1beta-[(2-O-alpha-L-Rhamnopyranosyl-alpha-L-arabinopyranosyl)oxy]-26-(beta-D-glucopyranosyloxy)furosta-5,20(22),25(27)-trien-3beta-ol

Details

• Internal ID: e4a7a485-9cfe-464a-a7ea-7e2cfc8ffdfe
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S)-4,5-dihydroxy-2-[[(1S,2S,4S,8S,9S,12S,13R,14R,16R)-16-hydroxy-7,9,13-trimethyl-6-[3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]but-3-enyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,18-dien-14-yl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CC(CC4=CCC5C(C34C)CCC6(C5CC7C6C(=C(O7)CCC(=C)COC8C(C(C(C(O8)CO)O)O)O)C)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@@H]3C[C@@H](CC4=CC[C@@H]5[C@@H]([C@@]34C)CC[C@]6([C@H]5C[C@H]7[C@@H]6C(=C(O7)CCC(=C)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)O)O)O)O)O)O
• InChI: InChI=1S/C44H68O17/c1-18(16-55-40-37(53)36(52)34(50)29(15-45)59-40)6-9-27-19(2)31-28(58-27)14-25-23-8-7-21-12-22(46)13-30(44(21,5)24(23)10-11-43(25,31)4)60-42-39(33(49)26(47)17-56-42)61-41-38(54)35(51)32(48)20(3)57-41/h7,20,22-26,28-42,45-54H,1,6,8-17H2,2-5H3/t20-,22+,23+,24-,25-,26-,28-,29+,30+,31-,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43-,44-/m0/s1
• InChI Key: YCXHBSHHBWHZKV-FUNUAUJQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₈O₁₇
• Molecular Weight: 869.00 g/mol
• Exact Mass: 868.44565070 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• 1beta-[(2-O-alpha-L-Rhamnopyranosyl-alpha-L-arabinopyranosyl)oxy]-26-(beta-D-glucopyranosyloxy)furosta-5,20(22),25(27)-trien-3beta-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7345	73.45%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6911	69.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8427	84.27%
OATP1B3 inhibitior	+	0.8909	89.09%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8632	86.32%
P-glycoprotein inhibitior	+	0.7355	73.55%
P-glycoprotein substrate	+	0.7131	71.31%
CYP3A4 substrate	+	0.7558	75.58%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.8297	82.97%
CYP3A4 inhibition	-	0.9006	90.06%
CYP2C9 inhibition	-	0.9010	90.10%
CYP2C19 inhibition	-	0.9027	90.27%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.8983	89.83%
CYP2C8 inhibition	+	0.8221	82.21%
CYP inhibitory promiscuity	-	0.9325	93.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5433	54.33%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9112	91.12%
Skin irritation	+	0.5100	51.00%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.6291	62.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7947	79.47%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9094	90.94%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9587	95.87%
Acute Oral Toxicity (c)	I	0.5214	52.14%
Estrogen receptor binding	+	0.8255	82.55%
Androgen receptor binding	+	0.7359	73.59%
Thyroid receptor binding	-	0.5383	53.83%
Glucocorticoid receptor binding	+	0.6509	65.09%
Aromatase binding	+	0.6865	68.65%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.5710	57.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9570	95.70%

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	97.52%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.13%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.07%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.82%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.70%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.65%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.64%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.67%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.92%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.99%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.70%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.52%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.32%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.84%	99.17%
CHEMBL5028	O14672	ADAM10	83.64%	97.50%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.59%	96.25%
CHEMBL4208	P20618	Proteasome component C5	83.30%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.14%	97.36%
CHEMBL1871	P10275	Androgen Receptor	83.09%	96.43%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.35%	96.37%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.62%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.34%	92.50%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.53%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.35%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.33%	96.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.31%	95.00%

Plants that contains it

• Adina eurhyncha
• Agave parryi var. huachucensis
• Aloe vera
• Angiopteris helferiana
• Anisomeles indica
• Anomospermum grandifolium
• Catunaregam longispina
• Centaurea diffusa
• Clarkia unguiculata
• Dahlstedtia pinnata
• Daphne papyracea
• Dermatophyllum secundiflorum
• Dracaena angustifolia
• Dracaena cambodiana
• Erinus alpinus
• Fritillaria taipaiensis
• Geranium macrorrhizum
• Gypothamnium pinifolium
• Hypolaena fastigiata
• Maclura pomifera
• Meryta denhamii
• Mimosa invisa
• Morinda citrifolia
• Pedicularis densispica
• Penianthus zenkeri
• Ruscus aculeatus
• Senecio macrophyllus
• Solanum chacoense
• Stenostomum acutatum
• Timonius eximius

Cross-Links

• PubChem: 44567205
• NPASS: NPC148965
• LOTUS: LTS0161790
• wikiData: Q105346565