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

Details

• Internal ID: 8c9bdf41-09f5-41c1-86fe-f285a70862d2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4R,6R)-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H](C[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)C)OC(=O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C43H66O18/c1-19-38(61-40-37(52)35(50)33(48)29(60-40)18-55-39-36(51)34(49)32(47)28(16-44)59-39)27(57-20(2)45)15-31(56-19)58-23-7-10-41(3)22(14-23)5-6-26-25(41)8-11-42(4)24(9-12-43(26,42)53)21-13-30(46)54-17-21/h13,19,22-29,31-40,44,47-53H,5-12,14-18H2,1-4H3/t19-,22-,23+,24-,25+,26-,27-,28-,29-,31+,32-,33-,34+,35+,36-,37-,38-,39-,40+,41+,42-,43+/m1/s1
• InChI Key: QMFIJGFTYUHBOS-ABSSGRENSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₆O₁₈
• Molecular Weight: 871.00 g/mol
• Exact Mass: 870.42491525 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.30
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8939	89.39%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9154	91.54%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9159	91.59%
P-glycoprotein inhibitior	+	0.7418	74.18%
P-glycoprotein substrate	+	0.7803	78.03%
CYP3A4 substrate	+	0.7326	73.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8550	85.50%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.4688	46.88%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9207	92.07%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8097	80.97%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8113	81.13%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8700	87.00%
Androgen receptor binding	+	0.8010	80.10%
Thyroid receptor binding	-	0.6370	63.70%
Glucocorticoid receptor binding	+	0.7049	70.49%
Aromatase binding	+	0.6983	69.83%
PPAR gamma	+	0.8093	80.93%
Honey bee toxicity	-	0.6158	61.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9628	96.28%

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	99.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.85%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.57%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.74%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.23%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.71%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.85%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.30%	81.11%
CHEMBL2581	P07339	Cathepsin D	89.22%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.93%	85.14%
CHEMBL5255	O00206	Toll-like receptor 4	88.14%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.91%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.67%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.52%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.33%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.24%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.87%	95.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.52%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.25%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.11%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.74%	94.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.21%	96.00%
CHEMBL1871	P10275	Androgen Receptor	82.16%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.13%	99.23%
CHEMBL5028	O14672	ADAM10	82.12%	97.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.59%	96.21%

Plants that contains it

• Streptocaulon juventas

Cross-Links

• PubChem: 44566914
• NPASS: NPC474908
• ChEMBL: CHEMBL487262