MiMeDB: Showing metabocard for Enterochelin (MMDBc0031610)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:19 UTC

Update Date

2024-04-30 19:51:12 UTC

Metabolite ID

MMDBc0031610

Metabolite Identification

Common Name

Enterochelin

Description

Enterobactin (also known as Enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241220592D          

 48 51  0  0  1  0            999 V2000
    7.1670  -18.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1670  -17.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8853  -18.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4556  -18.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8818  -17.0950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522  -17.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8853  -19.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002  -18.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4556  -19.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8818  -16.2667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1703  -19.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002  -19.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5967  -15.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1670  -15.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4522  -14.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3150  -13.7926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4522  -13.7926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7415  -15.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0299  -13.3805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5967  -13.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7415  -13.3805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8818  -12.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5966  -13.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820  -12.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636  -13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  5  1  1  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
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 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
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 30 33  1  0  0  0  0
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 35 39  1  0  0  0  0
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  9 11  2  0  0  0  0
 26 28  1  0  0  0  0
 41 45  1  0  0  0  0
 44 47  2  0  0  0  0
M  END

HMDB0032199
     RDKit          3D
Chymosin preparation, escherichia coli k-12
 75 78  0  0  0  0  0  0  0  0999 V2000
   -2.0687    3.3794   -0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    3.5203    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    2.5611    1.1728 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    1.4023    0.8596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0703    1.5713    1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    2.0047    0.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734    1.5342   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053    2.2283   -1.4486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432    0.2660   -0.5128 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6870    0.5787   -0.0118 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083    0.3985   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -0.0375   -2.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1365    0.7036   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4092    1.1827    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6904    1.4721    1.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363    1.2755    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044    0.7917   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495    0.5878   -1.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2091    0.5158   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    0.0289   -2.5275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -0.7280    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -2.0757    0.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091   -2.9803    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -4.1944    0.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5193   -2.5289    0.5830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3651   -3.7375    0.4439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -3.9189   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -3.0183   -1.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0488   -5.0927   -0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0310   -6.1009    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7882   -7.2404    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6242   -7.4350   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6933   -6.4984   -1.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315   -6.6587   -3.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
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 19 13  1  0
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 42 71  1  0
 43 72  1  0
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 48 75  1  0
M  END


  Mrv0541 02241220592D          

 48 51  0  0  1  0            999 V2000
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   11.4561  -12.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968  -13.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8818  -12.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5966  -13.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820  -12.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636  -13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  5  1  1  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
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 13 15  1  0  0  0  0
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 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 23  1  1  0  0  0
 20 24  1  0  0  0  0
 21 25  1  1  0  0  0
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  9 11  2  0  0  0  0
 26 28  1  0  0  0  0
 41 45  1  0  0  0  0
 44 47  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031610

