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Ergotoxine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 35d2aa4b-95d0-4b0d-912c-efba0eb43424
Taxonomy Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines
IUPAC Name (6aR,9R)-N-[(1S,2S,4R)-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
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C28H33N5O5/c1-15(2)27(26(36)33-14-23(34)32-9-5-8-22(32)28(33,37)38-27)30-25(35)17-10-19-18-6-4-7-20-24(18)16(12-29-20)11-21(19)31(3)13-17/h4,6-7,10,12,15,17,21-22,29,37H,5,8-9,11,13-14H2,1-3H3,(H,30,35)/t17-,21-,22+,27-,28+/m1/s1
InChI Key XLMJRFCCCWFQRE-SJRQCXNHSA-N
Popularity 72 references in papers

Physical and Chemical Properties

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Molecular Formula C28H33N5O5
Molecular Weight 519.60 g/mol
Exact Mass 519.24816917 g/mol
Topological Polar Surface Area (TPSA) 118.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.02
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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ERGOTOXINE
Ergotoxin
8006-25-5
DTXSID90230056
2J09Y26C6I
(6aR,9R)-N-[(1S,2S,4R)-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,9R)-N-((1S,2S,4R)-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
RefChem:591077
DTXCID90152547
2'beta-Isopropylergopeptine
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Ergotoxine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9701 97.01%
Caco-2 - 0.8069 80.69%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Nucleus 0.3217 32.17%
OATP2B1 inhibitior - 0.7103 71.03%
OATP1B1 inhibitior + 0.8761 87.61%
OATP1B3 inhibitior + 0.9083 90.83%
MATE1 inhibitior + 0.9967 99.67%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9236 92.36%
P-glycoprotein inhibitior + 0.8052 80.52%
P-glycoprotein substrate + 0.7328 73.28%
CYP3A4 substrate + 0.7858 78.58%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7671 76.71%
CYP3A4 inhibition + 0.6243 62.43%
CYP2C9 inhibition - 0.9242 92.42%
CYP2C19 inhibition - 0.6597 65.97%
CYP2D6 inhibition - 0.9414 94.14%
CYP1A2 inhibition + 0.8375 83.75%
CYP2C8 inhibition + 0.5409 54.09%
CYP inhibitory promiscuity - 0.8490 84.90%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.4762 47.62%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9676 96.76%
Skin irritation - 0.7426 74.26%
Skin corrosion - 0.9247 92.47%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6831 68.31%
Micronuclear + 0.8600 86.00%
Hepatotoxicity - 0.6871 68.71%
skin sensitisation - 0.8657 86.57%
Respiratory toxicity + 0.9778 97.78%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 1.0000 100.00%
Nephrotoxicity - 0.5714 57.14%
Acute Oral Toxicity (c) III 0.5778 57.78%
Estrogen receptor binding + 0.7745 77.45%
Androgen receptor binding + 0.7836 78.36%
Thyroid receptor binding - 0.5415 54.15%
Glucocorticoid receptor binding + 0.7448 74.48%
Aromatase binding + 0.7398 73.98%
PPAR gamma + 0.7464 74.64%
Honey bee toxicity - 0.7773 77.73%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.5350 53.50%
Fish aquatic toxicity + 0.9794 97.94%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2581 P07339 Cathepsin D 99.76% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.02% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.39% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 96.30% 91.49%
CHEMBL5608 Q16288 NT-3 growth factor receptor 95.62% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.29% 91.11%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 94.62% 93.03%
CHEMBL217 P14416 Dopamine D2 receptor 93.48% 95.62%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.43% 85.14%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 93.13% 82.69%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.58% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.69% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.09% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.44% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.12% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.83% 94.45%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 88.41% 97.64%
CHEMBL1795139 Q8IU80 Transmembrane protease serine 6 86.72% 98.33%
CHEMBL3830 Q2M2I8 Adaptor-associated kinase 86.63% 83.10%
CHEMBL3310 Q96DB2 Histone deacetylase 11 84.96% 88.56%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 84.51% 83.00%
CHEMBL5203 P33316 dUTP pyrophosphatase 84.42% 99.18%
CHEMBL4208 P20618 Proteasome component C5 83.86% 90.00%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 83.73% 97.50%
CHEMBL5103 Q969S8 Histone deacetylase 10 83.57% 90.08%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.26% 93.04%
CHEMBL2535 P11166 Glucose transporter 82.84% 98.75%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.68% 93.56%
CHEMBL4073 P09237 Matrix metalloproteinase 7 82.61% 97.56%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 82.20% 96.47%
CHEMBL5747 Q92793 CREB-binding protein 81.74% 95.12%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 81.36% 85.11%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.33% 95.71%
CHEMBL213 P08588 Beta-1 adrenergic receptor 81.26% 95.56%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 80.73% 95.00%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 80.41% 92.67%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
There are no matching plants.

Cross-Links

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PubChem 3084035
LOTUS LTS0047152
wikiData Q27251515