(3R,5S,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-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: afbdf3f1-652b-4c66-b873-38de05425815
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3R,5S,10S,13R,14S,17R)-3-[(2R,5S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-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)O)O
• SMILES (Isomeric): CC1[C@H](C(C[C@@H](O1)O[C@@H]2CC[C@@]3(C4CC[C@@]5([C@H](CC[C@@]5(C4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C=O)O)O
• InChI: InChI=1S/C29H42O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h11,15-16,18-22,24-25,31,33-35H,3-10,12-14H2,1-2H3/t16?,18-,19-,20?,21?,22?,24+,25-,26-,27+,28+,29+/m1/s1
• InChI Key: QBILRDAMJUPXCX-DSIUHXAQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₂O₉
• Molecular Weight: 534.60 g/mol
• Exact Mass: 534.28288291 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9551	95.51%
Caco-2	-	0.8268	82.68%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8979	89.79%
OATP2B1 inhibitior	-	0.7272	72.72%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5607	56.07%
P-glycoprotein inhibitior	-	0.4626	46.26%
P-glycoprotein substrate	+	0.7811	78.11%
CYP3A4 substrate	+	0.6913	69.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8978	89.78%
CYP3A4 inhibition	-	0.8629	86.29%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9391	93.91%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.7266	72.66%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5164	51.64%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9455	94.55%
Skin irritation	+	0.5170	51.70%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.5870	58.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7884	78.84%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8018	80.18%
skin sensitisation	-	0.9082	90.82%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8136	81.36%
Acute Oral Toxicity (c)	I	0.8640	86.40%
Estrogen receptor binding	+	0.8273	82.73%
Androgen receptor binding	+	0.8168	81.68%
Thyroid receptor binding	-	0.5716	57.16%
Glucocorticoid receptor binding	+	0.6791	67.91%
Aromatase binding	+	0.6956	69.56%
PPAR gamma	-	0.5282	52.82%
Honey bee toxicity	-	0.7206	72.06%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9860	98.60%

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	97.29%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.37%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.29%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.03%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.02%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.18%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.05%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.52%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.75%	85.14%
CHEMBL4208	P20618	Proteasome component C5	88.68%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.14%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.66%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.02%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.51%	96.77%
CHEMBL2581	P07339	Cathepsin D	83.87%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.84%	97.14%
CHEMBL1871	P10275	Androgen Receptor	83.40%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.56%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.46%	90.24%

Plants that contains it

• Adonis mongolica
• Corchorus olitorius
• Draba nemorosa
• Erysimum cheiri
• Erysimum contractum
• Erysimum crepidifolium
• Erysimum leptophyllum
• Erysimum pulchellum

Cross-Links

• PubChem: 11967805
• LOTUS: LTS0238031
• wikiData: Q105217811