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1

> <INCHI_KEY>
SERBHKJMVBATSJ-BZSNNMDCSA-N

> <FORMULA>
C30H27N3O15

> <MOLECULAR_WEIGHT>
669.5465

> <EXACT_MASS>
669.144217209

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
61.87430576597656

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
2.2642207240000003

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.299561351870874

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.822545158892101

> <JCHEM_PKA_STRONGEST_BASIC>
-6.328992171650428

> <JCHEM_POLAR_SURFACE_AREA>
287.58

> <JCHEM_REFRACTIVITY>
157.87469999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enterobactin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032199
     RDKit          3D
Chymosin preparation, escherichia coli k-12
 75 78  0  0  0  0  0  0  0  0999 V2000
   -2.0687    3.3794   -0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7516    7.6727   -1.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    5.6213   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1981    5.5380   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2126    2.4300    2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7344   -7.9951    0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
  2  3  1  0
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 19 13  1  0
 35 29  1  0
  3 49  1  0
  4 50  1  6
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 42 71  1  0
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 44 73  1  0
 46 74  1  0
 48 75  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.378 -34.227   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.378 -32.681   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.719 -34.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.050 -34.983   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      14.713 -31.911   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      12.044 -31.911   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.719 -36.523   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.054 -34.214   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.050 -36.523   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.713 -30.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.385 -37.299   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.054 -37.299   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.047 -29.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.378 -29.602   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.047 -28.062   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      17.388 -30.365   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      13.378 -28.062   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      17.388 -27.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.044 -27.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.388 -25.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.044 -25.746   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.717 -28.062   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      18.723 -24.977   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      16.047 -24.977   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      10.717 -24.977   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      13.378 -24.977   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.057 -25.746   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.713 -25.746   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.047 -23.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.376 -25.746   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.391 -24.977   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      20.057 -27.286   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.042 -24.977   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.376 -27.286   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      22.711 -25.740   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.385 -23.431   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.714 -25.752   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.048 -23.444   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      24.046 -24.977   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      22.711 -27.286   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      22.711 -22.661   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.380 -24.983   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.720 -27.292   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       6.714 -22.667   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      24.046 -23.431   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      25.380 -25.740   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       5.380 -23.444   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       4.039 -25.752   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2                                                            
CONECT    7    3   11   12                                                  
CONECT    8    3                                                            
CONECT    9    4   11                                                       
CONECT   10    5   13   14                                                  
CONECT   11    7    9                                                       
CONECT   12    7                                                            
CONECT   13   10   15   16                                                  
CONECT   14   10   17                                                       
CONECT   15   13   18                                                       
CONECT   16   13                                                            
CONECT   17   14   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   21   22                                                  
CONECT   20   18   23   24                                                  
CONECT   21   19   25   26                                                  
CONECT   22   19                                                            
CONECT   23   20   27                                                       
CONECT   24   20   28   29                                                  
CONECT   25   21   30                                                       
CONECT   26   21   28                                                       
CONECT   27   23   31   32                                                  
CONECT   28   24   26                                                       
CONECT   29   24                                                            
CONECT   30   25   33   34                                                  
CONECT   31   27   35   36                                                  
CONECT   32   27                                                            
CONECT   33   30   37   38                                                  
CONECT   34   30                                                            
CONECT   35   31   39   40                                                  
CONECT   36   31   41                                                       
CONECT   37   33   42   43                                                  
CONECT   38   33   44                                                       
CONECT   39   35   45   46                                                  
CONECT   40   35                                                            
CONECT   41   36   45                                                       
CONECT   42   37   47   48                                                  
CONECT   43   37                                                            
CONECT   44   38   47                                                       
CONECT   45   39   41                                                       
CONECT   46   39                                                            
CONECT   47   42   44                                                       
CONECT   48   42                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

