(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2S,4R,5S,6S)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid

Details

• Internal ID: 462fc115-228b-4458-8d77-d15756cee90f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2S,4R,5S,6S)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C(=O)O)OC)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)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]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C(=O)O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@@H]8[C@H]([C@@H]([C@H]([C@@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H64O20/c1-18-35(62-37-34(50)32(48)30(46)26(61-37)17-57-36-33(49)31(47)29(45)25(15-43)60-36)24(55-3)13-28(58-18)59-20-4-10-41(38(51)52)22-5-8-39(2)21(19-12-27(44)56-16-19)7-11-42(39,54)23(22)6-9-40(41,53)14-20/h12,18,20-26,28-37,43,45-50,53-54H,4-11,13-17H2,1-3H3,(H,51,52)/t18-,20-,21+,22-,23+,24+,25-,26+,28+,29-,30+,31+,32-,33-,34+,35-,36-,37-,39+,40-,41+,42-/m0/s1
• InChI Key: XBQOQVUCVQINTM-XEMFACPESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₂₀
• Molecular Weight: 888.90 g/mol
• Exact Mass: 888.39909443 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -2.03
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 11

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	-	0.8886	88.86%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8874	88.74%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8593	85.93%
P-glycoprotein inhibitior	+	0.7406	74.06%
P-glycoprotein substrate	+	0.7211	72.11%
CYP3A4 substrate	+	0.7333	73.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
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	+	0.5996	59.96%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9151	91.51%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6240	62.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.8104	81.04%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7602	76.02%
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	-	0.8574	85.74%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8572	85.72%
Androgen receptor binding	+	0.7842	78.42%
Thyroid receptor binding	-	0.6249	62.49%
Glucocorticoid receptor binding	+	0.7160	71.60%
Aromatase binding	+	0.7079	70.79%
PPAR gamma	+	0.7833	78.33%
Honey bee toxicity	-	0.6770	67.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.48%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.35%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.97%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.56%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.89%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.51%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	88.18%	92.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.73%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.84%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.72%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.70%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.30%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.79%	94.33%
CHEMBL2581	P07339	Cathepsin D	84.57%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	83.76%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.67%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.62%	97.36%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.41%	94.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.35%	81.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.15%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.08%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.99%	94.00%
CHEMBL1871	P10275	Androgen Receptor	80.18%	96.43%

Plants that contains it

• Strophanthus kombe

Cross-Links

• PubChem: 163101467
• LOTUS: LTS0252347
• wikiData: Q105324631