Asclepin

Details

• Internal ID: 9c0659e6-6e0d-42c0-b575-39c98a55207c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-14-formyl-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-9-yl] acetate
• SMILES (Canonical): CC1CC(C2(C(O1)OC3CC4CCC5C(C4(CC3O2)C=O)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@]2([C@@H](O1)O[C@@H]3C[C@@H]4CC[C@@H]5[C@@H]([C@]4(C[C@H]3O2)C=O)CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O)OC(=O)C
• InChI: InChI=1S/C31H42O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,15-16,19-25,27,35-36H,4-10,12-14H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1
• InChI Key: OXKMZIABKYHLAR-SVDYBJNLSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₂O₁₀
• Molecular Weight: 574.70 g/mol
• Exact Mass: 574.27779753 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Asclepiadin
• CHEBI:2867
• 36573-63-4
• 3'-O-Acetylcalotropin
• EINECS 253-110-8
• BRN 4897521
• Calotropin, 3'-O-acetyl-
• (2alpha(2S,3S,4S,6R),3beta,5alpha)-2,3-((4-Acetoxytetrahydro-3-hydroxy-6-methyl-2H-pyran-3,2-diyl)bis(oxy))-14-hydroxy-19-oxocard-20(22)-enolide
• [2alpha(2S,3S,4S,6R),3beta,5alpha]-2,3-[[4-acetoxytetrahydro-3-hydroxy-6-methyl-2H-pyran-3,2-diyl]bis(oxy)]-14-hydroxy-19-oxocard-20(22)-enolide
• Asclepin (Asclepiadin)
• CHEMBL445086
• DTXSID50957853
• (2alpha,3beta,5alpha)-3-((3-O-Acetyl-4,6-dideoxy-D-erythro-hexopyranos-2-ulos-1-yl)oxy) card-20(22)-enolide
• BDBM50277171
• C31H42O10
• C08849
• Q27105852
• 13a-formyl-3a,11a-dihydroxy-9,15a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)icosahydro-1h,7ah-cyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxin-11-yl acetate
• Card-20(22)-enolide, 3-[(3-O-acetyl-4,6-dideoxy-D-erythro-hexopyranos-2-ulos-1-yl)oxy]-2,14-dihydroxy-19-oxo-, (2.alpha.,3.beta.,5.alpha.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	-	0.8115	81.15%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8739	87.39%
OATP2B1 inhibitior	-	0.7145	71.45%
OATP1B1 inhibitior	+	0.8662	86.62%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.8883	88.83%
P-glycoprotein inhibitior	+	0.7126	71.26%
P-glycoprotein substrate	+	0.7267	72.67%
CYP3A4 substrate	+	0.7290	72.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9018	90.18%
CYP3A4 inhibition	-	0.8311	83.11%
CYP2C9 inhibition	-	0.9065	90.65%
CYP2C19 inhibition	-	0.9516	95.16%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.9105	91.05%
CYP2C8 inhibition	+	0.6005	60.05%
CYP inhibitory promiscuity	-	0.9302	93.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4706	47.06%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9349	93.49%
Skin irritation	+	0.5726	57.26%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3996	39.96%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.9196	91.96%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5567	55.67%
Acute Oral Toxicity (c)	I	0.9011	90.11%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.8108	81.08%
Thyroid receptor binding	-	0.5560	55.60%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.6990	69.90%
PPAR gamma	+	0.5453	54.53%
Honey bee toxicity	-	0.6611	66.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9839	98.39%

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	98.43%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.91%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.98%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.02%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.75%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.06%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.32%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.74%	82.69%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.88%	81.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	90.53%	93.04%
CHEMBL4208	P20618	Proteasome component C5	88.97%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.74%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.67%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.59%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.26%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.18%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.41%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.84%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.06%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.95%	91.19%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.76%	94.42%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.50%	92.86%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.46%	93.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.67%	90.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.46%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.31%	97.25%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Asclepias vestita
• Gomphocarpus fruticosus subsp. fruticosus
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 441844
• NPASS: NPC91
• ChEMBL: CHEMBL445086
• LOTUS: LTS0032666
• wikiData: Q27105852