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

Details

• Internal ID: d83c71e1-1cdc-4373-a352-af567d744aae
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5R,8R,9S,10R,13R,14S,17R)-3-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C=O)OC)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)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](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C=O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C42H64O18/c1-19-36(59-39-35(51)33(49)37(28(16-44)58-39)60-38-34(50)32(48)31(47)27(15-43)57-38)26(53-3)14-30(55-19)56-22-6-10-41(18-45)21(13-22)4-5-25-24(41)7-9-40(2)23(8-11-42(25,40)52)20-12-29(46)54-17-20/h12,18-19,21-28,30-39,43-44,47-52H,4-11,13-17H2,1-3H3/t19-,21-,22+,23-,24+,25-,26-,27-,28-,30+,31-,32+,33-,34-,35-,36-,37-,38+,39+,40-,41-,42+/m1/s1
• InChI Key: SETOMNSAVMFIPE-PFYUGPJESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₁₈
• Molecular Weight: 856.90 g/mol
• Exact Mass: 856.40926519 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• 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	-	0.8927	89.27%
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	+	0.9058	90.58%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9611	96.11%
P-glycoprotein inhibitior	+	0.7399	73.99%
P-glycoprotein substrate	+	0.7623	76.23%
CYP3A4 substrate	+	0.7296	72.96%
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	+	0.5387	53.87%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9223	92.23%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5624	56.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8383	83.83%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7015	70.15%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8487	84.87%
Androgen receptor binding	+	0.8225	82.25%
Thyroid receptor binding	-	0.6431	64.31%
Glucocorticoid receptor binding	+	0.6830	68.30%
Aromatase binding	+	0.6935	69.35%
PPAR gamma	+	0.7655	76.55%
Honey bee toxicity	-	0.6094	60.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	98.64%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.82%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.55%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.40%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.38%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.20%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.02%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.19%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.14%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.15%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.88%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.04%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.89%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.43%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.05%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.54%	97.33%
CHEMBL4208	P20618	Proteasome component C5	83.48%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.70%	97.36%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.24%	97.14%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.48%	92.86%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.32%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.78%	89.00%

Plants that contains it

• Apocynum cannabinum

Cross-Links

• PubChem: 10328219
• LOTUS: LTS0179821
• wikiData: Q105251491