MiMeDB: Showing metabocard for Ferric coprogen (MMDBc0030162)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:56:22 UTC

Update Date

2022-08-31 17:40:18 UTC

MiMeDB ID

MMDBc0030162

Metabolite Identification

Common Name

Ferric coprogen

Description

Ferric coprogen belongs to the class of Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. (inferred from compound structure)Coprogen is involved in iron transportation. The FhuE protein of Escherichia coli functions as the receptor for ferric coprogen and ferric-rhodotorulic acid. (PMID 3032906 ) The fhuE gene of Escherichia coli encodes the FhuE protein, which is a receptor protein in the coprogen-mediated siderophore iron-transport system. (PMID 16502288 ) 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 ) 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 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05301214522D          

 58 57  0  0  0  0            999 V2000
   -8.9998    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4275    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5764   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0028   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1419    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406    0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0041   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2909   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7172   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2854    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1475   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4262   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2854    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4330   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4262   -0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -0.9408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    3.1842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    1.5342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    2.7717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -0.5283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185   -1.7658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    0.2967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054   -1.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317   -0.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    4.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4330   -3.0033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -0.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    1.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    3.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -3.0033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    1.9467    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.9408    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.7185   -0.9408    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4317   -1.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3625    0.0000    0.0000 Fe  0  1  0  0  0  0  0  0  0  0  0  0
   -8.9998    3.1842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1475   -0.9408    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -2.1783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 23  1  1  0  0  0  0
 23 11  1  0  0  0  0
 23 20  2  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25 13  1  0  0  0  0
 25 22  2  0  0  0  0
 26  4  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 20  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 33 27  1  0  0  0  0
 34 28  1  0  0  0  0
 35 29  1  0  0  0  0
 36 26  2  0  0  0  0
 36 29  1  4  0  0  0
 37 27  1  0  0  0  0
 37 34  2  0  0  0  0
 38 28  1  0  0  0  0
 38 33  2  0  0  0  0
 39 14  1  0  0  0  0
 39 30  1  0  0  0  0
 40 15  1  0  0  0  0
 40 32  1  0  0  0  0
 41 16  1  0  0  0  0
 41 31  1  0  0  0  0
 42 17  1  0  0  0  0
 43 18  1  0  0  0  0
 44 26  1  0  0  0  0
 45 30  2  0  0  0  0
 46 31  2  0  0  0  0
 47 32  2  0  0  0  0
 48 33  1  0  0  0  0
 49 34  1  0  0  0  0
 50 35  2  0  0  0  0
 51 39  1  0  0  0  0
 52 40  1  0  0  0  0
 53 41  1  0  0  0  0
 54 19  1  0  0  0  0
 54 35  1  0  0  0  0
 56 20  1  0  0  0  0
 57 21  1  0  0  0  0
 58 22  1  0  0  0  0
M  CHG  4  51  -1  52  -1  53  -1  55   3
M  END


  Mrv0541 05301214522D          

 58 57  0  0  0  0            999 V2000
   -8.9998    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4275    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5751   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    1.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5764   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0028   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1419    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406    0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0041   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2909   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7172   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2854    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1475   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4262   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2854    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    3.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4330   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4262   -0.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985    1.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    2.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -0.9408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    3.1842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2841    1.5342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    2.7717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -0.5283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185   -1.7658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    0.2967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054   -1.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317   -0.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5709    4.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4330   -3.0033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883   -0.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130    1.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    3.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462   -3.0033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8564    1.9467    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.9408    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.7185   -0.9408    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4317   -1.7658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3625    0.0000    0.0000 Fe  0  1  0  0  0  0  0  0  0  0  0  0
   -8.9998    3.1842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1475   -0.9408    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1406   -2.1783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 23  1  1  0  0  0  0
 23 11  1  0  0  0  0
 23 20  2  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 24 21  2  0  0  0  0
 25  3  1  0  0  0  0
 25 13  1  0  0  0  0
 25 22  2  0  0  0  0
 26  4  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 10  1  0  0  0  0
 30 20  1  0  0  0  0
 31 21  1  0  0  0  0
 32 22  1  0  0  0  0
 33 27  1  0  0  0  0
 34 28  1  0  0  0  0
 35 29  1  0  0  0  0
 36 26  2  0  0  0  0
 36 29  1  4  0  0  0
 37 27  1  0  0  0  0
 37 34  2  0  0  0  0
 38 28  1  0  0  0  0
 38 33  2  0  0  0  0
 39 14  1  0  0  0  0
 39 30  1  0  0  0  0
 40 15  1  0  0  0  0
 40 32  1  0  0  0  0
 41 16  1  0  0  0  0
 41 31  1  0  0  0  0
 42 17  1  0  0  0  0
 43 18  1  0  0  0  0
 44 26  1  0  0  0  0
 45 30  2  0  0  0  0
 46 31  2  0  0  0  0
 47 32  2  0  0  0  0
 48 33  1  0  0  0  0
 49 34  1  0  0  0  0
 50 35  2  0  0  0  0
 51 39  1  0  0  0  0
 52 40  1  0  0  0  0
 53 41  1  0  0  0  0
 54 19  1  0  0  0  0
 54 35  1  0  0  0  0
 56 20  1  0  0  0  0
 57 21  1  0  0  0  0
 58 22  1  0  0  0  0
M  CHG  4  51  -1  52  -1  53  -1  55   3
M  END
> <DATABASE_ID>
MMDBc0030162

