(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2S,3R,4R,6R)-3-methoxy-6-methyl-4-[(2R,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: a232c301-2302-4cca-b27d-5db8cd109771
• 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,17R)-5,14-dihydroxy-3-[(2S,3R,4R,6R)-3-methoxy-6-methyl-4-[(2R,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): CC1CC(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)OC)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C36H54O14/c1-18-12-24(49-31-29(42)28(41)27(40)25(15-37)50-31)30(45-3)32(47-18)48-20-4-9-34(17-38)22-5-8-33(2)21(19-13-26(39)46-16-19)7-11-36(33,44)23(22)6-10-35(34,43)14-20/h13,17-18,20-25,27-32,37,40-44H,4-12,14-16H2,1-3H3/t18-,20+,21-,22+,23-,24-,25-,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+/m1/s1
• InChI Key: VTQWFYXLYNJGCR-OJSOPAHASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₄
• Molecular Weight: 710.80 g/mol
• Exact Mass: 710.35135639 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• BDBM50480586

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8830	88.30%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	0.8693	86.93%
OATP1B1 inhibitior	+	0.8938	89.38%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8542	85.42%
P-glycoprotein inhibitior	+	0.7086	70.86%
P-glycoprotein substrate	+	0.6644	66.44%
CYP3A4 substrate	+	0.7331	73.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8956	89.56%
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	+	0.6067	60.67%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9273	92.73%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7618	76.18%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6927	69.27%
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	-	0.8337	83.37%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8174	81.74%
Androgen receptor binding	+	0.8081	80.81%
Thyroid receptor binding	-	0.6402	64.02%
Glucocorticoid receptor binding	+	0.6442	64.42%
Aromatase binding	+	0.6806	68.06%
PPAR gamma	+	0.6635	66.35%
Honey bee toxicity	-	0.6462	64.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	98.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.84%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.60%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.15%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.35%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.35%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.32%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.71%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.06%	98.95%
CHEMBL1871	P10275	Androgen Receptor	87.98%	96.43%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.61%	96.00%
CHEMBL4208	P20618	Proteasome component C5	87.28%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.94%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.30%	92.94%
CHEMBL226	P30542	Adenosine A1 receptor	83.86%	95.93%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.78%	94.80%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.34%	90.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.83%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.23%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	82.19%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.55%	94.00%

Plants that contains it

• Ardisia gigantifolia
• Crossosoma bigelovii

Cross-Links

• PubChem: 44139361
• NPASS: NPC247190
• ChEMBL: CHEMBL553660
• LOTUS: LTS0219116
• wikiData: Q105216292