3beta-[(2,6-Dideoxy-3-O-methyl-4-O-beta-D-glucopyranosyl-beta-D-galactopyranosyl)oxy]-16beta-acetoxy-14-hydroxy-5beta,14beta-card-20(22)-enolide

Details

• Internal ID: 0f3c2850-4619-4a41-a0a8-68ab82a7957f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4R,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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-16-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)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](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C38H58O14/c1-18-34(52-35-33(44)32(43)31(42)27(16-39)51-35)25(46-5)14-29(48-18)50-22-8-10-36(3)21(13-22)6-7-24-23(36)9-11-37(4)30(20-12-28(41)47-17-20)26(49-19(2)40)15-38(24,37)45/h12,18,21-27,29-35,39,42-45H,6-11,13-17H2,1-5H3/t18-,21-,22+,23+,24-,25-,26+,27-,29+,30+,31-,32+,33-,34+,35+,36+,37-,38+/m1/s1
• InChI Key: ITYAEKHTQKSNBZ-YSVTVYQFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₁₄
• Molecular Weight: 738.90 g/mol
• Exact Mass: 738.38265652 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 8

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	-	0.8822	88.22%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	0.8733	87.33%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7613	76.13%
P-glycoprotein inhibitior	+	0.7396	73.96%
P-glycoprotein substrate	+	0.7652	76.52%
CYP3A4 substrate	+	0.7397	73.97%
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	+	0.5116	51.16%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9241	92.41%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6093	60.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.6584	65.84%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6842	68.42%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7965	79.65%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.7752	77.52%
Androgen receptor binding	+	0.8045	80.45%
Thyroid receptor binding	-	0.6775	67.75%
Glucocorticoid receptor binding	+	0.6639	66.39%
Aromatase binding	+	0.6821	68.21%
PPAR gamma	+	0.7225	72.25%
Honey bee toxicity	-	0.5856	58.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.60%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.55%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.96%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.93%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.44%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.95%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.69%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.46%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.21%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.44%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.11%	94.00%
CHEMBL2581	P07339	Cathepsin D	84.31%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.57%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.38%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.34%	90.00%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.86%	97.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.35%	96.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.76%	81.11%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 51351560
• NPASS: NPC43116
• LOTUS: LTS0213933
• wikiData: Q105120369