NP-MRD: Showing NP-Card for Bactobolin (NP0021578)

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Record Information

Version

2.0

Created at

2021-01-06 06:51:57 UTC

Updated at

2021-07-15 17:36:43 UTC

NP-MRD ID

NP0021578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bactobolin

Provided By

NPAtlas

Description

Bactobolin is found in Pseudomonas. Bactobolin was first documented in 1979 (PMID: 528370). Based on a literature review very few articles have been published on (2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-2-benzopyran-4-yl]-2-aminopropanimidic acid (PMID: 20095633) (PMID: 33540653) (PMID: 33052546) (PMID: 32285674) (PMID: 32105069) (PMID: 31324628).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105163D          

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M  END
> <DATABASE_ID>
NP0021578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)O[C@](C([H])([H])[H])(C([H])(Cl)Cl)[C@]([H])(N([H])C(=O)[C@@]([H])(N([H])[H])C([H])([H])[H])[C@]2([H])[C@@]([H])(O[H])[C@]([H])(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1

> <INCHI_KEY>
RBCHRRIVFAIGFI-RGBMRXMBSA-N

> <FORMULA>
C14H20Cl2N2O6

> <MOLECULAR_WEIGHT>
383.22

> <EXACT_MASS>
382.0698418

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.365258371544215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-2-benzopyran-4-yl]-2-aminopropanamide

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-1.849302008840486

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.04433115607877

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.031039358366025

> <JCHEM_PKA_STRONGEST_BASIC>
8.21138149979168

> <JCHEM_POLAR_SURFACE_AREA>
142.11

> <JCHEM_REFRACTIVITY>
86.188

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-2-benzopyran-4-yl]-2-aminopropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    3.5435   -1.4069   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749   -0.2427   -0.1555 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6405   -0.6680    0.8376 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    0.0643    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672   -0.0849    1.7125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    0.5022   -0.3078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.7854    0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9858   -0.3241    0.1221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3894    0.0491    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741   -0.9251    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5970   -0.6255    0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720   -2.3155    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -2.2749   -1.1213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5217   -2.4520   -2.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402   -1.0266   -1.1836 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3359   -1.3282   -1.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    1.4312    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    1.6749    1.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    2.4196    0.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    2.1720    0.1480 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0799    3.0742    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258    2.8248   -1.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6911    4.4764   -1.1367 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    3.0740   -0.9706 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -1.9139   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -2.1495   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082   -1.0965   -2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146    0.6444   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6101   -0.4573    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -1.7151    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048    0.6103   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220    0.7091    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7766   -1.1445    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3178   -0.9331   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -2.9126   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -2.7661    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -3.1325   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527   -2.7114   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101   -0.3517   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -1.6390   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    2.5423    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582    3.1607    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347    4.0377    1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828    2.3451   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  1  0
 20  7  1  0
 15  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  6
  3 29  1  0
  3 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  1
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  1
 14 38  1  0
 15 39  1  6
 16 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  6
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.543  -1.407  -1.142  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.675  -0.243  -0.156  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.641  -0.668   0.838  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.357   0.064   0.454  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.267  -0.085   1.712  0.00  0.00           O+0
HETATM    6  N   UNK     0       1.242   0.502  -0.308  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.020   0.785   0.354  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.986  -0.324   0.122  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.389   0.049   0.376  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.274  -0.925   0.329  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.597  -0.626   0.561  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.772  -2.316   0.020  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.792  -2.275  -1.121  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.522  -2.452  -2.308  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.940  -1.027  -1.184  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.336  -1.328  -1.656  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.712   1.431   0.649  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.785   1.675   1.309  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.863   2.420   0.193  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.487   2.172   0.148  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.080   3.074   1.275  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.026   2.825  -1.123  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      -0.691   4.476  -1.137  0.00  0.00          Cl+0
