Ecdysterone 20,22-monoacetonide

Details

• Internal ID: 36d5a064-4981-4b49-83c1-cfb5c555a520
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cholestane steroids > Cholesterols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)CCC(C)(C)O)C
• SMILES (Isomeric): C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@@]5([C@H](OC(O5)(C)C)CCC(C)(C)O)C)O
• InChI: InChI=1S/C30H48O7/c1-25(2,34)11-10-24-29(7,37-26(3,4)36-24)23-9-13-30(35)18-14-20(31)19-15-21(32)22(33)16-27(19,5)17(18)8-12-28(23,30)6/h14,17,19,21-24,32-35H,8-13,15-16H2,1-7H3/t17-,19-,21+,22-,23-,24+,27+,28+,29+,30+/m0/s1
• InChI Key: GXNNYSDWRVKVJY-VUYJMULXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₇
• Molecular Weight: 520.70 g/mol
• Exact Mass: 520.34000387 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 22798-96-5
• 20-Hydroxyecdysone 20,22-acetonide
• CHEMBL2087536
• DTXSID501346563
• (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• AKOS037623238
• FS-9622

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	-	0.5193	51.93%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8363	83.63%
OATP2B1 inhibitior	-	0.7180	71.80%
OATP1B1 inhibitior	+	0.8727	87.27%
OATP1B3 inhibitior	+	0.9027	90.27%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6712	67.12%
P-glycoprotein inhibitior	-	0.4716	47.16%
P-glycoprotein substrate	+	0.5112	51.12%
CYP3A4 substrate	+	0.6929	69.29%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8883	88.83%
CYP3A4 inhibition	-	0.6127	61.27%
CYP2C9 inhibition	-	0.8367	83.67%
CYP2C19 inhibition	-	0.8282	82.82%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.8942	89.42%
CYP2C8 inhibition	+	0.4628	46.28%
CYP inhibitory promiscuity	-	0.8604	86.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4437	44.37%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9309	93.09%
Skin irritation	+	0.5889	58.89%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.7324	73.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.3882	38.82%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6004	60.04%
skin sensitisation	-	0.8228	82.28%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8649	86.49%
Acute Oral Toxicity (c)	III	0.4361	43.61%
Estrogen receptor binding	+	0.7109	71.09%
Androgen receptor binding	+	0.7672	76.72%
Thyroid receptor binding	+	0.5799	57.99%
Glucocorticoid receptor binding	+	0.7975	79.75%
Aromatase binding	+	0.7558	75.58%
PPAR gamma	+	0.5406	54.06%
Honey bee toxicity	-	0.8034	80.34%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9939	99.39%

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	98.99%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.85%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.43%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.69%	96.61%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.22%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.84%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.30%	97.28%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.15%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.63%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.96%	82.69%
CHEMBL2581	P07339	Cathepsin D	88.87%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.78%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.45%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.94%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.85%	86.33%
CHEMBL1871	P10275	Androgen Receptor	81.75%	96.43%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.72%	91.07%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.67%	94.78%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	81.11%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.73%	96.77%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.54%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.44%	92.62%

Plants that contains it

• Klasea centauroides subsp. strangulata
• Rhaponticum carthamoides subsp. carthamoides
• Serratula coronata
• Serratula coronata subsp. coronata
• Sida spinosa
• Stachyurus himalaicus

Cross-Links

• PubChem: 11060391
• LOTUS: LTS0136116
• wikiData: Q105023223