[(2S,3S,4S,5S,6S)-2-[[(3S,5R,8S,9R,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]-4-methoxy-6-methyl-5-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-3-yl] acetate

Details

• Internal ID: ac1ceba7-b2c5-451c-abbc-a829e902638f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2S,3S,4S,5S,6S)-2-[[(3S,5R,8S,9R,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]-4-methoxy-6-methyl-5-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)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@@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)C)OC(=O)C)OC)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/C44H68O19/c1-19-36(63-40-35(53)33(51)31(49)28(62-40)18-57-39-34(52)32(50)30(48)27(16-45)61-39)37(55-5)38(59-20(2)46)41(58-19)60-23-8-11-42(3)22(15-23)6-7-26-25(42)9-12-43(4)24(10-13-44(26,43)54)21-14-29(47)56-17-21/h14,19,22-28,30-41,45,48-54H,6-13,15-18H2,1-5H3/t19-,22+,23-,24+,25+,26-,27-,28-,30+,31+,32-,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43+,44-/m0/s1
• InChI Key: ILSCMGXPNCDKNU-FIKQGBROSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₈O₁₉
• Molecular Weight: 901.00 g/mol
• Exact Mass: 900.43547994 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.67
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8918	89.18%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9093	90.93%
P-glycoprotein inhibitior	+	0.7492	74.92%
P-glycoprotein substrate	+	0.7449	74.49%
CYP3A4 substrate	+	0.7380	73.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
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	+	0.5700	57.00%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7947	79.47%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7250	72.50%
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	-	0.7829	78.29%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8561	85.61%
Androgen receptor binding	+	0.7979	79.79%
Thyroid receptor binding	-	0.6128	61.28%
Glucocorticoid receptor binding	+	0.7244	72.44%
Aromatase binding	+	0.6818	68.18%
PPAR gamma	+	0.8092	80.92%
Honey bee toxicity	-	0.6113	61.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	99.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.51%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.17%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.84%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.67%	94.45%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	95.33%	81.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.15%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.67%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.65%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.40%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.02%	94.75%
CHEMBL5255	O00206	Toll-like receptor 4	89.71%	92.50%
CHEMBL2581	P07339	Cathepsin D	88.90%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.77%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	88.50%	95.93%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.43%	93.04%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.32%	97.36%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.08%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.66%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.49%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.07%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.75%	82.69%
CHEMBL1871	P10275	Androgen Receptor	84.40%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.27%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.01%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.51%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.80%	99.23%
CHEMBL5028	O14672	ADAM10	80.68%	97.50%

Plants that contains it

• Cerbera manghas

Cross-Links

• PubChem: 162994973
• LOTUS: LTS0173957
• wikiData: Q105115436