Ergotinine

Details

• Internal ID: e56333a2-0d6e-4f07-bd1a-55e39a6e0c2f
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines > Ergotamines, dihydroergotamines, and derivatives
• IUPAC Name: (6aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-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;(6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(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;(6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-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): CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O.CC(C)C1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=CNC7=CC=CC(=C67)C5=C4)C)O.CC(C)C1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C
• SMILES (Isomeric): CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)C4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O.CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)C4CN([C@@H]5CC6=CNC7=CC=CC(=C67)C5=C4)C)O.CC(C)[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C
• InChI: InChI=1S/C35H39N5O5.C32H41N5O5.C31H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34;1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20;1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41);6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38);6,8-9,12,14,16-17,19,23-24,26,32,40H,7,10-11,13,15H2,1-5H3,(H,33,37)/t23?,27-,28+,29+,34-,35+;20?,24-,25+,26+,31-,32+;19?,23-,24+,26+,30-,31+/m111/s1
• InChI Key: QOTUIZVGUVLMNQ-GJLSPIEVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉₈H₁₁₉N₁₅O₁₅
• Molecular Weight: 1747.10 g/mol
• Exact Mass: 1746.90436298 g/mol
• Topological Polar Surface Area (TPSA): 355.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 7.10
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 14

Synonyms

• Ergotoxinine
• UNII-J6AIY5049X
• J6AIY5049X
• 8006-08-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9574	95.74%
Caco-2	-	0.8513	85.13%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Nucleus	0.3901	39.01%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8377	83.77%
OATP1B3 inhibitior	+	0.9074	90.74%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9846	98.46%
P-glycoprotein inhibitior	+	0.7884	78.84%
P-glycoprotein substrate	+	0.7168	71.68%
CYP3A4 substrate	+	0.7906	79.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.8487	84.87%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.7688	76.88%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7371	73.71%
CYP inhibitory promiscuity	-	0.6627	66.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.7424	74.24%
Skin corrosion	-	0.9235	92.35%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7678	76.78%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.8153	81.53%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8663	86.63%
Acute Oral Toxicity (c)	III	0.6051	60.51%
Estrogen receptor binding	+	0.8050	80.50%
Androgen receptor binding	+	0.7779	77.79%
Thyroid receptor binding	+	0.6823	68.23%
Glucocorticoid receptor binding	+	0.7396	73.96%
Aromatase binding	+	0.6451	64.51%
PPAR gamma	+	0.8153	81.53%
Honey bee toxicity	-	0.7144	71.44%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.96%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.88%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.56%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.42%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.39%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.44%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	95.43%	93.03%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.38%	97.64%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.24%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.57%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.98%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.92%	94.45%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	89.70%	95.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.77%	96.47%
CHEMBL3524	P56524	Histone deacetylase 4	88.69%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.22%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.88%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.78%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.40%	97.09%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	87.40%	98.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.52%	85.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.47%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.66%	90.08%
CHEMBL217	P14416	Dopamine D2 receptor	84.49%	95.62%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.31%	83.10%
CHEMBL3837	P07711	Cathepsin L	83.29%	96.61%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.26%	97.50%
CHEMBL5747	Q92793	CREB-binding protein	83.22%	95.12%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.04%	92.67%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	82.04%	91.43%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.03%	89.67%
CHEMBL5203	P33316	dUTP pyrophosphatase	81.24%	99.18%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.98%	97.14%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.83%	96.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.38%	93.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.33%	96.67%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.26%	95.71%
CHEMBL4208	P20618	Proteasome component C5	80.18%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 131750167
• LOTUS: LTS0105583
• wikiData: Q104401805