3-Epiecdysone

Details

• Internal ID: f599c8a5-948c-461f-a142-d00c2327b25c
• 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: (2S,3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
• SMILES (Isomeric): C[C@@H]([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)[C@@H](CCC(C)(C)O)O
• InChI: InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22-,23-,25+,26+,27+/m0/s1
• InChI Key: UPEZCKBFRMILAV-LVRQXCCVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₆
• Molecular Weight: 464.60 g/mol
• Exact Mass: 464.31378912 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.74
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• CHEBI:80531
• Q27149575
• (2S,3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-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	+	0.9938	99.38%
Caco-2	-	0.5171	51.71%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8310	83.10%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8038	80.38%
P-glycoprotein inhibitior	-	0.6317	63.17%
P-glycoprotein substrate	+	0.5965	59.65%
CYP3A4 substrate	+	0.6635	66.35%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	-	0.7154	71.54%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9557	95.57%
Skin irritation	+	0.6543	65.43%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4532	45.32%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5311	53.11%
skin sensitisation	-	0.7034	70.34%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8622	86.22%
Acute Oral Toxicity (c)	III	0.5365	53.65%
Estrogen receptor binding	+	0.7713	77.13%
Androgen receptor binding	+	0.7905	79.05%
Thyroid receptor binding	+	0.6047	60.47%
Glucocorticoid receptor binding	+	0.7799	77.99%
Aromatase binding	+	0.6475	64.75%
PPAR gamma	-	0.5861	58.61%
Honey bee toxicity	-	0.8475	84.75%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9934	99.34%

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	99.84%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.72%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.04%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.21%	82.69%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	92.89%	94.78%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.53%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.13%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.66%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.42%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.78%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	86.60%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	85.73%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.34%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.30%	97.14%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.11%	98.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.80%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.37%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.61%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.26%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.92%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	81.32%	97.05%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.83%	85.31%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.58%	91.07%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Ophryosporus floribundus
• Payena lucida
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Pteridium aquilinum
• Quassia indica
• Rivina humilis

Cross-Links

• PubChem: 23724769
• NPASS: NPC45188
• LOTUS: LTS0241762
• wikiData: Q27149575