20-Hydroxyecdysone 22-acetate

Details

• Internal ID: dc57ceae-b8d0-487f-911f-fbb6c5887271
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Pentahydroxy bile acids, alcohols and derivatives
• IUPAC Name: [(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC(CCC(C)(C)O)C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• SMILES (Isomeric): CC(=O)O[C@H](CCC(C)(C)O)[C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O
• InChI: InChI=1S/C29H46O8/c1-16(30)37-24(9-10-25(2,3)34)28(6,35)23-8-12-29(36)18-13-20(31)19-14-21(32)22(33)15-26(19,4)17(18)7-11-27(23,29)5/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1
• InChI Key: YAIZECBIJHIPCU-FORVDKSSSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₆O₈
• Molecular Weight: 522.70 g/mol
• Exact Mass: 522.31926842 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 22799-02-6
• [(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] acetate
• CHEMBL2087165
• DTXSID90575676
• J-014861
• (2beta,3beta,5beta,22R)-2,3,14,20,25-Pentahydroxy-6-oxocholest-7-en-22-yl acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	-	0.5739	57.39%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8869	88.69%
OATP2B1 inhibitior	-	0.5745	57.45%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	-	0.3276	32.76%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7532	75.32%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	-	0.4571	45.71%
P-glycoprotein substrate	+	0.6010	60.10%
CYP3A4 substrate	+	0.7156	71.56%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.9063	90.63%
CYP3A4 inhibition	-	0.7658	76.58%
CYP2C9 inhibition	-	0.8151	81.51%
CYP2C19 inhibition	-	0.8483	84.83%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.8927	89.27%
CYP2C8 inhibition	+	0.4875	48.75%
CYP inhibitory promiscuity	-	0.9088	90.88%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7145	71.45%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9403	94.03%
Skin irritation	+	0.6610	66.10%
Skin corrosion	-	0.9504	95.04%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7006	70.06%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5561	55.61%
skin sensitisation	-	0.7838	78.38%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6531	65.31%
Acute Oral Toxicity (c)	IV	0.4457	44.57%
Estrogen receptor binding	+	0.7685	76.85%
Androgen receptor binding	+	0.7321	73.21%
Thyroid receptor binding	+	0.5340	53.40%
Glucocorticoid receptor binding	+	0.7665	76.65%
Aromatase binding	+	0.7183	71.83%
PPAR gamma	+	0.5401	54.01%
Honey bee toxicity	-	0.7494	74.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.50%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.02%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	97.56%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.09%	97.09%
CHEMBL2581	P07339	Cathepsin D	95.02%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.23%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.84%	94.45%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	91.04%	94.78%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.73%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.04%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.79%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.43%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.07%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.80%	96.61%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.76%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.53%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.85%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.91%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.35%	95.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.70%	95.89%
CHEMBL4805	Q99572	P2X purinoceptor 7	81.42%	97.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.33%	85.31%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.39%	98.75%

Plants that contains it

• Ajuga reptans
• Digitalis purpurea
• Silene turkestanica

Cross-Links

• PubChem: 15607741
• LOTUS: LTS0197787
• wikiData: Q82465092