20,26-Dihydroxyecdysone

Details

• Internal ID: b1918b5b-56a4-45ae-953d-2f1a7aa76f37
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)O
• 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@](C)([C@@H](CCC(C)(CO)O)O)O)O
• InChI: InChI=1S/C27H44O8/c1-23(33,14-28)8-7-22(32)26(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-24(17,2)15(16)5-9-25(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22+,23?,24+,25+,26+,27+/m0/s1
• InChI Key: RRCGNPRHZQPOOT-FFBSXHGNSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₈
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.30361836 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 8
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• Podecdysone C
• 19458-46-9
• ergosta-5,24(28)-diene-3beta,20,26-triol
• 26-Hydroxy-beta-ecdysone
• SCHEMBL3412970
• CHEBI:19793
• HY-N10382
• LMST01010184
• CS-0498873
• E89033
• Q27109250
• (2beta,3beta,5beta,22R)-2,3,14,20,22,25,26-Heptahydroxycholest-7-en-6-one
• (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.6557	65.57%
Blood Brain Barrier	+	0.6135	61.35%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8335	83.35%
OATP2B1 inhibitior	-	0.5724	57.24%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9522	95.22%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5202	52.02%
BSEP inhibitior	+	0.7008	70.08%
P-glycoprotein inhibitior	-	0.6327	63.27%
P-glycoprotein substrate	+	0.5582	55.82%
CYP3A4 substrate	+	0.6942	69.42%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.8127	81.27%
CYP2C9 inhibition	-	0.8957	89.57%
CYP2C19 inhibition	-	0.9138	91.38%
CYP2D6 inhibition	-	0.9405	94.05%
CYP1A2 inhibition	-	0.9271	92.71%
CYP2C8 inhibition	-	0.6278	62.78%
CYP inhibitory promiscuity	-	0.9254	92.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7064	70.64%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9507	95.07%
Skin irritation	+	0.6209	62.09%
Skin corrosion	-	0.9599	95.99%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6708	67.08%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6110	61.10%
skin sensitisation	-	0.8944	89.44%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8768	87.68%
Acute Oral Toxicity (c)	III	0.6520	65.20%
Estrogen receptor binding	+	0.8012	80.12%
Androgen receptor binding	+	0.7365	73.65%
Thyroid receptor binding	+	0.5841	58.41%
Glucocorticoid receptor binding	+	0.7867	78.67%
Aromatase binding	+	0.6866	68.66%
PPAR gamma	-	0.5514	55.14%
Honey bee toxicity	-	0.8257	82.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9793	97.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.84%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.53%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.27%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.14%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.98%	97.09%
CHEMBL2581	P07339	Cathepsin D	95.49%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.22%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.23%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.37%	100.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	90.22%	94.78%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.39%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.00%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.31%	93.99%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.00%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.31%	97.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.82%	96.90%
CHEMBL2094135	Q96BI3	Gamma-secretase	84.05%	98.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.83%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.38%	86.33%
CHEMBL1871	P10275	Androgen Receptor	81.16%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.88%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.79%	89.00%
CHEMBL4805	Q99572	P2X purinoceptor 7	80.00%	97.50%

Plants that contains it

• Cyanotis arachnoidea

Cross-Links

• PubChem: 21123946
• LOTUS: LTS0058455
• wikiData: Q27109250