NP-MRD: Showing NP-Card for (3r,6s,9r,12s,15r,18s)-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 (NP0199700)

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Record Information

Version

2.0

Created at

2022-09-04 18:23:18 UTC

Updated at

2022-09-04 18:23:18 UTC

NP-MRD ID

NP0199700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6s,9r,12s,15r,18s)-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

Description

Beauvericin belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. (3r,6s,9r,12s,15r,18s)-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 is found in Cordyceps polyarthra, Cordyceps tenuipes, Fusarium incarnatum and Fusarium subglutinans. (3r,6s,9r,12s,15r,18s)-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 was first documented in 2022 (PMID: 36006229). Based on a literature review a small amount of articles have been published on Beauvericin (PMID: 36009000) (PMID: 36016515) (PMID: 35887419) (PMID: 35878215).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220232D          

 57 60  0  0  1  0            999 V2000
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 39 43  1  0  0  0  0
 43 44  1  0  0  0  0
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 44 46  1  0  0  0  0
 46 47  1  6  0  0  0
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 48 53  1  0  0  0  0
 46 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
  4 56  1  0  0  0  0
 56 57  2  0  0  0  0
M  END

     RDKit          3D

114117  0  0  0  0  0  0  0  0999 V2000
   -3.6989   -0.0551    2.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255   -0.7774    1.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8399    1.5819   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460    1.8569   -1.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105    2.8167    0.4056 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3084    3.3689    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6357    3.7030   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    2.7747   -1.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189    3.0904   -3.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    4.3555   -3.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784    5.2794   -2.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703    4.9559   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4861    2.6934    1.7720 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009    3.1124    2.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    2.2403    2.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    1.3459    3.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1091    2.6826    1.7893 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4318    4.0676    2.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0978    4.0314    3.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186    4.2962    2.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4468    0.4641    0.7232 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4187    1.1952    1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666   -0.7722    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -1.4372    1.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4450   -2.5455    1.9648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044   -2.2344    3.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907   -3.6520    1.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668   -1.6173   -0.1859 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707   -1.6498   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674   -0.6262   -1.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569   -2.7389   -1.5748 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6394   -3.9259   -0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -4.9059   -1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5957   -0.3551    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8057   -2.2543    2.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4525    1.7529   -1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9712    2.3501   -3.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873    4.6202   -4.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    6.2655   -3.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9196    5.7522   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    2.5078    3.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165    2.9277    2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9245    4.8739    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1950    5.3377    2.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176    3.6368    2.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2701    4.1791    1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3201   -0.4508   -3.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3088   -1.7941   -3.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4268   -1.4169   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4665    0.3598   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5111    1.7185   -0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6231    2.2093    1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0199700

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C1=O)C(C)C)C(C)C

> <INCHI_IDENTIFIER>
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+/m1/s1

> <INCHI_KEY>
GYSCAQFHASJXRS-WXWJZEDASA-N

> <FORMULA>
C45H57N3O9

> <MOLECULAR_WEIGHT>
783.963

> <EXACT_MASS>
783.409480427

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
84.41674370070734

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6S,9R,12S,15R,18S)-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

> <JCHEM_LOGP>
7.270860792

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.27886167110309

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.801215828238643

> <JCHEM_PKA_STRONGEST_BASIC>
-5.974714378619089

> <JCHEM_POLAR_SURFACE_AREA>
139.83

> <JCHEM_REFRACTIVITY>
213.46890000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S,9R,12S,15R,18S)-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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -5.335   6.160   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001  16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -8.002  10.780   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.336  13.090   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -12.003  11.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -13.337  10.780   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -12.003  13.090   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -10.669   9.240   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -13.337   9.240   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -16.004   6.160   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -17.338   6.930   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -17.338   8.470   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -16.004   9.240   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -14.670   8.470   0.000  0.00  0.00           C+0
HETATM   54  N   UNK     0     -10.669   6.160   0.000  0.00  0.00           N+0
HETATM   55  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0     -12.003   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   56                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    8   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   27   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   39   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   48                                                       
CONECT   54   46   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    4   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₅₇N₃O₉

Average Mass

783.9630 Da

Monoisotopic Mass

783.40948 Da

IUPAC Name

(3R,6S,9R,12S,15R,18S)-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

Traditional Name

(3R,6S,9R,12S,15R,18S)-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

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@@H](OC(=O)[C@@H](CC2=CC=CC=C2)N(C)C1=O)C(C)C)C(C)C

InChI Identifier

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+/m1/s1

InChI Key

GYSCAQFHASJXRS-WXWJZEDASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cordyceps polyarthra	LOTUS Database	35616633
Cordyceps tenuipes	LOTUS Database	35616633
Fusarium incarnatum	LOTUS Database	35616633
Fusarium subglutinans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.27	ChemAxon
pKa (Strongest Acidic)	18.8	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	139.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	213.47 m³·mol⁻¹	ChemAxon
Polarizability	84.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027924

Chemspider ID

23279163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Beauvericin

METLIN ID

Not Available

PubChem Compound

44419427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Siri-Anusornsak W, Kolawole O, Mahakarnchanakul W, Greer B, Petchkongkaew A, Meneely J, Elliott C, Vangnai K: The Occurrence and Co-Occurrence of Regulated, Emerging, and Masked Mycotoxins in Rice Bran and Maize from Southeast Asia. Toxins (Basel). 2022 Aug 19;14(8). pii: toxins14080567. doi: 10.3390/toxins14080567. [PubMed:36006229 ]
Fliszar-Nyul E, Faisal Z, Skaper R, Lemli B, Bayartsetseg B, Hetenyi C, Gombos P, Szabo A, Poor M: Interaction of the Emerging Mycotoxins Beauvericin, Cyclopiazonic Acid, and Sterigmatocystin with Human Serum Albumin. Biomolecules. 2022 Aug 11;12(8):1106. doi: 10.3390/biom12081106. [PubMed:36009000 ]
Alonso-Garrido M, Lozano M, Riffo-Campos AL, Font G, Vila-Donat P, Manyes L: Assessment of single-nucleotide variant discovery protocols in RNA-seq data from human cells exposed to mycotoxins. Toxicol Mech Methods. 2023 Mar;33(3):215-221. doi: 10.1080/15376516.2022.2117673. Epub 2022 Sep 1. [PubMed:36016515 ]
Rana S, Singh SK, Dufosse L: Multigene Phylogeny, Beauvericin Production and Bioactive Potential of Fusarium Strains Isolated in India. J Fungi (Basel). 2022 Jun 24;8(7):662. doi: 10.3390/jof8070662. [PubMed:35887419 ]
Yuan Y, Meng G, Li Y, Wu C: Study on In Vitro Metabolism and In Vivo Pharmacokinetics of Beauvericin. Toxins (Basel). 2022 Jul 12;14(7):477. doi: 10.3390/toxins14070477. [PubMed:35878215 ]
LOTUS database [Link]

Showing NP-Card for (3r,6s,9r,12s,15r,18s)-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 (NP0199700)

MOL for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

3D MOL for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

3D SDF for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

3D-SDF for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

PDB for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

3D PDB for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

SMILES for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

INCHI for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

Structure for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)

3D Structure for NP0199700 ((3r,6s,9r,12s,15r,18s)-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)