(22R,25R)-3beta-(2-O,4-O-Di-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-26-(beta-D-glucopyranosyloxy)cholesta-5-ene-22-ol

Details

• Internal ID: 558d04bc-d3a4-4c8e-aad7-e5591a34dcec
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,6R)-3-hydroxy-6-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)OC3C(C(C(C(O3)C)O)O)O)OC4CCC5(C6CCC7(C(C6CC=C5C4)CCC7C(C)C(CCC(C)COC8C(C(C(C(O8)CO)O)O)O)O)C)C)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)O[C@H]4CC[C@@]5([C@H]6CC[C@]7([C@H]([C@@H]6CC=C5C4)CC[C@@H]7[C@H](C)[C@@H](CC[C@@H](C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)C)C)CO)O)O)O
• InChI: InChI=1S/C51H86O21/c1-21(20-65-46-40(61)39(60)36(57)32(18-52)69-46)7-12-31(54)22(2)28-10-11-29-27-9-8-25-17-26(13-15-50(25,5)30(27)14-16-51(28,29)6)68-49-45(72-48-42(63)38(59)35(56)24(4)67-48)43(64)44(33(19-53)70-49)71-47-41(62)37(58)34(55)23(3)66-47/h8,21-24,26-49,52-64H,7,9-20H2,1-6H3/t21-,22+,23+,24+,26+,27+,28-,29+,30+,31-,32-,33-,34+,35+,36-,37-,38-,39+,40-,41-,42-,43+,44-,45-,46-,47+,48+,49-,50+,51-/m1/s1
• InChI Key: YUAPCVBXJPIAQW-ATVJSTEASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₆O₂₁
• Molecular Weight: 1035.20 g/mol
• Exact Mass: 1034.56615975 g/mol
• Topological Polar Surface Area (TPSA): 337.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6996	69.96%
Caco-2	-	0.8865	88.65%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7115	71.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8753	87.53%
OATP1B3 inhibitior	+	0.8307	83.07%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8030	80.30%
P-glycoprotein inhibitior	+	0.7392	73.92%
P-glycoprotein substrate	+	0.6483	64.83%
CYP3A4 substrate	+	0.7384	73.84%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9514	95.14%
CYP2C9 inhibition	-	0.9263	92.63%
CYP2C19 inhibition	-	0.9276	92.76%
CYP2D6 inhibition	-	0.9433	94.33%
CYP1A2 inhibition	-	0.9189	91.89%
CYP2C8 inhibition	+	0.7054	70.54%
CYP inhibitory promiscuity	-	0.9488	94.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6030	60.30%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9062	90.62%
Skin irritation	-	0.5271	52.71%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8273	82.73%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9222	92.22%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9415	94.15%
Acute Oral Toxicity (c)	I	0.4859	48.59%
Estrogen receptor binding	+	0.8682	86.82%
Androgen receptor binding	+	0.7594	75.94%
Thyroid receptor binding	+	0.5393	53.93%
Glucocorticoid receptor binding	+	0.6717	67.17%
Aromatase binding	+	0.6987	69.87%
PPAR gamma	+	0.7869	78.69%
Honey bee toxicity	-	0.6559	65.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9013	90.13%

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	99.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.72%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.60%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.46%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.15%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.43%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.06%	89.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	90.11%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.66%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.59%	89.05%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.47%	97.36%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.01%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	87.38%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.22%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.06%	86.33%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.90%	97.29%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.89%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.09%	94.45%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.59%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.95%	94.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.50%	98.46%
CHEMBL332	P03956	Matrix metalloproteinase-1	80.61%	94.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.53%	100.00%

Plants that contains it

• Solanum viarum

Cross-Links

• PubChem: 44130319
• LOTUS: LTS0089335
• wikiData: Q105362539