Scilliroside

Details

• Internal ID: bde1b846-b4f1-4ca6-a70b-c2f0d03df67c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: [(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• InChI: InChI=1S/C32H44O12/c1-16(34)42-21-13-31(39)23(8-10-30(3)19(7-11-32(30,31)40)17-4-5-24(35)41-15-17)29(2)9-6-18(12-20(21)29)43-28-27(38)26(37)25(36)22(14-33)44-28/h4-5,12,15,18-19,21-23,25-28,33,36-40H,6-11,13-14H2,1-3H3/t18-,19+,21+,22+,23+,25+,26-,27+,28+,29-,30+,31-,32+/m0/s1
• InChI Key: LSMIOFMZNVEEBR-ICLSSMQGSA-N
• Popularity: 50 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₁₂
• Molecular Weight: 620.70 g/mol
• Exact Mass: 620.28327683 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.64
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Scillirosan
• Silmurin
• Scillirosid
• Silmine
• 507-60-8
• 2815004NHO
• Scillirosidin + glucose
• NSC 7523
• Red Squill
• (3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)-3-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-6-yl acetate
• Caswell No. 722
• Squill
• NSC-7523
• Scilliroside, (3beta,6beta)-
• UNII-2815004NHO
• Scillirosidin + glucose [German]
• Bufa-4,20,22-trienolide, 6-(acetyloxy)-3-(.beta.-D-glucopyranosyloxy)-8,14-dihydroxy-, (3.beta.,6.beta.)-
• EINECS 208-077-4
• EPA Pesticide Chemical Code 070801
• BRN 0074900
• SCILLIROSIDE [MI]
• (3-beta,6-beta)scilliroside
• 4-18-00-03178 (Beilstein Handbook Reference)
• SCHEMBL433422
• DTXSID5042374
• HSDB 6733
• Scilliroside, (3-beta,6-beta)-
• 6-beta-(Acetyloxy)-3-beta-(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• 6beta-Acetoxy-3beta(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• Bufa-4,20,22-trienolide, 6-(acetyloxy)-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxy-
• [(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• 3-beta,6-beta-6-Acetyloxy-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• Bufa-4,20,22-trienolide, 6-(acetyloxy)-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxy-, (3beta,6beta)-
• C08880
• Q7433895
• 6beta-(Acetyloxy)-3-beta-(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• (3beta,6beta)-6-(Acetyloxy)-3-(beta-D-glucopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• [(3S,6R,8S,9R,10R,13R,14R,17R)-8,14-dihydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,3,6,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
• 3-beta,6-beta-6-acetyloxy-3-(beta-d-glocopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide
• 3beta-(beta-D-Glucopyropyanosyloxy)-6beta,8,14-trihydroxybufa-4,20,22-trienolide 6-accetate
• 6-beta-6-(acetyloxy)-3-beta-(beta-d-glocopyranosyloxy)-8,14-dihydroxybufa-4,20,22-trienolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9170	91.70%
Caco-2	-	0.9023	90.23%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	0.7261	72.61%
OATP1B1 inhibitior	+	0.7975	79.75%
OATP1B3 inhibitior	+	0.8633	86.33%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8276	82.76%
BSEP inhibitior	+	0.8647	86.47%
P-glycoprotein inhibitior	+	0.6657	66.57%
P-glycoprotein substrate	-	0.5929	59.29%
CYP3A4 substrate	+	0.7213	72.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.7112	71.12%
CYP2C9 inhibition	-	0.8844	88.44%
CYP2C19 inhibition	-	0.9255	92.55%
CYP2D6 inhibition	-	0.9365	93.65%
CYP1A2 inhibition	-	0.8717	87.17%
CYP2C8 inhibition	+	0.6450	64.50%
CYP inhibitory promiscuity	-	0.8888	88.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5817	58.17%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9300	93.00%
Skin irritation	-	0.5531	55.31%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7963	79.63%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6748	67.48%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7107	71.07%
Acute Oral Toxicity (c)	I	0.7810	78.10%
Estrogen receptor binding	+	0.8352	83.52%
Androgen receptor binding	+	0.7294	72.94%
Thyroid receptor binding	-	0.5640	56.40%
Glucocorticoid receptor binding	+	0.7068	70.68%
Aromatase binding	+	0.6826	68.26%
PPAR gamma	+	0.6269	62.69%
Honey bee toxicity	-	0.7259	72.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9905	99.05%

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	98.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.61%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.27%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.80%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.84%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.34%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.23%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.00%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.37%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.81%	94.00%
CHEMBL4208	P20618	Proteasome component C5	86.44%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.22%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.12%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.23%	89.67%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.90%	89.44%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.51%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	80.31%	95.93%

Plants that contains it

• Drimia maritima

Cross-Links

• PubChem: 441871
• LOTUS: LTS0047972
• wikiData: Q7433895