MiMeDB: Showing metabocard for Ferric enterobactin (MMDBc0031680)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:44:06 UTC

Update Date

2022-08-31 18:23:05 UTC

Metabolite ID

MMDBc0031680

Metabolite Identification

Common Name

Ferric enterobactin

Description

Ferric enterobactin is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. Ferric enterobactin is a catecholate siderophore that binds with high affinity (Kd approximately 10-10 M) to the Escherichia coli outer membrane protein FepA. (PMID 10998164 ) The Escherichia coli FepA protein is an energy- and TonB-dependent, ligand-binding porin that functions as a receptor for the siderophore ferric enterobactin and colicins B and D. (PMID 9268330 ) The periplasmic protein FepB of Escherichia coli is a component of the ferric enterobactin transport system. (PMID 10986237 ) The ferric enterobactin receptor, FepA, is a TonB-dependent gated porin that transports the siderophore ferric enterobactin across the outer membrane of gram-negative bacteria. (PMID 7947735 ) In Escherichia coli, the outer membrane protein FepA is a receptor for the siderophore complex ferric enterobactin and for colicins B and D. (PMID 2201687 ) FepA is an Escherichia coli outer membrane receptor protein for the siderophore ferric enterobactin. (PMID 7504275 ) FepA is the Escherichia coli outer membrane receptor for ferric enterobactin, colicin D and colicin B. (PMID 11532122 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 07301213482D          

 49 51  0  0  0  0            999 V2000
   -3.6319    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -3.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -4.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -3.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    0.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    0.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    4.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -4.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    2.7844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -1.7531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -0.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    0.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    1.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    1.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3487    0.0000    0.0000 Fe  0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19  7  2  0  0  0  0
 20  8  2  0  0  0  0
 21  9  2  0  0  0  0
 22 13  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 23 20  1  0  0  0  0
 24 15  2  0  0  0  0
 24 21  1  0  0  0  0
 25 13  1  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 18  1  0  0  0  0
 30 17  1  0  0  0  0
 31 16  1  4  0  0  0
 31 25  2  0  0  0  0
 32 17  1  4  0  0  0
 32 26  2  0  0  0  0
 33 18  1  4  0  0  0
 33 27  2  0  0  0  0
 34 19  1  0  0  0  0
 35 20  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 40 25  1  0  0  0  0
 41 26  1  0  0  0  0
 42 27  1  0  0  0  0
 43 28  1  0  0  0  0
 44 29  1  0  0  0  0
 45 30  1  0  0  0  0
 46 10  1  0  0  0  0
 46 29  1  0  0  0  0
 47 11  1  0  0  0  0
 47 28  1  0  0  0  0
 48 12  1  0  0  0  0
 48 30  1  0  0  0  0
M  END


  Mrv0541 07301213482D          

 49 51  0  0  0  0            999 V2000
   -3.6319    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -3.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -4.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -2.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    0.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    1.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -3.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740   -2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    0.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595   -1.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    0.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    4.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -4.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    2.7844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885    3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7740    1.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -1.7531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839   -0.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    0.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    1.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549   -2.1656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    1.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4885   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3487    0.0000    0.0000 Fe  0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19  7  2  0  0  0  0
 20  8  2  0  0  0  0
 21  9  2  0  0  0  0
 22 13  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 23 20  1  0  0  0  0
 24 15  2  0  0  0  0
 24 21  1  0  0  0  0
 25 13  1  0  0  0  0
 26 14  1  0  0  0  0
 27 15  1  0  0  0  0
 28 16  1  0  0  0  0
 29 18  1  0  0  0  0
 30 17  1  0  0  0  0
 31 16  1  4  0  0  0
 31 25  2  0  0  0  0
 32 17  1  4  0  0  0
 32 26  2  0  0  0  0
 33 18  1  4  0  0  0
 33 27  2  0  0  0  0
 34 19  1  0  0  0  0
 35 20  1  0  0  0  0
 36 21  1  0  0  0  0
 37 22  1  0  0  0  0
 38 23  1  0  0  0  0
 39 24  1  0  0  0  0
 40 25  1  0  0  0  0
 41 26  1  0  0  0  0
 42 27  1  0  0  0  0
 43 28  1  0  0  0  0
 44 29  1  0  0  0  0
 45 30  1  0  0  0  0
 46 10  1  0  0  0  0
 46 29  1  0  0  0  0
 47 11  1  0  0  0  0
 47 28  1  0  0  0  0
 48 12  1  0  0  0  0
 48 30  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031680

