[(2R,3R,4S,6S)-6-[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10-formyl-5,14-dihydroxy-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]phenanthren-3-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] acetate

Details

• Internal ID: 316e778f-e062-4c54-8312-25cea0020964
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(2R,3R,4S,6S)-6-[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10-formyl-5,14-dihydroxy-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]phenanthren-3-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-2-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)OC4CCC5(C6CCC7(C(CCC7(C6CCC5(C4)O)O)C8=CC(=O)OC8)C)C=O)C)CO)OC(=O)C)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@@H]([C@H]2O)O)O[C@H]3[C@@H](O[C@H]([C@@H]([C@@H]3O)O)O[C@H]4CC[C@@]5([C@H]6CC[C@@]7([C@H](CC[C@@]7([C@@H]6CC[C@@]5(C4)O)O)C8=CC(=O)OC8)C)C=O)C)CO)OC(=O)C)O
• InChI: InChI=1S/C43H64O19/c1-19-31(48)27(58-21(3)46)14-30(56-19)61-37-28(16-44)60-39(35(52)33(37)50)62-36-20(2)57-38(34(51)32(36)49)59-23-5-10-41(18-45)25-6-9-40(4)24(22-13-29(47)55-17-22)8-12-43(40,54)26(25)7-11-42(41,53)15-23/h13,18-20,23-28,30-39,44,48-54H,5-12,14-17H2,1-4H3/t19-,20+,23+,24-,25+,26-,27+,28-,30+,31-,32+,33-,34-,35-,36+,37-,38+,39+,40-,41+,42+,43+/m1/s1
• InChI Key: GRLPUQORKFXICV-FCRRALEQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₄O₁₉
• Molecular Weight: 885.00 g/mol
• Exact Mass: 884.40417981 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -0.97
• H-Bond Acceptor: 19
• 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	+	0.9004	90.04%
Caco-2	-	0.8841	88.41%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8695	86.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9047	90.47%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8713	87.13%
P-glycoprotein inhibitior	+	0.7376	73.76%
P-glycoprotein substrate	+	0.7494	74.94%
CYP3A4 substrate	+	0.7346	73.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8981	89.81%
CYP3A4 inhibition	-	0.7508	75.08%
CYP2C9 inhibition	-	0.9002	90.02%
CYP2C19 inhibition	-	0.9274	92.74%
CYP2D6 inhibition	-	0.9510	95.10%
CYP1A2 inhibition	-	0.9003	90.03%
CYP2C8 inhibition	+	0.6342	63.42%
CYP inhibitory promiscuity	-	0.9474	94.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5009	50.09%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9129	91.29%
Skin irritation	+	0.5321	53.21%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.5270	52.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8152	81.52%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7677	76.77%
skin sensitisation	-	0.9303	93.03%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8850	88.50%
Acute Oral Toxicity (c)	I	0.8814	88.14%
Estrogen receptor binding	+	0.8589	85.89%
Androgen receptor binding	+	0.7981	79.81%
Thyroid receptor binding	-	0.5806	58.06%
Glucocorticoid receptor binding	+	0.7123	71.23%
Aromatase binding	+	0.6972	69.72%
PPAR gamma	+	0.8024	80.24%
Honey bee toxicity	-	0.6183	61.83%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9694	96.94%

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	99.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.32%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.39%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	94.78%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.63%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.42%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.46%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.27%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.06%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.93%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.21%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.35%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	84.48%	91.19%
CHEMBL4208	P20618	Proteasome component C5	84.26%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.11%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.01%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.71%	95.50%
CHEMBL5028	O14672	ADAM10	81.40%	97.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.30%	92.62%

Plants that contains it

• Ornithogalum umbellatum

Cross-Links

• PubChem: 162930134
• LOTUS: LTS0146130
• wikiData: Q105016189