NP-MRD: Showing NP-Card for (3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione (NP0303944)

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Record Information

Version

2.0

Created at

2022-09-10 18:41:59 UTC

Updated at

2022-09-10 18:41:59 UTC

NP-MRD ID

NP0303944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione

Description

BZR-cotoxin IV 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. (3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione is found in Bipolaris zeicola. (3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione was first documented in 2016 (PMID: 27277006). Based on a literature review very few articles have been published on BZR-cotoxin IV.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220422D          

 63 65  0  0  1  0            999 V2000
   -3.6462    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598    0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567    1.0947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2400    0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8702    1.8916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 N   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  2  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
   -2.0610    3.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4308    4.8938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0183    5.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933    5.6082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2558    6.3227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8860    7.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9930    7.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7075    8.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2786    9.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2786    8.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2786    5.9248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0754    5.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6588    6.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4557    6.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1181    3.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9431    3.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7056    2.9021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.8806    2.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6671    2.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2504    1.5218    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
  3  4  1  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  4  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  4  0  0  0
 23 25  1  0  0  0  0
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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
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 32 33  1  0  0  0  0
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 61 62  1  0  0  0  0
  5 62  1  0  0  0  0
 62 63  2  0  0  0  0
M  END

     RDKit          3D

132134  0  0  0  0  0  0  0  0999 V2000
    6.7271    4.3089   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3837    3.6082    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.2321   -0.5560 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6747    2.2417   -2.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1431    1.4669   -0.2363 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0242   -0.9059   -1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4052   -1.2508   -2.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5493   -2.0851   -0.3066 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1233   -2.1246    1.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2630   -3.4138    1.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3918   -2.2982    1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102220422D          

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M  END
> <DATABASE_ID>
NP0303944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@@H](C)N=C(O)CN=C(O)[C@@H](N=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@H](CC(C)C)N(C)C(=O)[C@@H](OC1=O)C(C)C)[C@@H](C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C47H69N7O9/c1-11-29(7)38-45(60)48-26-37(55)49-31(9)41(56)50-34(24-32-19-15-13-16-20-32)43(58)53-39(30(8)12-2)47(62)63-40(28(5)6)46(61)54(10)36(23-27(3)4)44(59)51-35(42(57)52-38)25-33-21-17-14-18-22-33/h13-22,27-31,34-36,38-40H,11-12,23-26H2,1-10H3,(H,48,60)(H,49,55)(H,50,56)(H,51,59)(H,52,57)(H,53,58)/t29-,30-,31+,34-,35-,36-,38-,39-,40-/m0/s1

> <INCHI_KEY>
HYRIAKASPMEAMO-VKJNQXOZSA-N

> <FORMULA>
C47H69N7O9

> <MOLECULAR_WEIGHT>
876.109

> <EXACT_MASS>
875.51567683

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
93.88646984436674

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,9R,15S,18S,21S,24S)-6,18-dibenzyl-3,15-bis[(2S)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-9,22-dimethyl-21-(2-methylpropyl)-24-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione

> <JCHEM_LOGP>
9.127931096333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.620428176847179

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1807032953844083

> <JCHEM_PKA_STRONGEST_BASIC>
1.7579502049771485

> <JCHEM_POLAR_SURFACE_AREA>
242.14999999999995

> <JCHEM_REFRACTIVITY>
239.06280000000018

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,9R,15S,18S,21S,24S)-6,18-dibenzyl-3,15-bis[(2S)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.806   0.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.205   1.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.692   2.044   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.781   0.955   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.091   3.531   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -8.002   4.620   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -5.335   6.160   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -3.847   6.559   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.758   5.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.449   8.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.961   8.445   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -4.538   9.135   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -3.768  10.469   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.228  10.469   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.538  11.802   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -6.078  11.802   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -6.476  13.290   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.387  14.379   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -7.964  13.689   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.362  15.176   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.850  15.575   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.273  16.265   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.672  17.753   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -9.053  12.600   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0     -10.386  13.370   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -10.386  14.910   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -11.720  12.600   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -13.054  13.370   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -13.054  14.910   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.387  15.680   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -14.387  17.220   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.054  17.990   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.720  17.220   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.720  15.680   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0     -11.720  11.060   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0     -13.207  10.661   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -14.296  11.750   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -13.606   9.173   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -15.094   8.775   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -16.183   9.864   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -17.670   9.465   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -15.784  11.351   0.000  0.00  0.00           C+0
HETATM   53  N   UNK     0     -12.517   8.085   0.000  0.00  0.00           N+0
HETATM   54  C   UNK     0     -10.990   8.286   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -13.287   6.751   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -14.827   6.751   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -12.517   5.417   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -13.287   4.083   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -12.517   2.750   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -14.827   4.083   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -10.977   5.417   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0     -10.579   3.930   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0     -11.667   2.841   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   62                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    9   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   45                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   37   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   48   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   61                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   57   62                                                       
CONECT   62   61    5   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₆₉N₇O₉

Average Mass

876.1090 Da

Monoisotopic Mass

875.51568 Da

IUPAC Name

(3S,6S,9R,15S,18S,21S,24S)-6,18-dibenzyl-3,15-bis[(2S)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-9,22-dimethyl-21-(2-methylpropyl)-24-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione

Traditional Name

(3S,6S,9R,15S,18S,21S,24S)-6,18-dibenzyl-3,15-bis[(2S)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@@H](C)N=C(O)CN=C(O)[C@@H](N=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@H](CC(C)C)N(C)C(=O)[C@@H](OC1=O)C(C)C)[C@@H](C)CC

InChI Identifier

InChI=1S/C47H69N7O9/c1-11-29(7)38-45(60)48-26-37(55)49-31(9)41(56)50-34(24-32-19-15-13-16-20-32)43(58)53-39(30(8)12-2)47(62)63-40(28(5)6)46(61)54(10)36(23-27(3)4)44(59)51-35(42(57)52-38)25-33-21-17-14-18-22-33/h13-22,27-31,34-36,38-40H,11-12,23-26H2,1-10H3,(H,48,60)(H,49,55)(H,50,56)(H,51,59)(H,52,57)(H,53,58)/t29-,30-,31+,34-,35-,36-,38-,39-,40-/m0/s1

InChI Key

HYRIAKASPMEAMO-VKJNQXOZSA-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
Bipolaris zeicola	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
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
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	9.13	ChemAxon
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	1.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	242.15 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	239.06 m³·mol⁻¹	ChemAxon
Polarizability	93.89 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

78441285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ali L, Khan AL, Hussain J, Al-Harrasi A, Waqas M, Kang SM, Al-Rawahi A, Lee IJ: Sorokiniol: a new enzymes inhibitory metabolite from fungal endophyte Bipolaris sorokiniana LK12. BMC Microbiol. 2016 Jun 9;16:103. doi: 10.1186/s12866-016-0722-7. [PubMed:27277006 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione (NP0303944)

MOL for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

3D MOL for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

3D SDF for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

3D-SDF for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

PDB for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

3D PDB for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

SMILES for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

INCHI for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

Structure for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)

3D Structure for NP0303944 ((3s,6s,9r,15s,18s,21s,24s)-6,18-dibenzyl-3,15-bis[(2s)-butan-2-yl]-5,8,11,14,17,20-hexahydroxy-24-isopropyl-9,22-dimethyl-21-(2-methylpropyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclotetracosa-4,7,10,13,16,19-hexaene-2,23-dione)