Ergoptin

Details

• Internal ID: fbb9ea95-3c39-42f2-91ef-61ab41c1975b
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7R)-4-ethyl-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-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)CC(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)CC(C)C)NC(=O)[C@H]4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C
• InChI: InChI=1S/C31H39N5O5/c1-5-30(29(39)36-24(12-17(2)3)28(38)35-11-7-10-25(35)31(36,40)41-30)33-27(37)19-13-21-20-8-6-9-22-26(20)18(15-32-22)14-23(21)34(4)16-19/h6,8-9,13,15,17,19,23-25,32,40H,5,7,10-12,14,16H2,1-4H3,(H,33,37)/t19-,23-,24-,25+,30-,31+/m1/s1
• InChI Key: JFRCRHHCXKEHBW-YKAZNSBZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₉N₅O₅
• Molecular Weight: 561.70 g/mol
• Exact Mass: 561.29511936 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 29475-05-6
• alpha-Ergoptine
• (6aR,9R)-N-[(1S,2S,4R,7R)-4-ethyl-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-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
• Ergotaman-3',6',18-trione, 2'-ethyl-12'-hydroxy-5'-(2-methylpropyl)-, (5'-alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	-	0.8153	81.53%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9714	97.14%
Subcellular localzation	Nucleus	0.3032	30.32%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.8590	85.90%
OATP1B3 inhibitior	+	0.9155	91.55%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9560	95.60%
P-glycoprotein inhibitior	+	0.9249	92.49%
P-glycoprotein substrate	+	0.7310	73.10%
CYP3A4 substrate	+	0.7849	78.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.7879	78.79%
CYP2C9 inhibition	-	0.9095	90.95%
CYP2C19 inhibition	-	0.7939	79.39%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	+	0.7178	71.78%
CYP2C8 inhibition	+	0.5559	55.59%
CYP inhibitory promiscuity	-	0.7894	78.94%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4668	46.68%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9616	96.16%
Skin irritation	-	0.7529	75.29%
Skin corrosion	-	0.9222	92.22%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7011	70.11%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.8009	80.09%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8135	81.35%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.8583	85.83%
Androgen receptor binding	+	0.8228	82.28%
Thyroid receptor binding	+	0.5254	52.54%
Glucocorticoid receptor binding	+	0.7486	74.86%
Aromatase binding	+	0.7895	78.95%
PPAR gamma	+	0.8121	81.21%
Honey bee toxicity	-	0.7830	78.30%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5641	56.41%
Fish aquatic toxicity	+	0.9792	97.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.18%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.86%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.69%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.73%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	92.15%	95.62%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.11%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.99%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.74%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.56%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.59%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.48%	91.11%
CHEMBL2094135	Q96BI3	Gamma-secretase	90.26%	98.05%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.00%	96.47%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	89.18%	97.64%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	89.03%	83.10%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	88.92%	95.00%
CHEMBL4073	P09237	Matrix metalloproteinase 7	88.68%	97.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.14%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.83%	90.08%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.79%	97.50%
CHEMBL3524	P56524	Histone deacetylase 4	87.45%	92.97%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.02%	99.23%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.80%	85.11%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.63%	98.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.37%	94.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.20%	99.18%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.55%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.99%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.95%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.30%	95.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.53%	88.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.04%	96.77%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.74%	89.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.67%	96.21%

Plants that contains it

• Festuca rubra

Cross-Links

• PubChem: 161635
• LOTUS: LTS0227422
• wikiData: Q105126853