COMPND    HMDB0032199
HETATM    1  O1  UNL     1      -2.069   3.379  -0.992  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.532   3.520   0.177  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.231   2.561   1.173  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.382   1.402   0.860  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.070   1.571   1.542  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.969   2.005   0.734  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.573   1.534  -0.368  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.505   2.228  -1.449  1.00  0.00           O  
HETATM    9  C5  UNL     1       2.343   0.266  -0.513  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.687   0.579  -0.012  1.00  0.00           N  
HETATM   11  C6  UNL     1       4.808   0.399  -0.858  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.654  -0.038  -2.051  1.00  0.00           O  
HETATM   13  C7  UNL     1       6.136   0.704  -0.387  1.00  0.00           C  
HETATM   14  C8  UNL     1       6.409   1.183   0.867  1.00  0.00           C  
HETATM   15  C9  UNL     1       7.690   1.472   1.288  1.00  0.00           C  
HETATM   16  C10 UNL     1       8.736   1.276   0.425  1.00  0.00           C  
HETATM   17  C11 UNL     1       8.504   0.792  -0.854  1.00  0.00           C  
HETATM   18  O5  UNL     1       9.549   0.588  -1.737  1.00  0.00           O  
HETATM   19  C12 UNL     1       7.209   0.516  -1.233  1.00  0.00           C  
HETATM   20  O6  UNL     1       6.997   0.029  -2.528  1.00  0.00           O  
HETATM   21  C13 UNL     1       1.731  -0.728   0.429  1.00  0.00           C  
HETATM   22  O7  UNL     1       1.913  -2.076   0.036  1.00  0.00           O  
HETATM   23  C14 UNL     1       0.909  -2.980   0.409  1.00  0.00           C  
HETATM   24  O8  UNL     1       1.198  -4.194   0.605  1.00  0.00           O  
HETATM   25  C15 UNL     1      -0.519  -2.529   0.583  1.00  0.00           C  
HETATM   26  N3  UNL     1      -1.365  -3.737   0.444  1.00  0.00           N  
HETATM   27  C16 UNL     1      -2.218  -3.919  -0.645  1.00  0.00           C  
HETATM   28  O9  UNL     1      -2.238  -3.018  -1.504  1.00  0.00           O  
HETATM   29  C17 UNL     1      -3.049  -5.093  -0.785  1.00  0.00           C  
HETATM   30  C18 UNL     1      -3.031  -6.101   0.192  1.00  0.00           C  
HETATM   31  C19 UNL     1      -3.788  -7.240   0.142  1.00  0.00           C  
HETATM   32  C20 UNL     1      -4.624  -7.435  -0.917  1.00  0.00           C  
HETATM   33  C21 UNL     1      -4.693  -6.498  -1.904  1.00  0.00           C  
HETATM   34  O10 UNL     1      -5.531  -6.659  -3.000  1.00  0.00           O  
HETATM   35  C22 UNL     1      -3.914  -5.333  -1.844  1.00  0.00           C  
HETATM   36  O11 UNL     1      -4.021  -4.423  -2.864  1.00  0.00           O  
HETATM   37  C23 UNL     1      -0.744  -1.856   1.892  1.00  0.00           C  
HETATM   38  O12 UNL     1      -1.742  -0.883   1.944  1.00  0.00           O  
HETATM   39  C24 UNL     1      -2.108   0.141   1.147  1.00  0.00           C  
HETATM   40  O13 UNL     1      -3.235   0.061   0.529  1.00  0.00           O  
HETATM   41  C25 UNL     1      -3.368   4.685   0.441  1.00  0.00           C  
HETATM   42  C26 UNL     1      -3.908   4.895   1.706  1.00  0.00           C  
HETATM   43  C27 UNL     1      -4.692   5.987   1.961  1.00  0.00           C  
HETATM   44  C28 UNL     1      -4.970   6.903   0.982  1.00  0.00           C  
HETATM   45  C29 UNL     1      -4.467   6.745  -0.275  1.00  0.00           C  
HETATM   46  O14 UNL     1      -4.752   7.673  -1.252  1.00  0.00           O  
HETATM   47  C30 UNL     1      -3.661   5.621  -0.529  1.00  0.00           C  
HETATM   48  O15 UNL     1      -3.198   5.538  -1.810  1.00  0.00           O  
HETATM   49  H1  UNL     1      -2.588   2.644   2.120  1.00  0.00           H  
HETATM   50  H2  UNL     1      -1.160   1.503  -0.236  1.00  0.00           H  
HETATM   51  H3  UNL     1      -0.213   2.430   2.277  1.00  0.00           H  
HETATM   52  H4  UNL     1       0.211   0.751   2.244  1.00  0.00           H  
HETATM   53  H5  UNL     1       2.369  -0.066  -1.551  1.00  0.00           H  
HETATM   54  H6  UNL     1       3.706   0.922   0.965  1.00  0.00           H  
HETATM   55  H7  UNL     1       5.569   1.339   1.557  1.00  0.00           H  
HETATM   56  H8  UNL     1       7.871   1.844   2.271  1.00  0.00           H  
HETATM   57  H9  UNL     1       9.761   1.497   0.732  1.00  0.00           H  
HETATM   58  H10 UNL     1      10.516   0.773  -1.511  1.00  0.00           H  
HETATM   59  H11 UNL     1       7.762  -0.118  -3.170  1.00  0.00           H  
HETATM   60  H12 UNL     1       2.105  -0.533   1.430  1.00  0.00           H  
HETATM   61  H13 UNL     1       0.627  -0.558   0.305  1.00  0.00           H  
HETATM   62  H14 UNL     1      -0.784  -1.883  -0.274  1.00  0.00           H  
HETATM   63  H15 UNL     1      -1.302  -4.453   1.191  1.00  0.00           H  
HETATM   64  H16 UNL     1      -2.381  -5.979   1.045  1.00  0.00           H  
HETATM   65  H17 UNL     1      -3.734  -7.995   0.934  1.00  0.00           H  
HETATM   66  H18 UNL     1      -5.245  -8.351  -0.975  1.00  0.00           H  
HETATM   67  H19 UNL     1      -5.555  -5.951  -3.704  1.00  0.00           H  
HETATM   68  H20 UNL     1      -3.578  -3.581  -3.005  1.00  0.00           H  
HETATM   69  H21 UNL     1      -1.150  -2.689   2.568  1.00  0.00           H  
HETATM   70  H22 UNL     1       0.201  -1.595   2.419  1.00  0.00           H  
HETATM   71  H23 UNL     1      -3.692   4.180   2.474  1.00  0.00           H  
HETATM   72  H24 UNL     1      -5.095   6.119   2.956  1.00  0.00           H  
HETATM   73  H25 UNL     1      -5.606   7.756   1.258  1.00  0.00           H  
HETATM   74  H26 UNL     1      -4.364   7.534  -2.187  1.00  0.00           H  
HETATM   75  H27 UNL     1      -2.653   4.951  -2.334  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   41
CONECT    3    4   49
CONECT    4    5   39   50
CONECT    5    6   51   52
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   21   53
CONECT   10   11   54
CONECT   11   12   12   13
CONECT   13   14   14   19
CONECT   14   15   55
CONECT   15   16   16   56
CONECT   16   17   57
CONECT   17   18   19   19
CONECT   18   58
CONECT   19   20
CONECT   20   59
CONECT   21   22   60   61
CONECT   22   23
CONECT   23   24   24   25
CONECT   25   26   37   62
CONECT   26   27   63
CONECT   27   28   28   29
CONECT   29   30   30   35
CONECT   30   31   64
CONECT   31   32   32   65
CONECT   32   33   66
CONECT   33   34   35   35
CONECT   34   67
CONECT   35   36
CONECT   36   68
CONECT   37   38   69   70
CONECT   38   39
CONECT   39   40   40
CONECT   41   42   42   47
CONECT   42   43   71
CONECT   43   44   44   72
CONECT   44   45   73
CONECT   45   46   47   47
CONECT   46   74
CONECT   47   48
CONECT   48   75
END