> <DATABASE_NAME>
MIME

> <SMILES>
[Fe+3].[H]\C(=C(\C)CCO)C(=O)N([O-])CCCC(N=C(C)O)C(=O)OCC\C(C)=C(\[H])C(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(=O)C(\[H])=C(\C)CCO)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H53N6O13.Fe/c1-23(11-17-42)20-30(45)39(51)14-5-8-27-33(48)38-28(34(49)37-27)9-6-15-40(52)32(47)22-25(3)13-19-54-35(50)29(36-26(4)44)10-7-16-41(53)31(46)21-24(2)12-18-43;/h20-22,27-29,42-43H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48);/q-3;+3/b23-20-,24-21+,25-22-;

> <INCHI_KEY>
FQIVLXIUJLOKPL-QYOPVWIVSA-N

> <FORMULA>
C35H53FeN6O13

> <MOLECULAR_WEIGHT>
821.673

> <EXACT_MASS>
821.302002945

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
78.37397577723011

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
iron(3+) ion N-(1-{[(3Z)-4-{[3-(3,6-dihydroxy-5-{3-[(2Z)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]propyl}-2,5-dihydropyrazin-2-yl)propyl](oxido)carbamoyl}-3-methylbut-3-en-1-yl]oxy}-5-[(2E)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]-1-oxopentan-2-yl)ethanimidic acid

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
-0.32025473783469766

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
6.037469237103977

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.290677873070283

> <JCHEM_PKA_STRONGEST_BASIC>
3.6006025330491873

> <JCHEM_POLAR_SURFACE_AREA>
294.64

> <JCHEM_REFRACTIVITY>
194.40120000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iron(3+) ion N-(1-{[(3Z)-4-{[3-(3,6-dihydroxy-5-{3-[(2Z)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]propyl}-2,5-dihydropyrazin-2-yl)propyl](oxido)carbamoyl}-3-methylbut-3-en-1-yl]oxy}-5-[(2E)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]-1-oxopentan-2-yl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 30-MAY-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55 Fe   UNK     0       0.000   0.000   0.000  0.00  0.00          Fe+3
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    8   14                                                       
CONECT    6    9   15                                                       
CONECT    7   10   16                                                       
CONECT    8    5   27                                                       
CONECT    9    6   28                                                       
CONECT   10    7   29                                                       
CONECT   11   17   23                                                       
CONECT   12   18   24                                                       
CONECT   13   19   25                                                       
CONECT   14    5   39                                                       
CONECT   15    6   40                                                       
CONECT   16    7   41                                                       
CONECT   17   11   42                                                       
CONECT   18   12   43                                                       
CONECT   19   13   54                                                       
CONECT   20   23   30   56                                                  
CONECT   21   24   31   57                                                  
CONECT   22   25   32   58                                                  
CONECT   23    1   11   20                                                  
CONECT   24    2   12   21                                                  
CONECT   25    3   13   22                                                  
CONECT   26    4   36   44                                                  
CONECT   27    8   33   37                                                  
CONECT   28    9   34   38                                                  
CONECT   29   10   35   36                                                  
CONECT   30   20   39   45                                                  
CONECT   31   21   41   46                                                  
CONECT   32   22   40   47                                                  
CONECT   33   27   38   48                                                  
CONECT   34   28   37   49                                                  
CONECT   35   29   50   54                                                  
CONECT   36   26   29                                                       
CONECT   37   27   34                                                       
CONECT   38   28   33                                                       
CONECT   39   14   30   51                                                  
CONECT   40   15   32   52                                                  
CONECT   41   16   31   53                                                  
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   26                                                            
CONECT   45   30                                                            
CONECT   46   31                                                            
CONECT   47   32                                                            
CONECT   48   33                                                            
CONECT   49   34                                                            
CONECT   50   35                                                            
CONECT   51   39                                                            
CONECT   52   40                                                            
CONECT   53   41                                                            
CONECT   54   19   35                                                       
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  114    0
END

