Hellebrigenin 3-O-glucosylrhamnoside

Details

• Internal ID: 51c0645a-7bee-4f20-8e9e-b08de32036b3
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: (3S,5S,9S,10S,13R,14S,17R)-3-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=COC(=O)C=C6)C)C=O)O)O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5(C4CC[C@@]3(C2)O)O)C6=COC(=O)C=C6)C)C=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C36H52O15/c1-17-30(51-32-28(43)26(41)25(40)23(14-37)50-32)27(42)29(44)31(48-17)49-19-5-10-34(16-38)21-6-9-33(2)20(18-3-4-24(39)47-15-18)8-12-36(33,46)22(21)7-11-35(34,45)13-19/h3-4,15-17,19-23,25-32,37,40-46H,5-14H2,1-2H3/t17-,19-,20+,21-,22?,23+,25+,26-,27-,28+,29+,30-,31-,32-,33+,34-,35-,36-/m0/s1
• InChI Key: DCSLTSSPIJWEJN-UVOXVOIDSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₂O₁₅
• Molecular Weight: 724.80 g/mol
• Exact Mass: 724.33062095 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -0.79
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Hellebrigenin 3-O-glucosylrhamnoside
• 3beta-(6-deoxy-4-O-beta-D-glucopyranosyl-alpha-L-mannopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta-bufa-20,22-dienolide
• (3S,5S,9S,10S,13R,14S,17R)-3-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 3-[3,4-dihydroxy-6-methyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 13289-18-4
• SCHEMBL868838
• CHEBI:28271
• LMST01130006

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7682	76.82%
Caco-2	-	0.8865	88.65%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7971	79.71%
OATP2B1 inhibitior	-	0.8682	86.82%
OATP1B1 inhibitior	+	0.8559	85.59%
OATP1B3 inhibitior	+	0.9198	91.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.7169	71.69%
P-glycoprotein inhibitior	+	0.6955	69.55%
P-glycoprotein substrate	-	0.5892	58.92%
CYP3A4 substrate	+	0.7151	71.51%
CYP2C9 substrate	-	0.8043	80.43%
CYP2D6 substrate	-	0.8628	86.28%
CYP3A4 inhibition	-	0.7144	71.44%
CYP2C9 inhibition	-	0.9220	92.20%
CYP2C19 inhibition	-	0.9270	92.70%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.8764	87.64%
CYP2C8 inhibition	+	0.6183	61.83%
CYP inhibitory promiscuity	-	0.9430	94.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6788	67.88%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9229	92.29%
Skin irritation	-	0.7002	70.02%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7898	78.98%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7104	71.04%
skin sensitisation	-	0.9382	93.82%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8096	80.96%
Acute Oral Toxicity (c)	I	0.5727	57.27%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	+	0.7577	75.77%
Thyroid receptor binding	-	0.5770	57.70%
Glucocorticoid receptor binding	+	0.6363	63.63%
Aromatase binding	+	0.6582	65.82%
PPAR gamma	+	0.6853	68.53%
Honey bee toxicity	-	0.7295	72.95%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9700	97.00%

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	98.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.82%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.99%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.93%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.41%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.72%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.97%	89.00%
CHEMBL4208	P20618	Proteasome component C5	89.22%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.10%	95.93%
CHEMBL2581	P07339	Cathepsin D	88.80%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.55%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.32%	86.92%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.87%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.59%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.77%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.53%	97.25%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.30%	89.44%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.52%	97.36%
CHEMBL3524	P56524	Histone deacetylase 4	81.05%	92.97%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.10%	89.67%

Plants that contains it

• Caltha palustris
• Helleborus niger

Cross-Links

• PubChem: 10439890
• NPASS: NPC150817