HMDB0032199
     RDKit          3D
Chymosin preparation, escherichia coli k-12
 75 78  0  0  0  0  0  0  0  0999 V2000
   -2.0687    3.3794   -0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    3.5203    0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2309    2.5611    1.1728 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822    1.4023    0.8596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0703    1.5713    1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    2.0047    0.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734    1.5342   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5053    2.2283   -1.4486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432    0.2660   -0.5128 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6870    0.5787   -0.0118 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083    0.3985   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -0.0375   -2.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1365    0.7036   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4092    1.1827    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6904    1.4721    1.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7363    1.2755    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044    0.7917   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495    0.5878   -1.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2091    0.5158   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972    0.0289   -2.5275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -0.7280    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -2.0757    0.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091   -2.9803    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -4.1944    0.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5193   -2.5289    0.5830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3651   -3.7375    0.4439 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -3.9189   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -3.0183   -1.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0488   -5.0927   -0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0310   -6.1009    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7882   -7.2404    0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6242   -7.4350   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6933   -6.4984   -1.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5315   -6.6587   -3.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135   -5.3333   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0207   -4.4228   -2.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444   -1.8565    1.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418   -0.8834    1.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078    0.1406    1.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2349    0.0609    0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    4.6848    0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    4.8954    1.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6921    5.9868    1.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9696    6.9030    0.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666    6.7453   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7516    7.6727   -1.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    5.6213   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1981    5.5380   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875    2.6438    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.5027   -0.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    2.4300    2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112    0.7508    2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -0.0658   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7062    0.9220    0.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5686    1.3389    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8705    1.8441    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7606    1.4971    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5155    0.7731   -1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615   -0.1177   -3.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -0.5330    1.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274   -0.5577    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -1.8834   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3016   -4.4531    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808   -5.9792    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344   -7.9951    0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2454   -8.3513   -0.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5546   -5.9508   -3.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5779   -3.5814   -3.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -2.6894    2.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2006   -1.5946    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918    4.1797    2.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0952    6.1191    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064    7.7559    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3644    7.5338   -2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6529    4.9515   -2.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 25 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
  2 41  1  0
 41 42  2  0
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 39  4  1  0
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 19 13  1  0
 35 29  1  0
  3 49  1  0
  4 50  1  6
  5 51  1  0
  5 52  1  0
  9 53  1  6
 10 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 18 58  1  0
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 21 60  1  0
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 30 64  1  0
 31 65  1  0
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 34 67  1  0
 36 68  1  0
 37 69  1  0
 37 70  1  0
 42 71  1  0
 43 72  1  0
 44 73  1  0
 46 74  1  0
 48 75  1  0
M  END

Synonyms

Value	Source
(3S-(3R,7R,11R*))-N,n',n''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)	ChEBI
Enterochelin	ChEBI
H6ENT	ChEBI
Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester	ChEBI
Tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester	ChEBI
Enterobactin	Kegg

Molecular Formula

C₃₀H₂₇N₃O₁₅

Average Mass

669.5465

Monoisotopic Mass

669.144217209

IUPAC Name

N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide

Traditional Name

enterobactin

CAS Registry Number

28384-96-5

SMILES

OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1O

InChI Identifier

InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1

InChI Key

SERBHKJMVBATSJ-BZSNNMDCSA-N

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
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Macrolide
Macrolactam
Alpha-amino acid or derivatives
Salicylic acid or derivatives
Salicylamide
Benzamide
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

polyphenol (CHEBI:28855 )
macrocycle (CHEBI:28855 )
crown compound (CHEBI:28855 )
organic aromatic compound (CHEBI:28855 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	1.62	ALOGPS
logP	2.26	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	287.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	157.87 m³·mol⁻¹	ChemAxon
Polarizability	61.87 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0032199

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

34231

PDB ID

EB4

ChEBI ID

28855

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
EAFUS: Everything Added to Food in the United States. [Link]

Showing metabocard for Enterochelin (MMDBc0031610)

MOL for #<Metabolite:0x00007f9252262e60>

3D MOL for #<Metabolite:0x00007f9252262e60>

3D SDF for #<Metabolite:0x00007f9252262e60>

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PDB for #<Metabolite:0x00007f9252262e60>

3D PDB for #<Metabolite:0x00007f9252262e60>

SMILES for #<Metabolite:0x00007f9252262e60>

INCHI for #<Metabolite:0x00007f9252262e60>

Structure for #<Metabolite:0x00007f9252262e60>

3D Structure for #<Metabolite:0x00007f9252262e60>