)CC[C@H]5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)CCC(C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C45H74O18/c1-19(18-57-41-38(55)35(52)32(49)28(15-46)60-41)5-8-26-20(2)31-27(59-26)14-25-23-7-6-21-13-22(9-11-44(21,3)24(23)10-12-45(25,31)4)58-43-40(37(54)34(51)30(17-48)62-43)63-42-39(56)36(53)33(50)29(16-47)61-42/h19,21-25,27-43,46-56H,5-18H2,1-4H3/t19?,21-,22+,23-,24+,25+,27+,28-,29-,30-,31+,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,42+,43-,44+,45+/m1/s1
• InChI Key: ROHLIYKWVMBBFX-JOJGKSKXSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₄O₁₈
• Molecular Weight: 903.10 g/mol
• Exact Mass: 902.48751551 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

• 139051-27-7
• 3beta-[(2-O-beta-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy]-26-(beta-D-glucopyranosyloxy)-5beta-furost-20(22)-ene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6445	64.45%
Caco-2	-	0.8852	88.52%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7407	74.07%
OATP2B1 inhibitior	-	0.8713	87.13%
OATP1B1 inhibitior	+	0.8652	86.52%
OATP1B3 inhibitior	+	0.9071	90.71%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6097	60.97%
P-glycoprotein inhibitior	+	0.7367	73.67%
P-glycoprotein substrate	+	0.5544	55.44%
CYP3A4 substrate	+	0.7421	74.21%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8244	82.44%
CYP3A4 inhibition	-	0.9512	95.12%
CYP2C9 inhibition	-	0.9111	91.11%
CYP2C19 inhibition	-	0.9033	90.33%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.8836	88.36%
CYP2C8 inhibition	+	0.6099	60.99%
CYP inhibitory promiscuity	-	0.8713	87.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5860	58.60%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9107	91.07%
Skin irritation	-	0.5827	58.27%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.7838	78.38%
Human Ether-a-go-go-Related Gene inhibition	+	0.8279	82.79%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9241	92.41%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9177	91.77%
Acute Oral Toxicity (c)	I	0.6824	68.24%
Estrogen receptor binding	+	0.8197	81.97%
Androgen receptor binding	+	0.7479	74.79%
Thyroid receptor binding	-	0.5298	52.98%
Glucocorticoid receptor binding	+	0.5931	59.31%
Aromatase binding	+	0.6622	66.22%
PPAR gamma	+	0.7241	72.41%
Honey bee toxicity	-	0.5983	59.83%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9372	93.72%

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	97.23%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.41%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.14%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.61%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.04%	97.79%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.04%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.72%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.50%	96.38%
CHEMBL237	P41145	Kappa opioid receptor	88.98%	98.10%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.37%	92.86%
CHEMBL4581	P52732	Kinesin-like protein 1	88.35%	93.18%
CHEMBL226	P30542	Adenosine A1 receptor	88.02%	95.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.81%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.74%	96.47%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.52%	100.00%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	87.42%	91.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.73%	95.89%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.39%	98.05%
CHEMBL206	P03372	Estrogen receptor alpha	84.78%	97.64%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.03%	96.61%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	83.83%	95.58%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.78%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.76%	95.89%
CHEMBL233	P35372	Mu opioid receptor	81.74%	97.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.71%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.45%	89.00%
CHEMBL2514	O95665	Neurotensin receptor 2	81.34%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.78%	92.50%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.51%	96.37%
CHEMBL1937	Q92769	Histone deacetylase 2	80.05%	94.75%

Plants that contains it

• Anemarrhena asphodeloides

Cross-Links

• PubChem: 71307555
• NPASS: NPC130873