3-[(3S,5S,8S,9R,10S,13R,14R,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-10,13-dimethyl-15-oxo-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: a63e8d04-0240-4a0d-909e-a9bc2dc83a20
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8S,9R,10S,13R,14R,17R)-3-[(2R,4S,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-8,14-dihydroxy-10,13-dimethyl-15-oxo-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4(C3CCC5(C4(C(=O)CC5C6=CC(=O)OC6)O)C)O)C)O)OC7C(C(C(CO7)O)OC8C(C(CO8)(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@@]4([C@@H]3CC[C@]5([C@@]4(C(=O)C[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O[C@H]8[C@@H]([C@](CO8)(CO)O)O)O
• InChI: InChI=1S/C39H58O17/c1-18-30(55-33-29(45)31(24(42)15-51-33)56-34-32(46)37(47,16-40)17-52-34)23(41)13-28(53-18)54-21-5-7-35(2)20(11-21)4-9-38(48)25(35)6-8-36(3)22(12-26(43)39(36,38)49)19-10-27(44)50-14-19/h10,18,20-25,28-34,40-42,45-49H,4-9,11-17H2,1-3H3/t18-,20+,21+,22-,23+,24-,25-,28+,29-,30-,31+,32+,33+,34+,35+,36-,37-,38+,39-/m1/s1
• InChI Key: PBMGMUOWJPCPTN-DRXNMQTHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₈O₁₇
• Molecular Weight: 798.90 g/mol
• Exact Mass: 798.36740038 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -1.29
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8036	80.36%
Caco-2	-	0.8826	88.26%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8375	83.75%
OATP2B1 inhibitior	-	0.8751	87.51%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7945	79.45%
P-glycoprotein inhibitior	+	0.7253	72.53%
P-glycoprotein substrate	+	0.7982	79.82%
CYP3A4 substrate	+	0.7233	72.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
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	+	0.4885	48.85%
CYP inhibitory promiscuity	-	0.9425	94.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9159	91.59%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5208	52.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.8076	80.76%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9286	92.86%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5599	55.99%
Acute Oral Toxicity (c)	I	0.8759	87.59%
Estrogen receptor binding	+	0.7948	79.48%
Androgen receptor binding	+	0.7730	77.30%
Thyroid receptor binding	-	0.6055	60.55%
Glucocorticoid receptor binding	+	0.6509	65.09%
Aromatase binding	+	0.6691	66.91%
PPAR gamma	+	0.7205	72.05%
Honey bee toxicity	-	0.6438	64.38%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
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	98.21%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	96.79%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.88%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.80%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.52%	100.00%
CHEMBL2581	P07339	Cathepsin D	93.81%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.27%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.36%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.93%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.90%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	87.45%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.55%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.26%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.14%	90.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.05%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.65%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.95%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.68%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.62%	96.67%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.04%	96.90%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162874093
• LOTUS: LTS0252653
• wikiData: Q105205285