16alpha-Acetoxyasclepin

Details

• Internal ID: 58723be8-d30e-425b-b897-1c298994d344
• 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,20R,22S,23R)-20-acetyloxy-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(CC(C6C7=CC(=O)OC7)OC(=O)C)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(C[C@H]([C@@H]6C7=CC(=O)OC7)OC(=O)C)O)C)O)OC(=O)C
• InChI: InChI=1S/C33H44O12/c1-16-9-26(43-18(3)36)33(39)29(41-16)44-23-11-20-5-6-22-21(31(20,15-34)12-24(23)45-33)7-8-30(4)28(19-10-27(37)40-14-19)25(42-17(2)35)13-32(22,30)38/h10,15-16,20-26,28-29,38-39H,5-9,11-14H2,1-4H3/t16-,20+,21+,22-,23-,24-,25-,26+,28+,29+,30-,31-,32+,33+/m1/s1
• InChI Key: WDMVIHZXOHPIHJ-MCQWJBQLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₂
• Molecular Weight: 632.70 g/mol
• Exact Mass: 632.28327683 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEMBL454779

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9774	97.74%
Caco-2	-	0.8432	84.32%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8739	87.39%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.7919	79.19%
P-glycoprotein inhibitior	+	0.7498	74.98%
P-glycoprotein substrate	+	0.7265	72.65%
CYP3A4 substrate	+	0.7361	73.61%
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	+	0.7031	70.31%
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	-	0.9282	92.82%
Skin irritation	+	0.5726	57.26%
Skin corrosion	-	0.9346	93.46%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4831	48.31%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5709	57.09%
skin sensitisation	-	0.9196	91.96%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6477	64.77%
Acute Oral Toxicity (c)	I	0.9011	90.11%
Estrogen receptor binding	+	0.7866	78.66%
Androgen receptor binding	+	0.7861	78.61%
Thyroid receptor binding	-	0.5610	56.10%
Glucocorticoid receptor binding	+	0.7215	72.15%
Aromatase binding	+	0.6782	67.82%
PPAR gamma	+	0.6460	64.60%
Honey bee toxicity	-	0.6377	63.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
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	98.51%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.26%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.47%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.30%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.06%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.59%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.90%	91.11%
CHEMBL4208	P20618	Proteasome component C5	90.17%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.01%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.76%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	88.26%	81.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.96%	93.04%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.59%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.53%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.62%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.43%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.07%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.82%	97.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.42%	97.36%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.83%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.69%	93.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.58%	94.42%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.57%	92.86%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.30%	97.09%
CHEMBL5028	O14672	ADAM10	81.81%	97.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.88%	90.24%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.84%	97.33%

Plants that contains it

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

Cross-Links

• PubChem: 10054800
• NPASS: NPC142756
• ChEMBL: CHEMBL454779
• LOTUS: LTS0262884
• wikiData: Q105302532