[(3S,5R,10S,13R,14S,16S,17R)-3-[3,4-dihydroxy-6-methyl-5-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-14-hydroxy-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] propanoate

Details

• Internal ID: 690bcead-8c73-4b52-911e-c0eea0411416
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,10S,13R,14S,16S,17R)-3-[3,4-dihydroxy-6-methyl-5-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-14-hydroxy-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] propanoate
• SMILES (Canonical): CCC(=O)OC1CC2(C3CCC4CC(CCC4(C3CCC2(C1C5=CC(=O)OC5)C)C)OC6C(C(C(C(O6)C)OC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): CCC(=O)O[C@H]1C[C@@]2(C3CC[C@@H]4C[C@H](CC[C@@]4(C3CC[C@@]2([C@H]1C5=CC(=O)OC5)C)C)OC6C(C(C(C(O6)C)O[C@H]7[C@H](C([C@@H](C(O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C38H58O15/c1-5-25(40)51-23-14-38(47)22-7-6-19-13-20(8-10-36(19,3)21(22)9-11-37(38,4)27(23)18-12-26(41)48-16-18)50-34-32(46)30(44)33(17(2)49-34)53-35-31(45)29(43)28(42)24(15-39)52-35/h12,17,19-24,27-35,39,42-47H,5-11,13-16H2,1-4H3/t17?,19-,20+,21?,22?,23+,24?,27+,28-,29?,30?,31+,32?,33?,34?,35+,36+,37-,38+/m1/s1
• InChI Key: XRXCJPMZYAWJHD-JJGULWAKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₁₅
• Molecular Weight: 754.90 g/mol
• Exact Mass: 754.37757114 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.21
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8826	88.26%
Caco-2	-	0.8889	88.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8191	81.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7645	76.45%
P-glycoprotein inhibitior	+	0.7247	72.47%
P-glycoprotein substrate	+	0.7235	72.35%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.7083	70.83%
CYP2C9 inhibition	-	0.8785	87.85%
CYP2C19 inhibition	-	0.9085	90.85%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	-	0.9172	91.72%
CYP2C8 inhibition	+	0.5994	59.94%
CYP inhibitory promiscuity	-	0.9062	90.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5488	54.88%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9218	92.18%
Skin irritation	+	0.5231	52.31%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6093	60.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.7993	79.93%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6217	62.17%
skin sensitisation	-	0.9276	92.76%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8240	82.40%
Acute Oral Toxicity (c)	I	0.6857	68.57%
Estrogen receptor binding	+	0.8143	81.43%
Androgen receptor binding	+	0.7960	79.60%
Thyroid receptor binding	-	0.6933	69.33%
Glucocorticoid receptor binding	+	0.6295	62.95%
Aromatase binding	+	0.6798	67.98%
PPAR gamma	+	0.7356	73.56%
Honey bee toxicity	-	0.6219	62.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9747	97.47%

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	98.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.31%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.48%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.79%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.89%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.55%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.15%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	90.09%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.89%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.26%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.73%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.09%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.07%	96.21%
CHEMBL4208	P20618	Proteasome component C5	83.85%	90.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.81%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.58%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.29%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.85%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.71%	95.89%
CHEMBL1871	P10275	Androgen Receptor	81.38%	96.43%
CHEMBL2581	P07339	Cathepsin D	81.35%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.85%	96.77%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.39%	81.11%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.18%	85.83%

Plants that contains it

• Cryptostegia grandiflora

Cross-Links

• PubChem: 163030815
• LOTUS: LTS0116772
• wikiData: Q105340869