1-[(2R,3R,8R,9S,10R,13S,14S)-3-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

Details

• Internal ID: 54e2e60e-3ba6-4fb5-9837-dca210481dd1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 1-[(2R,3R,8R,9S,10R,13S,14S)-3-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• SMILES (Canonical): CC(=O)C1=CCC2C1(CCC3C2CC=C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)OC6C(C(C(C(O6)CO)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)O)C)C
• SMILES (Isomeric): CC(=O)C1=CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(C[C@H]([C@@H](C4)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)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]([C@H](O9)CO)O)O)O)O)O)O)O)C)C
• InChI: InChI=1S/C50H78O27/c1-17(55)20-6-7-21-19-5-4-18-10-25(23(56)11-50(18,3)22(19)8-9-49(20,21)2)69-45-38(66)35(63)40(29(15-54)73-45)74-48-43(42(33(61)28(14-53)72-48)76-44-36(64)30(58)24(57)16-68-44)77-47-39(67)41(32(60)27(13-52)71-47)75-46-37(65)34(62)31(59)26(12-51)70-46/h4,6,19,21-48,51-54,56-67H,5,7-16H2,1-3H3/t19-,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-/m0/s1
• InChI Key: AZDNJBBUCLAIIW-IYCNBSOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₈O₂₇
• Molecular Weight: 1111.10 g/mol
• Exact Mass: 1110.47304721 g/mol
• Topological Polar Surface Area (TPSA): 433.00 Ų
• XlogP: -5.50
• Atomic LogP (AlogP): -6.83
• H-Bond Acceptor: 27
• H-Bond Donor: 16
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7838	78.38%
Caco-2	-	0.8734	87.34%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8582	85.82%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.9579	95.79%
P-glycoprotein inhibitior	+	0.7346	73.46%
P-glycoprotein substrate	+	0.5699	56.99%
CYP3A4 substrate	+	0.7377	73.77%
CYP2C9 substrate	-	0.7956	79.56%
CYP2D6 substrate	-	0.8844	88.44%
CYP3A4 inhibition	-	0.9495	94.95%
CYP2C9 inhibition	-	0.9335	93.35%
CYP2C19 inhibition	-	0.9392	93.92%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9243	92.43%
CYP2C8 inhibition	+	0.7191	71.91%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9040	90.40%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8098	80.98%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8690	86.90%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.8355	83.55%
Androgen receptor binding	+	0.7426	74.26%
Thyroid receptor binding	+	0.5174	51.74%
Glucocorticoid receptor binding	+	0.6574	65.74%
Aromatase binding	+	0.6158	61.58%
PPAR gamma	+	0.7809	78.09%
Honey bee toxicity	-	0.5889	58.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9296	92.96%

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	98.78%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.73%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.10%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	93.58%	91.24%
CHEMBL226	P30542	Adenosine A1 receptor	93.09%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.02%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.26%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	89.66%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.51%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.03%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.24%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.47%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.31%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.85%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.11%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.33%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.30%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.26%	94.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.38%	89.05%

Plants that contains it

• Cestrum nocturnum

Cross-Links

• PubChem: 11094376
• LOTUS: LTS0250185
• wikiData: Q104921619