> <DATABASE_NAME>
MIME

> <SMILES>
[Fe].OC1OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC1N=C(O)C1=C(O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H33N3O15.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;/h1-9,16-18,28-30,34-39,43-45H,10-12H2,(H,31,40)(H,32,41)(H,33,42);

> <INCHI_KEY>
WPYKFMKTUGWUGY-UHFFFAOYSA-N

> <FORMULA>
C30H33FeN3O15

> <MOLECULAR_WEIGHT>
731.439

> <EXACT_MASS>
731.126109534

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
65.12106446278017

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzene-1-carboximidic acid iron

> <JCHEM_LOGP>
4.161235009

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.947650277493416

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.537796458759956

> <JCHEM_PKA_STRONGEST_BASIC>
-6.323186827320691

> <JCHEM_POLAR_SURFACE_AREA>
307.53000000000003

> <JCHEM_REFRACTIVITY>
162.87360000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid iron

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49 Fe   UNK     0       0.000   0.000   0.000  0.00  0.00          Fe+0
CONECT    1    4    7                                                       
CONECT    2    5    8                                                       
CONECT    3    6    9                                                       
CONECT    4    1   13                                                       
CONECT    5    2   14                                                       
CONECT    6    3   15                                                       
CONECT    7    1   19                                                       
CONECT    8    2   20                                                       
CONECT    9    3   21                                                       
CONECT   10   16   46                                                       
CONECT   11   17   47                                                       
CONECT   12   18   48                                                       
CONECT   13    4   22   25                                                  
CONECT   14    5   23   26                                                  
CONECT   15    6   24   27                                                  
CONECT   16   10   28   31                                                  
CONECT   17   11   30   32                                                  
CONECT   18   12   29   33                                                  
CONECT   19    7   22   34                                                  
CONECT   20    8   23   35                                                  
CONECT   21    9   24   36                                                  
CONECT   22   13   19   37                                                  
CONECT   23   14   20   38                                                  
CONECT   24   15   21   39                                                  
CONECT   25   13   31   40                                                  
CONECT   26   14   32   41                                                  
CONECT   27   15   33   42                                                  
CONECT   28   16   43   47                                                  
CONECT   29   18   44   46                                                  
CONECT   30   17   45   48                                                  
CONECT   31   16   25                                                       
CONECT   32   17   26                                                       
CONECT   33   18   27                                                       
CONECT   34   19                                                            
CONECT   35   20                                                            
CONECT   36   21                                                            
CONECT   37   22                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   25                                                            
CONECT   41   26                                                            
CONECT   42   27                                                            
CONECT   43   28                                                            
CONECT   44   29                                                            
CONECT   45   30                                                            
CONECT   46   10   29                                                       
CONECT   47   11   28                                                       
CONECT   48   12   30                                                       
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

Synonyms

Not Available

Molecular Formula

C₃₀H₃₃FeN₃O₁₅

Average Mass

731.439

Monoisotopic Mass

731.126109534

IUPAC Name

N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzene-1-carboximidic acid iron

Traditional Name

N-[7,11-bis({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino})-2,6,10-trihydroxy-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzenecarboximidic acid iron

CAS Registry Number

Not Available

SMILES

[Fe].OC1OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC(N=C(O)C2=C(O)C(O)=CC=C2)C(O)OCC1N=C(O)C1=C(O)C(O)=CC=C1

InChI Identifier

InChI=1S/C30H33N3O15.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;/h1-9,16-18,28-30,34-39,43-45H,10-12H2,(H,31,40)(H,32,41)(H,33,42);

InChI Key

WPYKFMKTUGWUGY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylamides

Alternative Parents

Substituents

Salicylamide
Benzamide
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Polyol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic transition metal salt
Organic salt
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	4.16	ChemAxon
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	307.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	162.87 m³·mol⁻¹	ChemAxon
Polarizability	65.12 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-28c8afcd3b5f368a80db	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-28c8afcd3b5f368a80db	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000000900-28c8afcd3b5f368a80db	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-2588cf04e699537c7c41	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000000900-2588cf04e699537c7c41	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0000000900-2588cf04e699537c7c41	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

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	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440956

PDB ID

Not Available

ChEBI ID

Not Available

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 ]

Showing metabocard for Ferric enterobactin (MMDBc0031680)

MOL for #<Metabolite:0x00007fecd8013458>

3D MOL for #<Metabolite:0x00007fecd8013458>

3D SDF for #<Metabolite:0x00007fecd8013458>

3D-SDF for #<Metabolite:0x00007fecd8013458>

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3D PDB for #<Metabolite:0x00007fecd8013458>

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Structure for #<Metabolite:0x00007fecd8013458>

3D Structure for #<Metabolite:0x00007fecd8013458>