(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[(1S)-1-[(3S,8S,9S,10R,13S,14S,16R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-5-hydroxy-4-methoxy-6-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 24123928-3cdc-4e58-9049-54ba4e98a502
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[(1S)-1-[(3S,8S,9S,10R,13S,14S,16R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-16-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-5-hydroxy-4-methoxy-6-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(CC2OC)OC3CCC4(C5CCC6(C(C5CC=C4C3)CC(C6C(C)OC7C(C(C(C(O7)C)O)OC)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)O)C)C)C)O)OC)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[C@@H]2OC)O[C@H]3CC[C@@]4([C@H]5CC[C@]6([C@H]([C@@H]5CC=C4C3)C[C@H]([C@@H]6[C@H](C)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)C)O)OC)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O)O)C)C)C)O)OC)O
• InChI: InChI=1S/C54H90O24/c1-21(71-52-48(47(68-9)37(58)23(3)73-52)78-50-43(64)41(62)39(60)33(76-50)20-69-49-42(63)40(61)38(59)32(19-55)75-49)35-30(56)17-29-27-11-10-25-16-26(12-14-53(25,5)28(27)13-15-54(29,35)6)74-34-18-31(66-7)45(24(4)70-34)77-51-44(65)46(67-8)36(57)22(2)72-51/h10,21-24,26-52,55-65H,11-20H2,1-9H3/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-,52+,53-,54-/m0/s1
• InChI Key: CHIRAQOIZROZGK-AENPZXLLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₀O₂₄
• Molecular Weight: 1123.30 g/mol
• Exact Mass: 1122.58220373 g/mol
• Topological Polar Surface Area (TPSA): 343.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.53
• H-Bond Acceptor: 24
• H-Bond Donor: 11
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6883	68.83%
Caco-2	-	0.8796	87.96%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6871	68.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8704	87.04%
OATP1B3 inhibitior	+	0.8726	87.26%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9321	93.21%
P-glycoprotein inhibitior	+	0.7451	74.51%
P-glycoprotein substrate	+	0.7361	73.61%
CYP3A4 substrate	+	0.7457	74.57%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8331	83.31%
CYP3A4 inhibition	-	0.9630	96.30%
CYP2C9 inhibition	-	0.9225	92.25%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.9167	91.67%
CYP2C8 inhibition	+	0.7187	71.87%
CYP inhibitory promiscuity	-	0.9551	95.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6001	60.01%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9033	90.33%
Skin irritation	-	0.5781	57.81%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8454	84.54%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9142	91.42%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9209	92.09%
Acute Oral Toxicity (c)	I	0.4817	48.17%
Estrogen receptor binding	+	0.8465	84.65%
Androgen receptor binding	+	0.7166	71.66%
Thyroid receptor binding	+	0.5674	56.74%
Glucocorticoid receptor binding	+	0.7475	74.75%
Aromatase binding	+	0.6804	68.04%
PPAR gamma	+	0.8162	81.62%
Honey bee toxicity	-	0.6200	62.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8242	82.42%

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	98.46%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.37%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.77%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.59%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.05%	95.89%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.69%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.40%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	89.37%	94.75%
CHEMBL1914	P06276	Butyrylcholinesterase	88.91%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.86%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.81%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.73%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.85%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.51%	94.00%
CHEMBL1871	P10275	Androgen Receptor	85.55%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.41%	86.33%
CHEMBL4072	P07858	Cathepsin B	85.01%	93.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.43%	94.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.15%	96.00%
CHEMBL5028	O14672	ADAM10	82.67%	97.50%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.79%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.08%	93.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.04%	93.04%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.30%	95.50%

Plants that contains it

• Periploca sepium

Cross-Links

• PubChem: 101787404
• LOTUS: LTS0066985
• wikiData: Q104958853