HETATM   24 Cl   UNK     0       1.786   3.074  -0.971  0.00  0.00          Cl+0
HETATM   25  H   UNK     0       4.539  -1.914  -1.255  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.883  -2.150  -0.622  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.108  -1.097  -2.093  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.115   0.644  -0.661  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.610  -0.457   0.484  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.556  -1.715   0.957  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.405   0.610  -1.335  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.222   0.709   1.469  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.777  -1.145   0.897  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.318  -0.933  -0.053  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.683  -2.913  -0.237  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.338  -2.766   0.933  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.068  -3.132  -1.020  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.453  -2.711  -2.126  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.410  -0.352  -1.954  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.222  -1.639  -2.590  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.178   2.542   2.222  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.158   3.161   1.124  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.435   4.038   1.276  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.283   2.345  -2.044  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3    4   28                                             
CONECT    3    2   29   30                                                  
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   31                                                  
CONECT    7    6    8   20   32                                             
CONECT    8    7    9   15   33                                             
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   34                                                       
CONECT   12   10   13   35   36                                             
CONECT   13   12   14   15   37                                             
CONECT   14   13   38                                                       
CONECT   15   13   16    8   39                                             
CONECT   16   15   40                                                       
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22    7                                             
CONECT   21   20   41   42   43                                             
CONECT   22   20   23   24   44                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
    3.5435   -1.4069   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749   -0.2427   -0.1555 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6405   -0.6680    0.8376 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    0.0643    0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672   -0.0849    1.7125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    0.5022   -0.3078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.7854    0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9858   -0.3241    0.1221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3894    0.0491    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741   -0.9251    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5970   -0.6255    0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720   -2.3155    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -2.2749   -1.1213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5217   -2.4520   -2.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9402   -1.0266   -1.1836 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3359   -1.3282   -1.6555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    1.4312    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7855    1.6749    1.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631    2.4196    0.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    2.1720    0.1480 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0799    3.0742    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0258    2.8248   -1.1234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6911    4.4764   -1.1367 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    3.0740   -0.9706 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5387   -1.9139   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -2.1495   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082   -1.0965   -2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146    0.6444   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6101   -0.4573    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5563   -1.7151    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048    0.6103   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220    0.7091    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7766   -1.1445    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3178   -0.9331   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -2.9126   -0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -2.7661    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -3.1325   -1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527   -2.7114   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4101   -0.3517   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -1.6390   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    2.5423    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582    3.1607    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347    4.0377    1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828    2.3451   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  9 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  1  0
 20  7  1  0
 15  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  6
  3 29  1  0
  3 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  1
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  1
 14 38  1  0
 15 39  1  6
 16 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-N-[(3S,4R,4AR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-2-benzopyran-4-yl]-2-aminopropanimidate	Generator
BN 183b	MeSH
BN-183b	MeSH
Bactobolin hydrochloride, (s*)-isomer	MeSH
(3S,4R,4AR,5R,6R)-4-(L-alanylamino)-3-(dichloromethyl)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1H-2-oxa-1-naphthalenone	MeSH
Antibiotic BN 183b	MeSH
Bactobolin hydrochloride, (r*)-isomer	MeSH

