Wilfoside A

Details

• Internal ID: 96f5ce7d-59b9-4dc1-af8b-5e62266afc95
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: [(1S)-1-[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-12-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl] pyridine-3-carboxylate
• SMILES (Canonical): CC1C(C(CC(O1)OC2C(OC(CC2OC)OC3CCC4(C5CC(C6(C(CCC6(C5(CC=C4C3)O)O)(C(C)OC(=O)C7=CN=CC=C7)O)C)OC(=O)C=CC8=CC=CC=C8)C)C)OC)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@H]3CC[C@@]4([C@H]5C[C@H]([C@@]6([C@@](CC[C@@]6([C@@]5(CC=C4C3)O)O)([C@H](C)OC(=O)C7=CN=CC=C7)O)C)OC(=O)/C=C/C8=CC=CC=C8)C)C)OC)O
• InChI: InChI=1S/C50H67NO14/c1-29-43(53)36(58-6)25-42(60-29)65-44-30(2)61-41(26-37(44)59-7)63-35-18-19-46(4)34(24-35)17-20-49(56)38(46)27-39(64-40(52)16-15-32-12-9-8-10-13-32)47(5)48(55,21-22-50(47,49)57)31(3)62-45(54)33-14-11-23-51-28-33/h8-17,23,28-31,35-39,41-44,53,55-57H,18-22,24-27H2,1-7H3/b16-15+/t29-,30-,31+,35+,36-,37+,38-,39-,41+,42+,43-,44-,46+,47-,48-,49+,50-/m1/s1
• InChI Key: FLOMIRTZSBSGEW-NBXFTRSQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₆₇NO₁₄
• Molecular Weight: 906.10 g/mol
• Exact Mass: 905.45615581 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 5.22
• H-Bond Acceptor: 15
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8910	89.10%
Caco-2	-	0.8633	86.33%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5831	58.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8347	83.47%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8342	83.42%
BSEP inhibitior	+	0.9923	99.23%
P-glycoprotein inhibitior	+	0.7617	76.17%
P-glycoprotein substrate	+	0.7706	77.06%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.7933	79.33%
CYP2C9 inhibition	-	0.8783	87.83%
CYP2C19 inhibition	-	0.8750	87.50%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.6563	65.63%
CYP2C8 inhibition	+	0.8447	84.47%
CYP inhibitory promiscuity	-	0.8955	89.55%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4890	48.90%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9042	90.42%
Skin irritation	-	0.6647	66.47%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7823	78.23%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5185	51.85%
skin sensitisation	-	0.8554	85.54%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9686	96.86%
Acute Oral Toxicity (c)	II	0.3399	33.99%
Estrogen receptor binding	+	0.7836	78.36%
Androgen receptor binding	+	0.7607	76.07%
Thyroid receptor binding	+	0.6452	64.52%
Glucocorticoid receptor binding	+	0.7844	78.44%
Aromatase binding	+	0.5623	56.23%
PPAR gamma	+	0.7791	77.91%
Honey bee toxicity	-	0.6381	63.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5845	58.45%
Fish aquatic toxicity	+	0.9623	96.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.49%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.84%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95.42%	94.08%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.40%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	94.91%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	94.89%	91.07%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.86%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	93.65%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.86%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.25%	99.23%
CHEMBL2581	P07339	Cathepsin D	92.18%	98.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.96%	83.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.68%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.50%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	90.44%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.38%	85.14%
CHEMBL5028	O14672	ADAM10	89.83%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.47%	97.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.84%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.78%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.57%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.28%	95.56%
CHEMBL255	P29275	Adenosine A2b receptor	85.90%	98.59%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.88%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	83.34%	92.98%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.80%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.67%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.51%	89.67%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.09%	85.31%
CHEMBL1907599	P05556	Integrin alpha-4/beta-1	81.48%	92.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.88%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.29%	97.14%

Plants that contains it

• Cynanchum wilfordii
• Flemingia prostrata
• Mesembryanthemum tortuosum

Cross-Links

• PubChem: 102165348
• NPASS: NPC87232
• LOTUS: LTS0073563
• wikiData: Q104997295