(3S,5S,8R,9S,10S,13R,14S,16S,17S)-5,14,16-trihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-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-carbaldehyde

Details

• Internal ID: 4df1ff66-4276-409b-a641-3f358d0b1de8
• 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,16S,17S)-5,14,16-trihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-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-carbaldehyde
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(C(CC5(C4CCC3(C2)O)O)O)C6=CC(=O)OC6)C)C=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]([C@H](C[C@@]5([C@@H]4CC[C@@]3(C2)O)O)O)C6=CC(=O)OC6)C)C=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/c1-18-36(62-38-35(52)33(50)31(48)26(61-38)16-57-37-34(51)32(49)30(47)25(14-43)60-37)24(55-3)11-28(58-18)59-20-4-8-40(17-44)21-5-7-39(2)29(19-10-27(46)56-15-19)23(45)13-42(39,54)22(21)6-9-41(40,53)12-20/h10,17-18,20-26,28-38,43,45,47-54H,4-9,11-16H2,1-3H3/t18-,20+,21+,22-,23+,24+,25-,26-,28+,29-,30-,31-,32+,33+,34-,35-,36-,37-,38+,39-,40+,41+,42+/m1/s1
• InChI Key: BJRXMZMULNHQIY-HVHNJPGXSA-N
• Popularity: 1 reference 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: -3.90
• Atomic LogP (AlogP): -2.95
• H-Bond Acceptor: 20
• 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	-	0.8869	88.69%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8790	87.90%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9594	95.94%
P-glycoprotein inhibitior	+	0.7410	74.10%
P-glycoprotein substrate	+	0.7424	74.24%
CYP3A4 substrate	+	0.7393	73.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8956	89.56%
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	+	0.6337	63.37%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9142	91.42%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5393	53.93%
Human Ether-a-go-go-Related Gene inhibition	+	0.8118	81.18%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6552	65.52%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7996	79.96%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8578	85.78%
Androgen receptor binding	+	0.7862	78.62%
Thyroid receptor binding	-	0.5931	59.31%
Glucocorticoid receptor binding	+	0.7189	71.89%
Aromatase binding	+	0.6831	68.31%
PPAR gamma	+	0.7891	78.91%
Honey bee toxicity	-	0.6311	63.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.21%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.42%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.34%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.87%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.19%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.10%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.26%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	92.77%	95.93%
CHEMBL1871	P10275	Androgen Receptor	91.87%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.94%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.93%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.36%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.61%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.93%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.24%	97.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.23%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.06%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.98%	96.90%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.35%	94.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.21%	97.14%
CHEMBL5957	P21589	5'-nucleotidase	80.45%	97.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.18%	94.00%

Plants that contains it

• Strophanthus kombe

Cross-Links

• PubChem: 162899680
• LOTUS: LTS0246150
• wikiData: Q104937333