Echinulin

Details

• Internal ID: a7235e0f-f69e-496e-93dc-0b2d903b6a6f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: (3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
• SMILES (Canonical): CC1C(=O)NC(C(=O)N1)CC2=C(NC3=C(C=C(C=C23)CC=C(C)C)CC=C(C)C)C(C)(C)C=C
• SMILES (Isomeric): C[C@H]1C(=O)N[C@H](C(=O)N1)CC2=C(NC3=C(C=C(C=C23)CC=C(C)C)CC=C(C)C)C(C)(C)C=C
• InChI: InChI=1S/C29H39N3O2/c1-9-29(7,8)26-23(16-24-28(34)30-19(6)27(33)31-24)22-15-20(12-10-17(2)3)14-21(25(22)32-26)13-11-18(4)5/h9-11,14-15,19,24,32H,1,12-13,16H2,2-8H3,(H,30,34)(H,31,33)/t19-,24-/m0/s1
• InChI Key: DIKMWTRJIZQJMY-CYFREDJKSA-N
• Popularity: 88 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₉N₃O₂
• Molecular Weight: 461.60 g/mol
• Exact Mass: 461.30422750 g/mol
• Topological Polar Surface Area (TPSA): 74.00 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• Echinuline
• 1859-87-6
• UNII-3DP19VPN8U
• 3DP19VPN8U
• CHEMBL251450
• (3S,6S)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]piperazine-2,5-dione
• 2,5-Piperazinedione, 3-((2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl)methyl)-6-methyl-, (3S,6S)-
• (3s,6s)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-5,7-bis(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}piperazine-2,5-dione
• C29H39N3O2
• 2,5-Piperazinedione, 3-[[2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-, (3S,6S)-
• ECHINULINE [MI]
• CHEBI:68193
• BAA85987
• HY-N3796
• BDBM50223401
• AKOS030213189
• NCGC00386111-01
• CS-0024238
• Q27257084
• (3S,6S)-3-[[2-(1,1-dimethyl-2-propen-1-yl)-5,7-bis(3-methyl-2-buten-1-yl)-1H-indol-3-yl]methyl]-6-methyl-2,5-piperazinedione
• (3S,6S)-3-[[2-(1,1-dimethylallyl)-5,7-bis(3-methylbut-2-enyl)-1H-indol-3-yl]methyl]-6-methyl-piperazine-2,5-dione
• 2,5-Piperazinedione, 3-[[2-(1,1-dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl]methyl]-6-methyl-, (3S-cis)-
• 3-((2-(1,1-Dimethyl-2-propenyl)-5,7-bis(3-methyl-2-butenyl)-1H-indol-3-yl)methyl)-6-methyl-2,5-piperazinedione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	-	0.7566	75.66%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5487	54.87%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8451	84.51%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7399	73.99%
BSEP inhibitior	+	0.9841	98.41%
P-glycoprotein inhibitior	+	0.8095	80.95%
P-glycoprotein substrate	+	0.6080	60.80%
CYP3A4 substrate	+	0.6232	62.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8311	83.11%
CYP3A4 inhibition	-	0.5084	50.84%
CYP2C9 inhibition	+	0.5327	53.27%
CYP2C19 inhibition	+	0.5613	56.13%
CYP2D6 inhibition	-	0.7768	77.68%
CYP1A2 inhibition	-	0.6106	61.06%
CYP2C8 inhibition	-	0.5681	56.81%
CYP inhibitory promiscuity	+	0.8383	83.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5925	59.25%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9725	97.25%
Skin irritation	-	0.7786	77.86%
Skin corrosion	-	0.9234	92.34%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8059	80.59%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8257	82.57%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8289	82.89%
Acute Oral Toxicity (c)	III	0.4897	48.97%
Estrogen receptor binding	+	0.6951	69.51%
Androgen receptor binding	+	0.5891	58.91%
Thyroid receptor binding	+	0.7096	70.96%
Glucocorticoid receptor binding	+	0.6473	64.73%
Aromatase binding	+	0.6113	61.13%
PPAR gamma	+	0.8219	82.19%
Honey bee toxicity	-	0.8214	82.14%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.29%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.59%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.93%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.14%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.33%	89.34%
CHEMBL4040	P28482	MAP kinase ERK2	92.56%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	92.45%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	90.91%	94.75%
CHEMBL255	P29275	Adenosine A2b receptor	89.68%	98.59%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.85%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	88.15%	97.05%
CHEMBL1951	P21397	Monoamine oxidase A	88.13%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.24%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.13%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.08%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.86%	93.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.62%	90.08%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.06%	96.90%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.69%	93.03%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.52%	92.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.82%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.35%	95.56%

Plants that contains it

• Cymbidium aloifolium
• Dendrobium fimbriatum
• Erythrophleum fordii
• Oroxylum indicum

Cross-Links

• PubChem: 115252
• NPASS: NPC67056
• LOTUS: LTS0256362
• wikiData: Q27257084