Synonyms

Value	Source
Iron(3+) ion N-(1-{[(3Z)-4-{[3-(3,6-dihydroxy-5-{3-[(2Z)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]propyl}-2,5-dihydropyrazin-2-yl)propyl](oxido)carbamoyl}-3-methylbut-3-en-1-yl]oxy}-5-[(2E)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]-1-oxopentan-2-yl)ethanimidate	Generator

Chemical Formula

C₃₅H₅₃FeN₆O₁₃

Average Molecular Weight

821.673

Monoisotopic Molecular Weight

821.302002945

IUPAC Name

iron(3+) ion N-(1-{[(3Z)-4-{[3-(3,6-dihydroxy-5-{3-[(2Z)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]propyl}-2,5-dihydropyrazin-2-yl)propyl](oxido)carbamoyl}-3-methylbut-3-en-1-yl]oxy}-5-[(2E)-5-hydroxy-3-methyl-N-oxidopent-2-enamido]-1-oxopentan-2-yl)ethanimidic acid

Traditional Name

CAS Registry Number

31418-71-0

SMILES

[Fe+3].[H]\C(=C(\C)CCO)C(=O)N([O-])CCCC(N=C(C)O)C(=O)OCC\C(C)=C(\[H])C(=O)N([O-])CCCC1N=C(O)C(CCCN([O-])C(=O)C(\[H])=C(\C)CCO)N=C1O

InChI Identifier

InChI=1S/C35H53N6O13.Fe/c1-23(11-17-42)20-30(45)39(51)14-5-8-27-33(48)38-28(34(49)37-27)9-6-15-40(52)32(47)22-25(3)13-19-54-35(50)29(36-26(4)44)10-7-16-41(53)31(46)21-24(2)12-18-43;/h20-22,27-29,42-43H,5-19H2,1-4H3,(H,36,44)(H,37,49)(H,38,48);/q-3;+3/b23-20-,24-21+,25-22-;

InChI Key

FQIVLXIUJLOKPL-QYOPVWIVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Fatty acid ester
1,4-diazinane
Piperazine
Fatty acyl
Acetamide
Carboxamide group
Carboxylic acid ester
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Organic transition metal salt
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic salt
Alcohol
Organooxygen compound
Carbonyl group
Primary alcohol
Organic zwitterion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	2.31	ALOGPS
logP	-0.32	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	5.29	ChemAxon
pKa (Strongest Basic)	3.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	294.64 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	194.4 m³·mol⁻¹	ChemAxon
Polarizability	78.37 Å³	ChemAxon
Number of Rings	1	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1213109710-305c83889be23469ffa1	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-4237029500-df24ac68df840ada3250	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-8294023000-04b77a091e6365fc39df	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-008a-0010001900-593be6585000f38f4166	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001m-2060001900-6ed91bdbd4ad71c97c0b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-8182203900-9af0549e149e617b9556	2019-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

6449889

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 ]
Cui Y, Tu R, Guan Y, Ma L, Chen S: Cloning, sequencing, and characterization of the Azospirillum brasilense fhuE gene. Curr Microbiol. 2006 Mar;52(3):169-77. doi: 10.1007/s00284-005-0008-z. Epub 2006 Feb 18. [PubMed:16502288 ]
Keseler IM, Collado-Vides J, Santos-Zavaleta A, Peralta-Gil M, Gama-Castro S, Muniz-Rascado L, Bonavides-Martinez C, Paley S, Krummenacker M, Altman T, Kaipa P, Spaulding A, Pacheco J, Latendresse M, Fulcher C, Sarker M, Shearer AG, Mackie A, Paulsen I, Gunsalus RP, Karp PD: EcoCyc: a comprehensive database of Escherichia coli biology. Nucleic Acids Res. 2011 Jan;39(Database issue):D583-90. doi: 10.1093/nar/gkq1143. Epub 2010 Nov 21. [PubMed:21097882 ]

Showing metabocard for Ferric coprogen (MMDBc0030162)

MOL for #<Metabolite:0x000055b76e0b16b8>

3D MOL for #<Metabolite:0x000055b76e0b16b8>

3D SDF for #<Metabolite:0x000055b76e0b16b8>

3D-SDF for #<Metabolite:0x000055b76e0b16b8>

PDB for #<Metabolite:0x000055b76e0b16b8>

3D PDB for #<Metabolite:0x000055b76e0b16b8>

SMILES for #<Metabolite:0x000055b76e0b16b8>

INCHI for #<Metabolite:0x000055b76e0b16b8>

Structure for #<Metabolite:0x000055b76e0b16b8>

3D Structure for #<Metabolite:0x000055b76e0b16b8>