MiMeDB: Showing metabocard for ferroxamine minus Fe(3) (MMDBc0031659)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:43:15 UTC

Update Date

2022-08-31 18:22:52 UTC

Metabolite ID

MMDBc0031659

Metabolite Identification

Common Name

ferroxamine minus Fe(3)

Description

Ferrioxamine is catalyzed by fhuF. The phenotype of fhuF mutants and the structural features of the FhuF protein suggest that FhuF is involved in the reduction of ferric iron in cytoplasmic ferrioxamine B. (PMID 9990318 ) Insertional inactivation and gene replacement of both genes showed that while FhuD2 is involved in the transport of iron(III) in complex with ferrichrome, ferrioxamine B, aerobactin, and coprogen, FhuD1 shows a more limited substrate range, capable of only iron(III)-ferrichrome and iron(III)-ferrioxamine B transport in S. (PMID 11489851 ) Removal of iron from coprogen, ferrichrome, and ferrioxamine B was significantly lower in fhuF mutants compared to the corresponding parental strains, which suggested that FhuF is involved in iron removal from these hydroxamate-type siderophores. (PMID 14756576 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101207482D          

 40 38  0  0  0  0            999 V2000
   -8.4271   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7126   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7126   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9982   -3.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5692   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8547   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1403   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4258   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -3.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -1.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -0.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    0.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    2.5173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900    2.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189    2.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334    4.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2913    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0057    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7202    4.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334    4.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    2.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -0.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9982   -2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0774    0.0000    0.0000 Fe  0  1  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 23 36  1  0  0  0  0
 16 37  1  0  0  0  0
 11 38  1  0  0  0  0
  4 39  1  0  0  0  0
M  CHG  1  40   3
M  END


  Mrv0541 10101207482D          

 40 38  0  0  0  0            999 V2000
   -8.4271   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7126   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7126   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9982   -3.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5692   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8547   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1403   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4258   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -3.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -3.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -1.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -0.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466    0.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    0.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5755    2.5173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900    2.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189    2.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334    4.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2913    4.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0057    3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7202    4.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334    4.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    2.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -0.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -4.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9982   -2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0774    0.0000    0.0000 Fe  0  1  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 23 36  1  0  0  0  0
 16 37  1  0  0  0  0
 11 38  1  0  0  0  0
  4 39  1  0  0  0  0
M  CHG  1  40   3
M  END
> <DATABASE_ID>
MMDBc0031659

> <DATABASE_NAME>
MIME

> <SMILES>
[Fe+3].CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN

> <INCHI_IDENTIFIER>
InChI=1S/C25H48N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);/q;+3

> <INCHI_KEY>
BLMKUGGNEDBRRA-UHFFFAOYSA-N

> <FORMULA>
C25H48FeN6O8

> <MOLECULAR_WEIGHT>
616.529

> <EXACT_MASS>
616.288304675

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
63.41757194261136

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
iron(3+) ion 3-[(5-aminopentyl)(hydroxy)carbamoyl]-N-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]-C-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid

> <JCHEM_LOGP>
-2.5758867884881806

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
7.514762934767661

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.000430457591999

> <JCHEM_PKA_STRONGEST_BASIC>
10.226542843496604

> <JCHEM_POLAR_SURFACE_AREA>
212.81999999999994

> <JCHEM_REFRACTIVITY>
145.99420000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
iron(3+) ion deferoxamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0     -15.731  -6.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.397  -6.851   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -14.397  -8.391   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0     -13.063  -6.081   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0     -11.730  -6.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.396  -6.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.062  -6.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.728  -6.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.395  -6.851   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -5.061  -6.081   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -3.727  -6.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.394  -6.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.394  -4.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.060  -3.771   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.274  -4.541   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -1.060  -2.231   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.274  -1.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.274   0.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.607   0.849   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.607   2.389   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.941   3.159   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.941   4.699   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       4.275   5.469   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.275   7.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.608   7.779   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.942   7.009   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.942   5.469   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       8.276   7.779   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       9.609   7.009   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.943   7.779   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.277   7.009   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.610   7.779   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.944   7.009   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      16.278   7.779   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0       8.276   9.319   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.608   4.699   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.394  -1.461   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -3.727  -8.391   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -13.063  -4.541   0.000  0.00  0.00           O+0
HETATM   40 Fe   UNK     0      20.678   0.000   0.000  0.00  0.00          Fe+3
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   39                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   28                                                            
CONECT   36   23                                                            
CONECT   37   16                                                            
CONECT   38   11                                                            
CONECT   39    4                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   76    0
END

Synonyms

Value	Source
Ferrioxamine	MeSH
Ferrioxamine b mesylate	MeSH
Ferrioxamine b, monomethanesulfonate salt	MeSH
Ferrioxamine b, 55fe-labeled	MeSH
Ferrioxamine b	MeSH

