MiMeDB: Showing metabocard for Fe(III)-enterobactin (MMDBc0054713)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-06 16:33:56 UTC

Update Date

2022-08-12 20:09:03 UTC

Metabolite ID

MMDBc0054713

Metabolite Identification

Common Name

Fe(III)-enterobactin

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07101213122D          
 
 49 51  0  0  1  0            999 V2000
   12.3238  -11.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238  -10.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0421  -12.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6124  -12.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386  -10.5754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6091  -10.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0421  -13.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7570  -11.8093    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.6124  -13.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386   -9.7473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3272  -13.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7570  -13.4621    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.7535   -9.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -9.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -9.7473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -8.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6091   -8.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -7.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6091   -7.2731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8984   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1866   -6.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8984   -6.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9015   -7.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386   -7.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -6.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -7.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6163   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9015   -8.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4652   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -8.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3235   -7.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6128   -6.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7539   -7.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4686   -6.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0384   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3235   -8.0979    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.3235   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390   -6.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7572   -8.1012    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.7539   -5.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0384   -6.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7532   -7.2697    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.0390   -6.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208   -7.2766    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.9158  -11.3047    0.0000 Fe  0  1  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
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 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
 21 26  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  2  0  0  0  0
 25 30  1  0  0  0  0
 27 31  1  0  0  0  0
 27 32  2  0  0  0  0
 30 33  1  0  0  0  0
 30 34  2  0  0  0  0
 31 35  2  0  0  0  0
 31 36  1  0  0  0  0
 33 37  1  0  0  0  0
 33 38  2  0  0  0  0
 35 39  1  0  0  0  0
 35 40  1  0  0  0  0
 36 41  2  0  0  0  0
 37 42  2  0  0  0  0
 37 43  1  0  0  0  0
 38 44  1  0  0  0  0
 39 45  2  0  0  0  0
 39 46  1  0  0  0  0
 42 47  1  0  0  0  0
 42 48  1  0  0  0  0
  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  CHG  7   8  -1  12  -1  40  -1  43  -1  46  -1  48  -1  49   3
M  END

 
  Mrv0541 07101213122D          
 
 49 51  0  0  1  0            999 V2000
   12.3238  -11.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238  -10.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0421  -12.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6124  -12.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386  -10.5754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6091  -10.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0421  -13.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7570  -11.8093    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.6124  -13.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386   -9.7473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3272  -13.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7570  -13.4621    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.7535   -9.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -9.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -9.7473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -8.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6091   -8.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718   -7.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6091   -7.2731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8984   -8.5139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1866   -6.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8984   -6.8611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3238   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9015   -7.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0386   -7.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7535   -6.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -7.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6163   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9015   -8.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4652   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -8.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3235   -7.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6128   -6.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7539   -7.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4686   -6.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0384   -6.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3235   -8.0979    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.3235   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390   -6.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7572   -8.1012    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.7539   -5.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0384   -6.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7532   -7.2697    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.0390   -6.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3208   -7.2766    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.9158  -11.3047    0.0000 Fe  0  1  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
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 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
 21 26  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 24 29  2  0  0  0  0
 25 30  1  0  0  0  0
 27 31  1  0  0  0  0
 27 32  2  0  0  0  0
 30 33  1  0  0  0  0
 30 34  2  0  0  0  0
 31 35  2  0  0  0  0
 31 36  1  0  0  0  0
 33 37  1  0  0  0  0
 33 38  2  0  0  0  0
 35 39  1  0  0  0  0
 35 40  1  0  0  0  0
 36 41  2  0  0  0  0
 37 42  2  0  0  0  0
 37 43  1  0  0  0  0
 38 44  1  0  0  0  0
 39 45  2  0  0  0  0
 39 46  1  0  0  0  0
 42 47  1  0  0  0  0
 42 48  1  0  0  0  0
  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  CHG  7   8  -1  12  -1  40  -1  43  -1  46  -1  48  -1  49   3
M  END
> <DATABASE_ID>
MMDBc0054713

> <DATABASE_NAME>
MIME

> <SMILES>
[Fe+3].[O-]C1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC([O-])=C2[O-])NC(=O)C2=CC=CC([O-])=C2[O-])=C1[O-]

> <INCHI_IDENTIFIER>
InChI=1S/C30H27N3O15.Fe/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);/q;+3/p-6/t16-,17-,18-;/m0./s1

> <INCHI_KEY>
NGILTSZTOFYVBF-UVJOBNTFSA-H

> <FORMULA>
C30H21FeN3O15

> <MOLECULAR_WEIGHT>
719.344

> <EXACT_MASS>
719.03220915

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
60.1335366578373

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
iron(3+) ion 3-{[(3S,7S,11S)-7,11-bis(2,3-dioxidobenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]carbamoyl}benzene-1,2-bis(olate)

