(3S,5S,8R,9S,10S,13R,14S,16S,17R)-5,14,16-trihydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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]phenanthrene-10-carbaldehyde

Details

• Internal ID: 72693670-ef8f-4e5a-821c-a7dcff2e0cfa
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14S,16S,17R)-5,14,16-trihydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(C(CC5(C4CCC3(C2)O)O)O)C6=CC(=O)OC6)C)C=O)O)OC7C(C(C(C(O7)CO)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]4CC[C@@]5([C@H]([C@H](C[C@@]5([C@@H]4CC[C@@]3(C2)O)O)O)C6=CC(=O)OC6)C)C=O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C35H52O15/c1-16-30(50-31-29(43)28(42)27(41)23(13-36)49-31)21(38)10-25(47-16)48-18-3-7-33(15-37)19-4-6-32(2)26(17-9-24(40)46-14-17)22(39)12-35(32,45)20(19)5-8-34(33,44)11-18/h9,15-16,18-23,25-31,36,38-39,41-45H,3-8,10-14H2,1-2H3/t16-,18+,19+,20-,21+,22+,23-,25+,26+,27-,28+,29-,30+,31+,32-,33+,34+,35+/m1/s1
• InChI Key: PLMWECYQRHDXMP-PAHUVANNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₂O₁₅
• Molecular Weight: 712.80 g/mol
• Exact Mass: 712.33062095 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7963	79.63%
Caco-2	-	0.8860	88.60%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8579	85.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6815	68.15%
P-glycoprotein inhibitior	+	0.6793	67.93%
P-glycoprotein substrate	+	0.6918	69.18%
CYP3A4 substrate	+	0.7202	72.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8962	89.62%
CYP3A4 inhibition	-	0.8731	87.31%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.9341	93.41%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.9128	91.28%
CYP2C8 inhibition	+	0.5157	51.57%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9218	92.18%
Skin irritation	-	0.5515	55.15%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5407	54.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.7695	76.95%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6052	60.52%
skin sensitisation	-	0.9252	92.52%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8285	82.85%
Acute Oral Toxicity (c)	I	0.8538	85.38%
Estrogen receptor binding	+	0.8210	82.10%
Androgen receptor binding	+	0.8007	80.07%
Thyroid receptor binding	-	0.6270	62.70%
Glucocorticoid receptor binding	+	0.6119	61.19%
Aromatase binding	+	0.6692	66.92%
PPAR gamma	+	0.6658	66.58%
Honey bee toxicity	-	0.6545	65.45%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9644	96.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.78%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.27%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.04%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.49%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.81%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.40%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.03%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.22%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	88.73%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.63%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.26%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.04%	96.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.70%	96.00%
CHEMBL1871	P10275	Androgen Receptor	81.52%	96.43%

Plants that contains it

• Erysimum cheiranthoides

Cross-Links

• PubChem: 101689886
• LOTUS: LTS0145312
• wikiData: Q105211041