Chemical Formula

C₁₄H₂₀Cl₂N₂O₆

Average Mass

383.2200 Da

Monoisotopic Mass

382.06984 Da

IUPAC Name

(2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-2-benzopyran-4-yl]-2-aminopropanamide

Traditional Name

(2S)-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-2-benzopyran-4-yl]-2-aminopropanamide

CAS Registry Number

Not Available

SMILES

C[C@H](N)C(=O)N[C@@H]1[C@@H]2[C@@H](O)[C@H](O)CC(O)=C2C(=O)O[C@]1(C)C(Cl)Cl

InChI Identifier

InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1

InChI Key

RBCHRRIVFAIGFI-RGBMRXMBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pseudomonas	NPAtlas	528370

Species Where Detected

Species Name	Source	Reference
Pseudomonas BMG13-A7	KNApSAcK Database	22123792
Pseudomonas sp. BN-183	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	-0.28	ALOGPS
logP	-1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	142.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.19 m³·mol⁻¹	ChemAxon
Polarizability	35.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005764

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21244596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54676871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Seyedsayamdost MR, Chandler JR, Blodgett JA, Lima PS, Duerkop BA, Oinuma K, Greenberg EP, Clardy J: Quorum-sensing-regulated bactobolin production by Burkholderia thailandensis E264. Org Lett. 2010 Feb 19;12(4):716-9. doi: 10.1021/ol902751x. [PubMed:20095633 ]
Kondo S, Horiuchi Y, Hamada M, Takeuchi T, Umezawa H: A new antitumor antibiotic, bactobolin produced by Pseudomonas. J Antibiot (Tokyo). 1979 Oct;32(10):1069-71. doi: 10.7164/antibiotics.32.1069. [PubMed:528370 ]
Depoorter E, De Canck E, Coenye T, Vandamme P: Burkholderia Bacteria Produce Multiple Potentially Novel Molecules that Inhibit Carbapenem-Resistant Gram-Negative Bacterial Pathogens. Antibiotics (Basel). 2021 Feb 2;10(2). pii: antibiotics10020147. doi: 10.3390/antibiotics10020147. [PubMed:33540653 ]
Klaus JR, Coulon PML, Koirala P, Seyedsayamdost MR, Deziel E, Chandler JR: Secondary metabolites from the Burkholderia pseudomallei complex: structure, ecology, and evolution. J Ind Microbiol Biotechnol. 2020 Oct;47(9-10):877-887. doi: 10.1007/s10295-020-02317-0. Epub 2020 Oct 14. [PubMed:33052546 ]
Vojackova P, Michalska L, Necas M, Shcherbakov D, Bottger EC, Sponer J, Sponer JE, Svenda J: Stereocontrolled Synthesis of (-)-Bactobolin A. J Am Chem Soc. 2020 Apr 22;142(16):7306-7311. doi: 10.1021/jacs.0c01554. Epub 2020 Apr 14. [PubMed:32285674 ]
Greenberg EP, Chandler JR, Seyedsayamdost MR: The Chemistry and Biology of Bactobolin: A 10-Year Collaboration with Natural Product Chemist Extraordinaire Jon Clardy. J Nat Prod. 2020 Mar 27;83(3):738-743. doi: 10.1021/acs.jnatprod.9b01237. Epub 2020 Feb 27. [PubMed:32105069 ]
Benomar S, Evans KC, Unckless RL, Chandler JR: Efflux Pumps in Chromobacterium Species Increase Antibiotic Resistance and Promote Survival in a Coculture Competition Model. Appl Environ Microbiol. 2019 Sep 17;85(19). pii: AEM.00908-19. doi: 10.1128/AEM.00908-19. Print 2019 Oct 1. [PubMed:31324628 ]
Evans KC, Benomar S, Camuy-Velez LA, Nasseri EB, Wang X, Neuenswander B, Chandler JR: Quorum-sensing control of antibiotic resistance stabilizes cooperation in Chromobacterium violaceum. ISME J. 2018 May;12(5):1263-1272. doi: 10.1038/s41396-018-0047-7. Epub 2018 Jan 26. [PubMed:29374267 ]
Wong RR, Kong C, Lee SH, Nathan S: Detection of Burkholderia pseudomallei toxin-mediated inhibition of protein synthesis using a Caenorhabditis elegans ugt-29 biosensor. Sci Rep. 2016 Jun 7;6:27475. doi: 10.1038/srep27475. [PubMed:27273550 ]
Ojini I, Gammie A: Rapid Identification of Chemoresistance Mechanisms Using Yeast DNA Mismatch Repair Mutants. G3 (Bethesda). 2015 Jul 21;5(9):1925-35. doi: 10.1534/g3.115.020560. [PubMed:26199284 ]
Amunts A, Fiedorczuk K, Truong TT, Chandler J, Greenberg EP, Ramakrishnan V: Bactobolin A binds to a site on the 70S ribosome distinct from previously seen antibiotics. J Mol Biol. 2015 Feb 27;427(4):753-755. doi: 10.1016/j.jmb.2014.12.018. Epub 2015 Jan 3. [PubMed:25562208 ]
Chandler JR, Truong TT, Silva PM, Seyedsayamdost MR, Carr G, Radey M, Jacobs MA, Sims EH, Clardy J, Greenberg EP: Bactobolin resistance is conferred by mutations in the L2 ribosomal protein. mBio. 2012 Dec 18;3(6). pii: mBio.00499-12. doi: 10.1128/mBio.00499-12. [PubMed:23249812 ]
Carr G, Seyedsayamdost MR, Chandler JR, Greenberg EP, Clardy J: Sources of diversity in bactobolin biosynthesis by Burkholderia thailandensis E264. Org Lett. 2011 Jun 17;13(12):3048-51. doi: 10.1021/ol200922s. Epub 2011 May 26. [PubMed:21615115 ]

Showing NP-Card for Bactobolin (NP0021578)

MOL for NP0021578 (Bactobolin)

3D MOL for NP0021578 (Bactobolin)

3D SDF for NP0021578 (Bactobolin)

3D-SDF for NP0021578 (Bactobolin)

PDB for NP0021578 (Bactobolin)

3D PDB for NP0021578 (Bactobolin)

SMILES for NP0021578 (Bactobolin)

INCHI for NP0021578 (Bactobolin)

Structure for NP0021578 (Bactobolin)

3D Structure for NP0021578 (Bactobolin)