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.2642207240000003

> <ALOGPS_LOGS>
-4.34

> <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>
304.56

> <JCHEM_REFRACTIVITY>
221.1764999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iron(3+) ion enterobactin(6-)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-12         0                                  
HETATM    1  C   UNK     0      23.004 -22.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.004 -20.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.345 -22.813   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.677 -22.813   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      24.339 -19.741   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      21.670 -19.741   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      24.345 -24.353   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      25.680 -22.044   0.000  0.00  0.00           O-1
HETATM    9  C   UNK     0      21.677 -24.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.339 -18.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.011 -25.129   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      25.680 -25.129   0.000  0.00  0.00           O-1
HETATM   13  C   UNK     0      25.673 -17.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.004 -17.432   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.673 -15.893   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      27.014 -18.195   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      23.004 -15.893   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      27.014 -15.116   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.670 -15.116   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.014 -13.577   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.670 -13.577   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.344 -15.893   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      28.348 -12.807   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      25.673 -12.807   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      20.344 -12.807   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      23.004 -12.807   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.683 -13.577   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      24.339 -13.577   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      25.673 -11.268   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.003 -13.577   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.017 -12.807   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      29.683 -15.116   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      17.668 -12.807   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      19.003 -15.116   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      32.337 -13.570   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.011 -11.262   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.341 -13.583   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.675 -11.274   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.672 -12.807   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      32.337 -15.116   0.000  0.00  0.00           O-1
HETATM   41  C   UNK     0      32.337 -10.491   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.006 -12.814   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      16.347 -15.122   0.000  0.00  0.00           O-1
HETATM   44  C   UNK     0      16.341 -10.498   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      33.672 -11.262   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      35.006 -13.570   0.000  0.00  0.00           O-1
HETATM   47  C   UNK     0      15.006 -11.274   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      13.665 -13.583   0.000  0.00  0.00           O-1
HETATM   49 Fe   UNK     0      31.576 -21.102   0.000  0.00  0.00          Fe+3
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   49    0  102    0
END

Synonyms

Value	Source
[Fe(ent)](3-)	ChEBI
Fe-enterobactin	ChEBI
Ferrienterobactin	ChEBI

Molecular Formula

C₃₀H₂₁FeN₃O₁₅

Average Mass

719.344

Monoisotopic Mass

719.03220915

IUPAC Name

iron(3+) ion 3-{[(3S,7S,11S)-7,11-bis(2,3-dioxidobenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]carbamoyl}benzene-1,2-bis(olate)

Traditional Name

iron(3+) ion enterobactin(6-)

CAS Registry Number

Not Available

SMILES

[Fe+3].[O-]C1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC([O-])=C2[O-])NC(=O)C2=CC=CC([O-])=C2[O-])=C1[O-]

InChI Identifier

InChI=1S/C30H27N3O15.Fe/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);/q;+3/p-6/t16-,17-,18-;/m0./s1

InChI Key

NGILTSZTOFYVBF-UVJOBNTFSA-H

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organic acids and derivatives

Sub Class

Peptidomimetics

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Alpha-amino acid ester
Macrolactam
Macrolide
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Benzamide
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Phenoxide
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Organoheterocyclic compound
Organic transition metal salt
Carboxylic acid derivative
Oxacycle
Organic salt
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

iron coordination entity (CHEBI:28199 )
organic anion (CHEBI:28199 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2.26	ChemAxon
logS	-4.3	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	3	ChemAxon
Polar Surface Area	304.56 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	221.18 m³·mol⁻¹	ChemAxon
Polarizability	60.13 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

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014964	Fe(III)-enterobactin	Fe(III)-[N-(2,3-dihydroxybenzoyl)-L-serine]	Iron(III) enterobactin esterase	Ester hydrolysis	RHEA	34755880
MMDBr0014965	Fe(III)-enterobactin	Fe(III)-[N-(2,3-dihydroxybenzoyl)-L-serine]	Iron(III) enterobactin esterase	Ester hydrolysis	RHEA	34755880
MMDBr0016932	Adenosine triphosphate	ADP	Ferric enterobactin transport ATP-binding protein FepC	Transport	RHEA	34755880
MMDBr0016933	Adenosine triphosphate	ADP	Ferric enterobactin transport ATP-binding protein FepC	Transport	RHEA	34755880
MMDBr0016986	Fe(III)-enterobactin	Fe(III)-[N-(2,3-dihydroxybenzoyl)-L-serine]3	Iron(III) enterobactin esterase	Ester hydrolysis	RHEA	34755880
MMDBr0016987	Fe(III)-enterobactin	Fe(III)-[N-(2,3-dihydroxybenzoyl)-L-serine]3	Iron(III) enterobactin esterase	Ester hydrolysis	RHEA	34755880

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	Proteobacteria	5	Human ; Human feces

Exposure Sources

Source Type	Source Sub-type	Species	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06230

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16048613

PDB ID

Not Available

ChEBI ID

28199

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Fe(III)-enterobactin (MMDBc0054713)

MOL for #<Metabolite:0x000055c79c192648>

3D MOL for #<Metabolite:0x000055c79c192648>

3D SDF for #<Metabolite:0x000055c79c192648>

3D-SDF for #<Metabolite:0x000055c79c192648>

PDB for #<Metabolite:0x000055c79c192648>

3D PDB for #<Metabolite:0x000055c79c192648>

SMILES for #<Metabolite:0x000055c79c192648>

INCHI for #<Metabolite:0x000055c79c192648>

Structure for #<Metabolite:0x000055c79c192648>

3D Structure for #<Metabolite:0x000055c79c192648>