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epsilon-Amanitin

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 2aca0a52-4133-46c7-86f2-fd6464748b41
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides > Amatoxins
IUPAC Name 2-[34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetic acid
SMILES (Canonical) CCC(C)C1C(=O)NCC(=O)NC2CS(=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)O)O)C(C)C(C)O)C5=C(N3)C=C(C=C5)O
SMILES (Isomeric) CCC(C)C1C(=O)NCC(=O)NC2CS(=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)O)O)C(C)C(C)O)C5=C(N3)C=C(C=C5)O
InChI InChI=1S/C39H53N9O14S/c1-5-16(2)31-36(59)41-12-28(52)42-26-15-63(62)38-22(21-7-6-19(50)8-23(21)45-38)10-24(33(56)40-13-29(53)46-31)43-37(60)32(17(3)18(4)49)47-35(58)27-9-20(51)14-48(27)39(61)25(11-30(54)55)44-34(26)57/h6-8,16-18,20,24-27,31-32,45,49-51H,5,9-15H2,1-4H3,(H,40,56)(H,41,59)(H,42,52)(H,43,60)(H,44,57)(H,46,53)(H,47,58)(H,54,55)
InChI Key OFILNAORONITPV-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C39H53N9O14S
Molecular Weight 904.00 g/mol
Exact Mass 903.34326857 g/mol
Topological Polar Surface Area (TPSA) 374.00 Ų
XlogP -2.70
Atomic LogP (AlogP) -4.29
H-Bond Acceptor 13
H-Bond Donor 12
Rotatable Bonds 6

Synonyms

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21705-02-2
2-[34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetic acid
DTXSID201028142
alpha-Amanitin, 1-L-aspartic acid-3-((S)-4-hydroxy-L-isoleucine)-
alpha-Amanitin, 1-L-aspartic acid-3-(4-hydroxy-L-isoleucine)-, (S)-
AKOS040757381
9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8,9)(1,5,8,11,14)thiatetraazacyclooctadecino(18,17-b)indole-6-acetic acid, 1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-2,14-dihydroxy-21-(2-hydroxy-1-methylpropyl)-5,8,20,23,24,27,30,33-octaoxo-, 11-oxide
Cyclo(L-alpha-aspartyl-4-hydroxy-L-prolyl-(S)-4-hydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl), cyclic (4-8)-sulfide, (R)-8-oxide

2D Structure

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2D Structure of epsilon-Amanitin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8167 81.67%
Caco-2 - 0.8711 87.11%
Blood Brain Barrier - 0.8250 82.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Lysosomes 0.4326 43.26%
OATP2B1 inhibitior - 0.5912 59.12%
OATP1B1 inhibitior + 0.7838 78.38%
OATP1B3 inhibitior + 0.9330 93.30%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9129 91.29%
P-glycoprotein inhibitior + 0.7353 73.53%
P-glycoprotein substrate + 0.8777 87.77%
CYP3A4 substrate + 0.7125 71.25%
CYP2C9 substrate - 0.8035 80.35%
CYP2D6 substrate - 0.8484 84.84%
CYP3A4 inhibition - 0.7854 78.54%
CYP2C9 inhibition - 0.7157 71.57%
CYP2C19 inhibition - 0.7074 70.74%
CYP2D6 inhibition - 0.8647 86.47%
CYP1A2 inhibition - 0.7103 71.03%
CYP2C8 inhibition + 0.7836 78.36%
CYP inhibitory promiscuity - 0.7557 75.57%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.5700 57.00%
Carcinogenicity (trinary) Non-required 0.6039 60.39%
Eye corrosion - 0.9824 98.24%
Eye irritation - 0.9078 90.78%
Skin irritation - 0.7633 76.33%
Skin corrosion - 0.9196 91.96%
Ames mutagenesis - 0.7054 70.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4366 43.66%
Micronuclear + 0.8700 87.00%
Hepatotoxicity - 0.6447 64.47%
skin sensitisation - 0.8410 84.10%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.8009 80.09%
Acute Oral Toxicity (c) III 0.5420 54.20%
Estrogen receptor binding + 0.8136 81.36%
Androgen receptor binding + 0.7440 74.40%
Thyroid receptor binding + 0.5797 57.97%
Glucocorticoid receptor binding + 0.5581 55.81%
Aromatase binding + 0.5966 59.66%
PPAR gamma + 0.7550 75.50%
Honey bee toxicity - 0.7111 71.11%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9595 95.95%

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 99.79% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.37% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 99.03% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.29% 91.11%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 95.00% 91.71%
CHEMBL255 P29275 Adenosine A2b receptor 92.92% 98.59%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.59% 89.00%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 92.11% 82.38%
CHEMBL5103 Q969S8 Histone deacetylase 10 91.92% 90.08%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.86% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.60% 97.09%
CHEMBL2535 P11166 Glucose transporter 90.58% 98.75%
CHEMBL1902 P62942 FK506-binding protein 1A 89.86% 97.05%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.14% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.87% 85.14%
CHEMBL1781 P11387 DNA topoisomerase I 88.61% 97.00%
CHEMBL226 P30542 Adenosine A1 receptor 87.79% 95.93%
CHEMBL206 P03372 Estrogen receptor alpha 86.91% 97.64%
CHEMBL217 P14416 Dopamine D2 receptor 86.32% 95.62%
CHEMBL4071 P08311 Cathepsin G 86.20% 94.64%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 86.10% 90.71%
CHEMBL2443 P49862 Kallikrein 7 85.72% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.54% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.46% 93.56%
CHEMBL213 P08588 Beta-1 adrenergic receptor 84.76% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.72% 95.89%
CHEMBL3310 Q96DB2 Histone deacetylase 11 84.44% 88.56%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 84.10% 96.90%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.05% 89.62%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 84.02% 93.40%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 83.98% 94.62%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.63% 93.00%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 83.37% 95.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.32% 86.33%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 83.05% 90.93%
CHEMBL1907 P15144 Aminopeptidase N 82.69% 93.31%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.50% 97.14%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.76% 94.08%
CHEMBL256 P0DMS8 Adenosine A3 receptor 80.52% 95.93%
CHEMBL1907594 P30926 Neuronal acetylcholine receptor; alpha3/beta4 80.15% 97.23%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.00% 95.89%

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.
Acanthochlamys bracteata

Cross-Links

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PubChem 30508
LOTUS LTS0126611
wikiData Q2760181