[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-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

Details

• Internal ID: 0821fd26-4a5f-4617-843f-20344c1bd89d
• 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,4S,5S,6R)-4-hydroxy-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)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](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)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C37H56O14/c1-17-33(51-34-32(44)31(43)30(42)26(15-38)50-34)24(40)13-28(47-17)49-21-7-9-35(3)20(12-21)5-6-23-22(35)8-10-36(4)29(19-11-27(41)46-16-19)25(48-18(2)39)14-37(23,36)45/h11,17,20-26,28-34,38,40,42-45H,5-10,12-16H2,1-4H3/t17-,20-,21+,22+,23-,24+,25+,26-,28+,29+,30-,31+,32-,33-,34+,35+,36-,37+/m1/s1
• InChI Key: YZMYUSLXATVAEH-DOYHUYMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₆O₁₄
• Molecular Weight: 724.80 g/mol
• Exact Mass: 724.36700646 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.85
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8861	88.61%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	0.8718	87.18%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6645	66.45%
P-glycoprotein inhibitior	+	0.7120	71.20%
P-glycoprotein substrate	+	0.7797	77.97%
CYP3A4 substrate	+	0.7296	72.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8550	85.50%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9340	93.40%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.4479	44.79%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9245	92.45%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5093	50.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.6846	68.46%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6217	62.17%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8022	80.22%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.8002	80.02%
Androgen receptor binding	+	0.8040	80.40%
Thyroid receptor binding	-	0.6965	69.65%
Glucocorticoid receptor binding	+	0.6450	64.50%
Aromatase binding	+	0.6896	68.96%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.6004	60.04%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9628	96.28%

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	98.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.33%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.17%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.30%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.61%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.78%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.65%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.84%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.01%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	86.18%	92.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.13%	81.11%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.03%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.12%	96.21%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.08%	97.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.63%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.55%	96.77%
CHEMBL4208	P20618	Proteasome component C5	82.51%	90.00%
CHEMBL5028	O14672	ADAM10	82.35%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.86%	95.89%
CHEMBL220	P22303	Acetylcholinesterase	81.56%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.89%	97.25%

Plants that contains it

• Cryptostegia grandiflora
• Streptocaulon juventas

Cross-Links

• PubChem: 101612261
• LOTUS: LTS0053775
• wikiData: Q105369338