(3S,5S,8S,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-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: 99a097a8-1e7b-44d4-9de8-9f0bf353524c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5S,8S,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-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(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)OC)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)OC)O
• InChI: InChI=1S/C30H44O9/c1-17-26(33)23(36-3)13-25(38-17)39-19-4-9-28(16-31)21-5-8-27(2)20(18-12-24(32)37-15-18)7-11-30(27,35)22(21)6-10-29(28,34)14-19/h12,16-17,19-23,25-26,33-35H,4-11,13-15H2,1-3H3/t17-,19+,20-,21+,22+,23-,25+,26+,27-,28+,29+,30+/m1/s1
• InChI Key: XQCGNURMLWFQJR-NGLNAUAZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₉
• Molecular Weight: 548.70 g/mol
• Exact Mass: 548.29853298 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.8138	81.38%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8454	84.54%
OATP2B1 inhibitior	-	0.5885	58.85%
OATP1B1 inhibitior	+	0.9311	93.11%
OATP1B3 inhibitior	+	0.9726	97.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.8868	88.68%
P-glycoprotein inhibitior	+	0.6368	63.68%
P-glycoprotein substrate	+	0.7713	77.13%
CYP3A4 substrate	+	0.7111	71.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8989	89.89%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9087	90.87%
CYP2C8 inhibition	-	0.6194	61.94%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4628	46.28%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9394	93.94%
Skin irritation	+	0.4943	49.43%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7012	70.12%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7893	78.93%
skin sensitisation	-	0.9150	91.50%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7962	79.62%
Acute Oral Toxicity (c)	I	0.8422	84.22%
Estrogen receptor binding	+	0.7909	79.09%
Androgen receptor binding	+	0.8119	81.19%
Thyroid receptor binding	-	0.5639	56.39%
Glucocorticoid receptor binding	+	0.7286	72.86%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	-	0.4843	48.43%
Honey bee toxicity	-	0.6773	67.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9692	96.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	100 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	501.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.40%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.27%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.98%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.56%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.32%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.88%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.06%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	88.51%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.46%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.44%	92.94%
CHEMBL4208	P20618	Proteasome component C5	87.06%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.04%	97.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.91%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.63%	85.14%
CHEMBL1871	P10275	Androgen Receptor	86.15%	96.43%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.53%	90.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.57%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.38%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.49%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.80%	82.69%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.45%	93.40%

Plants that contains it

• Strophanthus kombe

Cross-Links

• PubChem: 163005123
• LOTUS: LTS0205507
• wikiData: Q105339475