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Beauvericin
- Family: Fungi - Nectriaceae
- Kingdom: Fungi
-
Class: Peptide
- Subclass: Depsipeptide
| Canonical Smiles | CC([C@H]1OC(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](OC(=O)[C@@H](N(C(=O)[C@H](OC(=O)[C@@H](N(C1=O)C)Cc1ccccc1)C(C)C)C)Cc1ccccc1)C(C)C)C |
|---|---|
| InChI | InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1 |
| InChIKey | GYSCAQFHASJXRS-FFCOJMSVSA-N |
| Formula | C45H57N3O9 |
| HBA | 9 |
| HBD | 0 |
| MW | 783.96 |
| Rotatable Bonds | 9 |
| TPSA | 139.83 |
| LogP | 4.91 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 57 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.47 |
| Exact Mass | 783.41 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Fusarium sp. | Nectriaceae | Fungi | 29916 |
Showing of synonyms
Beauvericin
26048-05-5
UNII-26S048LS2R
CHEBI:3000
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
26S048LS2R
DTXSID00891834
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
DTXCID901031255
Cyclo(D-alpha-Hydroxyisovaleryl-L-N-methyl-Phe)3
1,7,13-Trioxa-4,10,16-triazacyclooctadecane, cyclic peptide deriv.
(3R,6S,9R,12S,15R,18S)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Cyclo(D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl)
Cyclo(D-alpha-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-alpha-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-alpha-hydroxyisovaleryl-N-methyl-L-phenylalanyl)
Cyclo((2r)-2-hydroxy-3-methylbutanoyl-n-methyl-l-phenylalanyl-(2r)-2-hydroxy-3-methylbutanoyl-n-methyl-l-phenylalanyl-(2r)-2-hydroxy-3-methylbutanoyl-n-methyl-l-phenylalanyl)
(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexaone
SCHEMBL29355
CHEMBL249052
MSK7258
GYSCAQFHASJXRS-FFCOJMSVSA-N
HY-N6739
MSK7258-100A
AKOS030622850
CS-W020817
FB18149
NCGC00380798-01
NS00018333
A12357
Beauvericin Solution in Acetonitrile, 100ug/mL
Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy -3-methylbutanoyl-N-methyl-L-phenylalanyl]
- Kongue Tatong M, Talontsi F, et al. (2014). Banchromene and other secondary metabolites from the endophytic fungus Fusarium sp. obtained from Piper guineense inhibit the motility of phytopathogenic Plasmopara viticola zoospores. Tetrahedron Letters, 2014, 55(30), 4057-4061. [View]
Pubchem:
3007984
Cas:
26048-05-5
Gnps:
CCMSLIB00005727241
Zinc:
ZINC000087496145
Chebi:
3000
Nmrshiftdb2:
80005001
Metabolights:
MTBLC3000
Chembl:
CHEMBL249052
Comptox:
DTXSID00891834
CPRiL:
39131
SMILES: c1ccccc1CC(C(=O)OCC2=O)NC(=O)COC(=O)C(Cc3ccccc3)NC(=O)COC(=O)C(N2)Cc4ccccc4
Level: 3
Mol. Weight: 783.96 g/mol
SMILES: c1ccccc1CC(C(=O)OCC2=O)NC(=O)COC(=O)CNC(=O)COC(=O)C(N2)Cc3ccccc3
Level: 2
Mol. Weight: 783.96 g/mol
SMILES: c1ccccc1CC(N2)C(=O)OCC(=O)NCC(=O)OCC(=O)NCC(=O)OCC2=O
Level: 1
Mol. Weight: 783.96 g/mol
SMILES: O=C1COC(=O)CNC(=O)COC(=O)CNC(=O)COC(=O)CN1
Level: 0
Mol. Weight: 783.96 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 783.96 g/mol
Cytotoxic
Motility-impairing
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 28.45
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 4395.23
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.96
- Plasma Protein Binding
- 76.36
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 6.73
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -107.06
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.8
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.92
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -7980481.94
- Rat (Acute)
- 3.65
- Rat (Chronic Oral)
- 1.4
- Fathead Minnow
- 10080.62
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 892987.87
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.69
- Log(P)
- 4.28
- Log S
- -5.03
- Log(Vapor Pressure)
- -29348.02
- Melting Point
- 268.83
- pKa Acid
- -175.37
- pKa Basic
- 5.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9607 |
| Carnitine O-palmitoyltransferase 2, mitochondrial | P18886 | CPT2_RAT | Rattus norvegicus | 3 | 0.9501 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.9354 |
| Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 3 | 0.8303 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8001 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7876 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7835 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 2 | 0.7725 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7700 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7643 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7610 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7608 |
| Nociceptin receptor | P41146 | OPRX_HUMAN | Homo sapiens | 3 | 0.7606 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7587 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7583 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7573 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7571 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7546 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7537 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7522 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7517 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7505 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7489 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7456 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7415 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7409 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7403 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7359 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7352 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7345 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7321 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7293 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7231 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7218 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7158 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7105 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7047 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7038 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7033 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7015 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7010 |