(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S,2S,4S,5'S,6R,7S,8R,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 79713b78-5071-41e5-90f4-1cf86dfe5bfc
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1S,2S,4S,5'S,6R,7S,8R,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C)C)OC17CCC(CO7)CO
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O[C@]17CC[C@H](CO7)CO
• InChI: InChI=1S/C33H52O9/c1-17-26-24(42-33(17)11-6-18(14-34)16-39-33)13-23-21-5-4-19-12-20(7-9-31(19,2)22(21)8-10-32(23,26)3)40-30-29(38)28(37)27(36)25(15-35)41-30/h4,17-18,20-30,34-38H,5-16H2,1-3H3/t17-,18-,20-,21+,22-,23-,24-,25+,26-,27+,28-,29+,30+,31-,32-,33+/m0/s1
• InChI Key: ZWGLNMGFGHSXND-REQRAIAKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₉
• Molecular Weight: 592.80 g/mol
• Exact Mass: 592.36113323 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7196	71.96%
Caco-2	-	0.8608	86.08%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7739	77.39%
OATP2B1 inhibitior	-	0.5788	57.88%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.8663	86.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6165	61.65%
P-glycoprotein inhibitior	+	0.6271	62.71%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7370	73.70%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9460	94.60%
CYP2C9 inhibition	-	0.9118	91.18%
CYP2C19 inhibition	-	0.9113	91.13%
CYP2D6 inhibition	-	0.9360	93.60%
CYP1A2 inhibition	-	0.8848	88.48%
CYP2C8 inhibition	+	0.7444	74.44%
CYP inhibitory promiscuity	-	0.8774	87.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5291	52.91%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9362	93.62%
Skin irritation	-	0.5662	56.62%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.8770	87.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7548	75.48%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.9226	92.26%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8013	80.13%
Acute Oral Toxicity (c)	III	0.4459	44.59%
Estrogen receptor binding	+	0.7179	71.79%
Androgen receptor binding	+	0.7001	70.01%
Thyroid receptor binding	-	0.6190	61.90%
Glucocorticoid receptor binding	+	0.5958	59.58%
Aromatase binding	+	0.6586	65.86%
PPAR gamma	+	0.5712	57.12%
Honey bee toxicity	-	0.6592	65.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9442	94.42%

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	98.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.85%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.66%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.03%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.45%	97.25%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.34%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.50%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.63%	95.89%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.47%	94.08%
CHEMBL2581	P07339	Cathepsin D	86.13%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.06%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.94%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.37%	94.45%
CHEMBL237	P41145	Kappa opioid receptor	82.54%	98.10%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.88%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.38%	93.56%
CHEMBL5028	O14672	ADAM10	81.27%	97.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.58%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.35%	94.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.00%	96.61%

Plants that contains it

• Lilium regale

Cross-Links

• PubChem: 162858990
• LOTUS: LTS0013124
• wikiData: Q105384927