Ergonine

Details

• Internal ID: 83466656-ae25-458d-9b3a-8960c56e6556
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7S)-4-ethyl-2-hydroxy-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• SMILES (Canonical): CCC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C
• SMILES (Isomeric): CC[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)C(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C
• InChI: InChI=1S/C30H37N5O5/c1-5-29(28(38)35-25(16(2)3)27(37)34-11-7-10-23(34)30(35,39)40-29)32-26(36)18-12-20-19-8-6-9-21-24(19)17(14-31-21)13-22(20)33(4)15-18/h6,8-9,12,14,16,18,22-23,25,31,39H,5,7,10-11,13,15H2,1-4H3,(H,32,36)/t18-,22-,23+,25+,29-,30+/m1/s1
• InChI Key: XWTYUTWHTOOWSS-LHBBTEICSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₇N₅O₅
• Molecular Weight: 547.60 g/mol
• Exact Mass: 547.27946930 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 29537-61-9
• Ergotaman-3',6',18-trione, 2'-ethyl-12'-hydroxy-5'-(1-methylethyl)-, (5'alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9731	97.31%
Caco-2	-	0.8263	82.63%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Nucleus	0.3232	32.32%
OATP2B1 inhibitior	-	0.5682	56.82%
OATP1B1 inhibitior	+	0.8529	85.29%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9550	95.50%
P-glycoprotein inhibitior	+	0.6783	67.83%
P-glycoprotein substrate	+	0.7642	76.42%
CYP3A4 substrate	+	0.7759	77.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.7778	77.78%
CYP2C9 inhibition	-	0.9132	91.32%
CYP2C19 inhibition	-	0.6983	69.83%
CYP2D6 inhibition	-	0.9207	92.07%
CYP1A2 inhibition	+	0.7325	73.25%
CYP2C8 inhibition	+	0.5376	53.76%
CYP inhibitory promiscuity	-	0.7785	77.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4752	47.52%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9633	96.33%
Skin irritation	-	0.7543	75.43%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8078	80.78%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.8224	82.24%
skin sensitisation	-	0.8632	86.32%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8884	88.84%
Acute Oral Toxicity (c)	III	0.5799	57.99%
Estrogen receptor binding	+	0.8409	84.09%
Androgen receptor binding	+	0.7256	72.56%
Thyroid receptor binding	+	0.5204	52.04%
Glucocorticoid receptor binding	+	0.7534	75.34%
Aromatase binding	+	0.8062	80.62%
PPAR gamma	+	0.8042	80.42%
Honey bee toxicity	-	0.7871	78.71%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9656	96.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.87%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.56%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.16%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.86%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.21%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.14%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	93.08%	95.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.67%	82.69%
CHEMBL1951	P21397	Monoamine oxidase A	91.48%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.46%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.62%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.25%	99.23%
CHEMBL4073	P09237	Matrix metalloproteinase 7	88.60%	97.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	88.58%	97.64%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	88.42%	83.10%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.09%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.03%	94.45%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.77%	97.50%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.60%	98.05%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.69%	96.47%
CHEMBL3524	P56524	Histone deacetylase 4	86.46%	92.97%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.37%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.82%	96.77%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.72%	90.08%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.28%	85.11%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.99%	88.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.47%	94.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	83.25%	98.33%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.06%	99.18%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	82.72%	95.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.92%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.08%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.71%	89.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.67%	91.24%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.50%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.27%	100.00%

Plants that contains it

• Festuca arundinacea
• Hippeastrum puniceum

Cross-Links

• PubChem: 13274438
• LOTUS: LTS0179747
• wikiData: Q75063012