Molecular Formula

C₂₅H₄₈FeN₆O₈

Average Mass

616.529

Monoisotopic Mass

616.288304675

IUPAC Name

iron(3+) ion 3-[(5-aminopentyl)(hydroxy)carbamoyl]-N-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]-C-hydroxycarbonimidoyl}propanamido)pentyl]propanimidic acid

Traditional Name

iron(3+) ion deferoxamine

CAS Registry Number

Not Available

SMILES

[Fe+3].CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN

InChI Identifier

InChI=1S/C25H48N6O8.Fe/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26;/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34);/q;+3

InChI Key

BLMKUGGNEDBRRA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Acetamide
Acetohydroxamic acid
Amino acid or derivatives
Carboxamide group
Hydroxamic acid
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic transition metal salt
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic salt
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.6	ChemAxon
pKa (Strongest Acidic)	7	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	212.82 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	145.99 m³·mol⁻¹	ChemAxon
Polarizability	63.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	514.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	409.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	286.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	362.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	285.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	172.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	917.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	1074.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	282.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	203.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	501.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	171.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	154.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	335.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	705.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	109.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	320.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1188.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	731.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	ferroxamine minus Fe(3)_TMS_1	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN)O[Si](C)(C)C	standard non polar	2025-10-24	2566.71
Gas Chromatography	ferroxamine minus Fe(3)_TMS_2	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN)O[Si](C)(C)C	standard non polar	2025-10-24	2596.59
Gas Chromatography	ferroxamine minus Fe(3)_TMS_3	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN[Si](C)(C)C	standard non polar	2025-10-24	1288.32
Gas Chromatography	ferroxamine minus Fe(3)_TMS_4	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1736.06
Gas Chromatography	ferroxamine minus Fe(3)_TMS_5	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2593.02
Gas Chromatography	ferroxamine minus Fe(3)_TMS_6	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1064.11
Gas Chromatography	ferroxamine minus Fe(3)_TMS_7	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1626.77
Gas Chromatography	ferroxamine minus Fe(3)_TMS_8	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1010.95
Gas Chromatography	ferroxamine minus Fe(3)_TMS_9	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2086.69
Gas Chromatography	ferroxamine minus Fe(3)_TMS_10	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	888.685
Gas Chromatography	ferroxamine minus Fe(3)_TMS_11	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2346.73
Gas Chromatography	ferroxamine minus Fe(3)_TMS_1	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN)O[Si](C)(C)C	standard polar	2025-10-24	2523.54
Gas Chromatography	ferroxamine minus Fe(3)_TMS_2	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN)O[Si](C)(C)C	standard polar	2025-10-24	2322.06
Gas Chromatography	ferroxamine minus Fe(3)_TMS_3	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN[Si](C)(C)C	standard polar	2025-10-24	2319.94
Gas Chromatography	ferroxamine minus Fe(3)_TMS_4	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2413.56
Gas Chromatography	ferroxamine minus Fe(3)_TMS_5	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1567.91
Gas Chromatography	ferroxamine minus Fe(3)_TMS_6	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2069.75
Gas Chromatography	ferroxamine minus Fe(3)_TMS_7	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2300.15
Gas Chromatography	ferroxamine minus Fe(3)_TMS_8	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1635.32
Gas Chromatography	ferroxamine minus Fe(3)_TMS_9	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	-197.848
Gas Chromatography	ferroxamine minus Fe(3)_TMS_10	CC(=O)N(O)CCCCCN=C(O)CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1027.44
Gas Chromatography	ferroxamine minus Fe(3)_TMS_11	CC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN=C(CCC(=O)N(O)CCCCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2868.3

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	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

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

441292

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Sebulsky MT, Heinrichs DE: Identification and characterization of fhuD1 and fhuD2, two genes involved in iron-hydroxamate uptake in Staphylococcus aureus. J Bacteriol. 2001 Sep;183(17):4994-5000. doi: 10.1128/JB.183.17.4994-5000.2001. [PubMed:11489851 ]
Matzanke BF, Anemuller S, Schunemann V, Trautwein AX, Hantke K: FhuF, part of a siderophore-reductase system. Biochemistry. 2004 Feb 10;43(5):1386-92. doi: 10.1021/bi0357661. [PubMed:14756576 ]

Showing metabocard for ferroxamine minus Fe(3) (MMDBc0031659)

MOL for #<Metabolite:0x00007f9aba267260>

3D MOL for #<Metabolite:0x00007f9aba267260>

3D SDF for #<Metabolite:0x00007f9aba267260>

3D-SDF for #<Metabolite:0x00007f9aba267260>

PDB for #<Metabolite:0x00007f9aba267260>

3D PDB for #<Metabolite:0x00007f9aba267260>

SMILES for #<Metabolite:0x00007f9aba267260>

INCHI for #<Metabolite:0x00007f9aba267260>

Structure for #<Metabolite:0x00007f9aba267260>

3D Structure for #<Metabolite:0x00007f9aba267260>