3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 555baf65-a8fd-4d11-a5de-5376256a7b20
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)CO)O)O)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)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](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C41H64O19/c1-17-34(59-38-33(52)30(49)35(25(14-43)58-38)60-37-31(50)28(47)27(46)24(13-42)57-37)29(48)32(51)36(55-17)56-20-5-9-40(16-44)19(12-20)3-4-23-22(40)6-8-39(2)21(7-10-41(23,39)53)18-11-26(45)54-15-18/h11,17,19-25,27-38,42-44,46-53H,3-10,12-16H2,1-2H3/t17-,19+,20+,21-,22+,23-,24-,25-,27-,28+,29+,30-,31-,32-,33-,34-,35-,36+,37+,38+,39-,40-,41+/m1/s1
• InChI Key: WQDHYVJFORMDEQ-BXBFFZSYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₉
• Molecular Weight: 860.90 g/mol
• Exact Mass: 860.40417981 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -2.92
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8248	82.48%
Caco-2	-	0.8974	89.74%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7845	78.45%
P-glycoprotein inhibitior	+	0.7159	71.59%
P-glycoprotein substrate	+	0.6483	64.83%
CYP3A4 substrate	+	0.7177	71.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.9242	92.42%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4844	48.44%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.6324	63.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8821	88.21%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8324	83.24%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.8561	85.61%
Androgen receptor binding	+	0.8176	81.76%
Thyroid receptor binding	-	0.6599	65.99%
Glucocorticoid receptor binding	+	0.6152	61.52%
Aromatase binding	+	0.7222	72.22%
PPAR gamma	+	0.7546	75.46%
Honey bee toxicity	-	0.6229	62.29%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9498	94.98%

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	99.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.64%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.79%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.14%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.94%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.06%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.65%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.17%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.53%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	88.06%	81.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.86%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.65%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.97%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	86.49%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.02%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.81%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.46%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.97%	95.93%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.06%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.04%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.81%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.36%	96.21%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 10373405
• NPASS: NPC44243
• LOTUS: LTS0182698
• wikiData: Q105310455