(25R)-3beta-[4-O-[2-O-beta-D-Glucopyranosyl-3-O-(4-O-alpha-L-rhamnopyranosyl-beta-D-xylopyranosyl)-beta-D-glucopyranosyl]-beta-D-galactopyranosyloxy]-5alpha-spirostan-2alpha-ol

Details

• Internal ID: 5f34c98c-0a90-4b51-a245-34709a5db2ab
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(3R,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-15-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CC(C(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)OC2C(C(C(C(O2)C)O)O)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)C)C)C)OC1
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(C[C@H]([C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C)O)O)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)C)C)C)OC1
• InChI: InChI=1S/C56H92O27/c1-20-8-11-56(73-18-20)21(2)34-29(83-56)13-26-24-7-6-23-12-28(27(60)14-55(23,5)25(24)9-10-54(26,34)4)75-51-45(71)41(67)46(32(17-59)78-51)80-53-48(82-52-44(70)40(66)36(62)30(15-57)76-52)47(38(64)31(16-58)77-53)81-49-42(68)37(63)33(19-72-49)79-50-43(69)39(65)35(61)22(3)74-50/h20-53,57-71H,6-19H2,1-5H3/t20-,21+,22+,23+,24-,25+,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-,52+,53+,54+,55+,56-/m1/s1
• InChI Key: NKJKUGAKHPNGTM-GZMVBOFVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₉₂O₂₇
• Molecular Weight: 1197.30 g/mol
• Exact Mass: 1196.58259765 g/mol
• Topological Polar Surface Area (TPSA): 414.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -4.45
• H-Bond Acceptor: 27
• H-Bond Donor: 15
• Rotatable Bonds: 13

Synonyms

• (25R)-3beta-[4-O-[2-O-beta-D-Glucopyranosyl-3-O-(4-O-alpha-L-rhamnopyranosyl-beta-D-xylopyranosyl)-beta-D-glucopyranosyl]-beta-D-galactopyranosyloxy]-5alpha-spirostan-2alpha-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5246	52.46%
Caco-2	-	0.8749	87.49%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6174	61.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8830	88.30%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.9019	90.19%
P-glycoprotein inhibitior	+	0.7398	73.98%
P-glycoprotein substrate	-	0.6811	68.11%
CYP3A4 substrate	+	0.7549	75.49%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8164	81.64%
CYP3A4 inhibition	-	0.9473	94.73%
CYP2C9 inhibition	-	0.9215	92.15%
CYP2C19 inhibition	-	0.8997	89.97%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.9215	92.15%
CYP2C8 inhibition	+	0.7435	74.35%
CYP inhibitory promiscuity	-	0.9616	96.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6223	62.23%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.6555	65.55%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8110	81.10%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.9420	94.20%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.9259	92.59%
Acute Oral Toxicity (c)	I	0.8185	81.85%
Estrogen receptor binding	+	0.8785	87.85%
Androgen receptor binding	+	0.7187	71.87%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.6382	63.82%
Aromatase binding	+	0.6429	64.29%
PPAR gamma	+	0.7917	79.17%
Honey bee toxicity	-	0.5155	51.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7523	75.23%

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	98.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.73%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.84%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.83%	97.09%
CHEMBL237	P41145	Kappa opioid receptor	92.95%	98.10%
CHEMBL226	P30542	Adenosine A1 receptor	92.81%	95.93%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	92.70%	97.31%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.68%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.33%	95.50%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	92.27%	95.58%
CHEMBL204	P00734	Thrombin	92.08%	96.01%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.97%	100.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	91.90%	97.86%
CHEMBL233	P35372	Mu opioid receptor	90.87%	97.93%
CHEMBL259	P32245	Melanocortin receptor 4	89.06%	95.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.72%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.61%	89.05%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.49%	92.86%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.80%	93.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.21%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	86.05%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.02%	94.45%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.84%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.13%	95.83%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	84.78%	95.36%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	83.94%	96.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.74%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	83.50%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.31%	86.33%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	83.21%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	82.31%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.94%	86.92%
CHEMBL3714531	Q6P988	Palmitoleoyl-protein carboxylesterase NOTUM	81.93%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.40%	97.28%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.28%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.04%	91.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.19%	92.94%

Plants that contains it

• Aframomum zambesiacum
• Alisma plantago-aquatica
• Ambrosia cumanensis
• Angostura granulosa
• Buckiella undulata
• Chamaecrista dentata
• Clausena anisum-olens
• Clinostemon mahuba
• Dioscorea cirrhosa
• Echinops bannaticus
• Euonymus lucidus
• Euphorbia lamprocarpa
• Ferula transiliensis
• Fraxinus angustifolia
• Genista hystrix
• Helichrysum anomalum
• Heptapleurum bodinieri
• Hippomane mancinella
• Hosta longipes
• Hosta plantaginea
• Hosta sieboldii
• Isatis costata
• Kartalinia acaulis
• Machilus thunbergii
• Prunus sibirica
• Rhododendron ponticum
• Senecio roseus
• Seriphidium aucheri
• Speranskia tuberculata
• Veronica hederifolia
• Viguiera dentata
• Yucca gloriosa

Cross-Links

• PubChem: 71716476
• NPASS: NPC83137
• ChEMBL: CHEMBL2337723
• LOTUS: LTS0134769
• wikiData: Q105180620