3-[(3S,5R,8R,9S,10S,13R,14R,17S)-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13,14-trimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 67f6b417-a6c2-457d-b2eb-9adbbb495ba2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,13R,14R,17S)-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13,14-trimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)C)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(CC[C@@H]5C6=CC(=O)OC6)C)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C37H58O11/c1-19-33(48-34-32(42)31(41)30(40)27(17-38)47-34)26(43-5)16-29(45-19)46-22-8-11-35(2)21(15-22)6-7-25-24(35)10-13-36(3)23(9-12-37(25,36)4)20-14-28(39)44-18-20/h14,19,21-27,29-34,38,40-42H,6-13,15-18H2,1-5H3/t19-,21-,22+,23-,24+,25-,26+,27-,29+,30-,31+,32-,33-,34+,35+,36-,37-/m1/s1
• InChI Key: LMZSCLAHNSQLBW-KKGVSKAOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₈O₁₁
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.39791266 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7824	78.24%
Caco-2	-	0.8716	87.16%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8165	81.65%
OATP2B1 inhibitior	-	0.7368	73.68%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7310	73.10%
P-glycoprotein inhibitior	+	0.7391	73.91%
P-glycoprotein substrate	+	0.7133	71.33%
CYP3A4 substrate	+	0.7201	72.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8969	89.69%
CYP3A4 inhibition	-	0.9546	95.46%
CYP2C9 inhibition	-	0.9099	90.99%
CYP2C19 inhibition	-	0.9043	90.43%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	-	0.6847	68.47%
CYP inhibitory promiscuity	-	0.8806	88.06%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5961	59.61%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9289	92.89%
Skin irritation	-	0.6193	61.93%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7807	78.07%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9188	91.88%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7783	77.83%
Acute Oral Toxicity (c)	I	0.7506	75.06%
Estrogen receptor binding	+	0.7497	74.97%
Androgen receptor binding	+	0.8215	82.15%
Thyroid receptor binding	-	0.6904	69.04%
Glucocorticoid receptor binding	+	0.6170	61.70%
Aromatase binding	+	0.7112	71.12%
PPAR gamma	+	0.6551	65.51%
Honey bee toxicity	-	0.6179	61.79%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9347	93.47%

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	98.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.53%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.28%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.07%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.89%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.12%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.85%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.02%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.71%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.19%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.80%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.30%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.63%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.54%	96.21%
CHEMBL1871	P10275	Androgen Receptor	82.80%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.23%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	81.31%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.12%	97.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.20%	96.00%

Plants that contains it

• Periploca sepium

Cross-Links

• PubChem: 163046906
• LOTUS: LTS0262471
• wikiData: Q105154217