12beta,14,19-Trihydroxy-3beta-(6-deoxy-beta-D-allopyranosyloxy)-5alpha-card-20(22)-enolide

Details

• Internal ID: c7f2f1e8-b9b6-4c9b-bbfc-079ea760e291
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-12,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)CO)O)O)O
• InChI: InChI=1S/C29H44O10/c1-14-23(33)24(34)25(35)26(38-14)39-17-5-7-28(13-30)16(10-17)3-4-19-20(28)11-21(31)27(2)18(6-8-29(19,27)36)15-9-22(32)37-12-15/h9,14,16-21,23-26,30-31,33-36H,3-8,10-13H2,1-2H3/t14-,16+,17+,18-,19-,20+,21-,23-,24-,25-,26+,27+,28-,29+/m1/s1
• InChI Key: XKSBWDXNRFPBGG-KEJJPQHHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₀
• Molecular Weight: 552.70 g/mol
• Exact Mass: 552.29344760 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7905	79.05%
Caco-2	-	0.8591	85.91%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8521	85.21%
OATP2B1 inhibitior	-	0.7467	74.67%
OATP1B1 inhibitior	+	0.9359	93.59%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5696	56.96%
P-glycoprotein inhibitior	-	0.5319	53.19%
P-glycoprotein substrate	+	0.7415	74.15%
CYP3A4 substrate	+	0.6692	66.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9516	95.16%
CYP2C9 inhibition	-	0.9310	93.10%
CYP2C19 inhibition	-	0.9254	92.54%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.9043	90.43%
CYP2C8 inhibition	-	0.7746	77.46%
CYP inhibitory promiscuity	-	0.9136	91.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6262	62.62%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9449	94.49%
Skin irritation	-	0.6105	61.05%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.5579	55.79%
Human Ether-a-go-go-Related Gene inhibition	+	0.8849	88.49%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9048	90.48%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6808	68.08%
Acute Oral Toxicity (c)	I	0.7772	77.72%
Estrogen receptor binding	+	0.8232	82.32%
Androgen receptor binding	+	0.7987	79.87%
Thyroid receptor binding	-	0.5951	59.51%
Glucocorticoid receptor binding	+	0.6024	60.24%
Aromatase binding	+	0.7014	70.14%
PPAR gamma	+	0.5252	52.52%
Honey bee toxicity	-	0.7236	72.36%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9023	90.23%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.18%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.70%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.31%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.72%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.49%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.33%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.83%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.71%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.26%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.26%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.64%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.29%	97.36%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.37%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.54%	94.45%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.44%	92.32%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.65%	91.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.39%	92.94%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.32%	98.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.10%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.97%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.76%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.54%	92.62%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.13%	98.46%
CHEMBL226	P30542	Adenosine A1 receptor	80.41%	95.93%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 10099125
• NPASS: NPC197872
• LOTUS: LTS0007944
• wikiData: Q105329683