Alepposide B

Details

• Internal ID: a87c0a33-2879-4ebf-80ab-7c06b1c4321c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-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(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)OC)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3(C4CC[C@@]5([C@H](CC[C@@]5(C4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC)O
• InChI: InChI=1S/C48H74O20/c1-22-41(66-36-16-31(52)42(23(2)62-36)67-37-17-32(59-5)43(24(3)63-37)68-44-40(56)39(55)38(54)33(19-49)65-44)30(51)15-35(61-22)64-26-6-11-46(21-50)28-7-10-45(4)27(25-14-34(53)60-20-25)9-13-48(45,58)29(28)8-12-47(46,57)18-26/h14,21-24,26-33,35-44,49,51-52,54-58H,6-13,15-20H2,1-5H3/t22-,23-,24-,26+,27-,28?,29?,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45-,46+,47+,48+/m1/s1
• InChI Key: IMNHFZIFCBHSQR-GTRACWGGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₂₀
• Molecular Weight: 971.10 g/mol
• Exact Mass: 970.47734475 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 20
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• Alepposide-B
• 146714-04-7
• Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-O-2,6-dideoxy-3-O-methyl-beta-D-arabino-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5beta)-
• Strophanthidin-3-O-glucopyranosyl-(1-4)-O-beta-oleandropyranosyl-(1-4)-O-beta-digitoxopyranosyl-(1-4)-O-beta-digitoxopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8783	87.83%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9026	90.26%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9481	94.81%
P-glycoprotein inhibitior	+	0.7442	74.42%
P-glycoprotein substrate	+	0.7689	76.89%
CYP3A4 substrate	+	0.7286	72.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8956	89.56%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.5339	53.39%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9086	90.86%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.5230	52.30%
Human Ether-a-go-go-Related Gene inhibition	+	0.8282	82.82%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7052	70.52%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8698	86.98%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8690	86.90%
Androgen receptor binding	+	0.8108	81.08%
Thyroid receptor binding	-	0.5165	51.65%
Glucocorticoid receptor binding	+	0.7694	76.94%
Aromatase binding	+	0.6964	69.64%
PPAR gamma	+	0.8284	82.84%
Honey bee toxicity	-	0.6278	62.78%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	99.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.93%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.37%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.80%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.42%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.50%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	89.48%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.03%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.09%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.21%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.91%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.74%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.90%	97.14%
CHEMBL1871	P10275	Androgen Receptor	83.63%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.08%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.03%	97.36%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.90%	91.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.80%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.62%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.03%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.92%	97.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.17%	92.62%

Plants that contains it

• Adonis aleppica

Cross-Links

• PubChem: 132427638
• LOTUS: LTS0180861
• wikiData: Q105115785