(25R)-1beta-(2-O-alpha-L-Rhamnopyranosyl-alpha-L-arabinopyranosyloxy)spirosta-5-ene-3beta-ol

Details

• Internal ID: dc06b91c-7816-42c8-95b4-ba3ab8d4d484
• 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,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(C(CC(C6)O)OC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)C)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=C6[C@@]5([C@@H](C[C@@H](C6)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)C)OC1
• InChI: InChI=1S/C38H60O12/c1-17-8-11-38(46-15-17)18(2)28-26(50-38)14-24-22-7-6-20-12-21(39)13-27(37(20,5)23(22)9-10-36(24,28)4)48-35-33(30(42)25(40)16-45-35)49-34-32(44)31(43)29(41)19(3)47-34/h6,17-19,21-35,39-44H,7-16H2,1-5H3/t17-,18+,19+,21-,22-,23+,24+,25+,26+,27-,28+,29+,30+,31-,32-,33-,34+,35+,36+,37+,38-/m1/s1
• InChI Key: SKHJNNFXCKTDBG-QUNJDNMZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₀O₁₂
• Molecular Weight: 708.90 g/mol
• Exact Mass: 708.40847734 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• (25R)-1beta-(2-O-alpha-L-Rhamnopyranosyl-alpha-L-arabinopyranosyloxy)spirosta-5-ene-3beta-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8924	89.24%
Caco-2	-	0.8733	87.33%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7436	74.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8784	87.84%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.5939	59.39%
P-glycoprotein inhibitior	+	0.6984	69.84%
P-glycoprotein substrate	+	0.5934	59.34%
CYP3A4 substrate	+	0.7551	75.51%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8129	81.29%
CYP3A4 inhibition	-	0.9509	95.09%
CYP2C9 inhibition	-	0.9165	91.65%
CYP2C19 inhibition	-	0.9392	93.92%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.9062	90.62%
CYP2C8 inhibition	+	0.7578	75.78%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5064	50.64%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9260	92.60%
Skin irritation	-	0.5793	57.93%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7685	76.85%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8919	89.19%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8048	80.48%
Acute Oral Toxicity (c)	I	0.4810	48.10%
Estrogen receptor binding	+	0.7556	75.56%
Androgen receptor binding	+	0.7192	71.92%
Thyroid receptor binding	-	0.6152	61.52%
Glucocorticoid receptor binding	-	0.4941	49.41%
Aromatase binding	+	0.6950	69.50%
PPAR gamma	+	0.6596	65.96%
Honey bee toxicity	-	0.5574	55.74%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9449	94.49%

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	98.35%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	97.02%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.54%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.41%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.61%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.24%	100.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	91.39%	94.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.38%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.59%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.21%	95.89%
CHEMBL1914	P06276	Butyrylcholinesterase	88.65%	95.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.93%	90.17%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.20%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	83.56%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.08%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.45%	97.28%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.04%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	81.40%	92.50%
CHEMBL2581	P07339	Cathepsin D	81.38%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.37%	92.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.03%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.89%	94.00%
CHEMBL5028	O14672	ADAM10	80.78%	97.50%

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 concinna
• Erinus alpinus
• Fritillaria taipaiensis
• Geranium macrorrhizum
• Gypothamnium pinifolium
• Hypolaena fastigiata
• Maclura pomifera
• Meryta denhamii
• Mimosa invisa
• Morinda citrifolia
• Ornithogalum thyrsoides
• Pedicularis densispica
• Penianthus zenkeri
• Ruscus aculeatus
• Senecio macrophyllus
• Solanum chacoense
• Stenostomum acutatum
• Timonius eximius

Cross-Links

• PubChem: 44575746
• NPASS: NPC70204
• LOTUS: LTS0159067
• wikiData: Q105254819