MiMeDB: Showing metabocard for Heterobactin A (MMDBc0004201)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:17:37 UTC

Update Date

2025-10-07 16:04:50 UTC

Metabolite ID

MMDBc0004201

Metabolite Identification

Common Name

Heterobactin A

Description

Heterobactin A is a siderophore, a class of metabolites that play a crucial role in iron chelation and transport in microbial systems. This compound, characterized by its unique structure, features a peptide bond linking the guanidine group of an arginine residue to a 2,3-dihydroxybenzoate moiety, as elucidated through MS(n) analysis and NMR spectroscopy (PMID:24274668 ). Heterobactin A is known to form 1:1 ligand/metal complexes, which is critical for its function in iron acquisition (PMID:22539866 ). Variants of heterobactin A, such as heterobactin S1 and S2, exhibit sulfonation modifications on the aromatic rings, indicating the potential for structural diversity within this chemical class (PMID:24274668 ). Notably, heterobactin A is selectively recognized by the catecholate receptor Cir in E. coli, contrasting with heterobactin B, which is taken up by both E. coli and A. (PMID:11508844 ). The presence of heterobactin A alongside heterobactin B in various biological samples underscores its significance in microbial ecology and iron metabolism (PMID:33511442 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100172D          

 46 48  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  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  8  1  0  0  0  0
 18  9  2  0  0  0  0
 19 10  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 28 27  2  0  0  0  0
 29 11  1  0  0  0  0
 29 27  1  0  0  0  0
 30 13  1  4  0  0  0
 30 25  2  0  0  0  0
 17 31  1  1  0  0  0
 31 20  2  0  0  0  0
 16 32  1  1  0  0  0
 32 23  2  0  0  0  0
 33 24  2  0  0  0  0
 33 27  1  4  0  0  0
 34 12  1  0  0  0  0
 34 26  1  0  0  0  0
 35 18  1  0  0  0  0
 36 19  1  0  0  0  0
 20 37  1  4  0  0  0
 38 21  1  0  0  0  0
 39 22  1  0  0  0  0
 23 40  1  4  0  0  0
 41 24  1  0  0  0  0
 42 25  1  0  0  0  0
 43 26  2  0  0  0  0
 44 34  1  0  0  0  0
 16 45  1  1  0  0  0
 17 46  1  6  0  0  0
M  END


  Mrv1652305152100172D          

 46 48  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  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  8  1  0  0  0  0
 18  9  2  0  0  0  0
 19 10  2  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 21 18  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 28 27  2  0  0  0  0
 29 11  1  0  0  0  0
 29 27  1  0  0  0  0
 30 13  1  4  0  0  0
 30 25  2  0  0  0  0
 17 31  1  1  0  0  0
 31 20  2  0  0  0  0
 16 32  1  1  0  0  0
 32 23  2  0  0  0  0
 33 24  2  0  0  0  0
 33 27  1  4  0  0  0
 34 12  1  0  0  0  0
 34 26  1  0  0  0  0
 35 18  1  0  0  0  0
 36 19  1  0  0  0  0
 20 37  1  4  0  0  0
 38 21  1  0  0  0  0
 39 22  1  0  0  0  0
 23 40  1  4  0  0  0
 41 24  1  0  0  0  0
 42 25  1  0  0  0  0
 43 26  2  0  0  0  0
 44 34  1  0  0  0  0
 16 45  1  1  0  0  0
 17 46  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004201

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](CCCNC(=N)N=C(O)C1=C(O)C(O)=CC=C1)(N=C(O)C1=C(O)C(O)=CC=C1)C(O)=NCC(O)=N[C@@]1([H])CCCN(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N7O10/c28-27(33-24(41)15-6-2-10-19(36)22(15)39)29-11-3-7-16(32-23(40)14-5-1-9-18(35)21(14)38)25(42)30-13-20(37)31-17-8-4-12-34(44)26(17)43/h1-2,5-6,9-10,16-17,35-36,38-39,44H,3-4,7-8,11-13H2,(H,30,42)(H,31,37)(H,32,40)(H3,28,29,33,41)/t16-,17+/m1/s1

> <INCHI_KEY>
SDUJQEWEVFATFH-SJORKVTESA-N

> <FORMULA>
C27H33N7O10

> <MOLECULAR_WEIGHT>
615.6

> <EXACT_MASS>
615.228890291

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.33896787327437

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-5-[({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}methanimidoyl)amino]-N-({[(3S)-1-hydroxy-2-oxopiperidin-3-yl]-C-hydroxycarbonimidoyl}methyl)pentanimidic acid

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.0211565682128516

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.3244174296160174

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4457817642767514

> <JCHEM_PKA_STRONGEST_BASIC>
15.000003614654057

> <JCHEM_POLAR_SURFACE_AREA>
287.7

> <JCHEM_REFRACTIVITY>
165.53890000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-5-[({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}methanimidoyl)amino]-N-({[(3S)-1-hydroxy-2-oxopiperidin-3-yl]-C-hydroxycarbonimidoyl}methyl)pentanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.006   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.339   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.006   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      17.338  -2.310   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      16.004   0.000   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      10.669   1.540   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      18.672   0.000   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      25.340  -0.770   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      22.673  -2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      20.005  -2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      10.669  -1.540   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1    5    9                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   12                                                       
CONECT    5    1   14                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    4   17                                                       
CONECT    9    1   18                                                       
CONECT   10    2   19                                                       
CONECT   11    3   29                                                       
CONECT   12    4   34                                                       
CONECT   13   20   30                                                       
CONECT   14    5   21   23                                                  
CONECT   15    6   22   24                                                  
CONECT   16    7   25   32   45                                             
CONECT   17    8   26   31   46                                             
CONECT   18    9   21   35                                                  
CONECT   19   10   22   36                                                  
CONECT   20   13   31   37                                                  
CONECT   21   14   18   38                                                  
CONECT   22   15   19   39                                                  
CONECT   23   14   32   40                                                  
CONECT   24   15   33   41                                                  
CONECT   25   16   30   42                                                  
CONECT   26   17   34   43                                                  
CONECT   27   28   29   33                                                  
CONECT   28   27                                                            
CONECT   29   11   27                                                       
CONECT   30   13   25                                                       
CONECT   31   17   20                                                       
CONECT   32   16   23                                                       
CONECT   33   24   27                                                       
CONECT   34   12   26   44                                                  
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
CONECT   40   23                                                            
CONECT   41   24                                                            
CONECT   42   25                                                            
CONECT   43   26                                                            
CONECT   44   34                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

Synonyms

Value	Source
(2R)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-5-[({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}methanimidoyl)amino]-N-({[(3S)-1-hydroxy-2-oxopiperidin-3-yl]-C-hydroxycarbonimidoyl}methyl)pentanimidate	Generator

Molecular Formula

C₂₇H₃₃N₇O₁₀

Average Mass

615.6

Monoisotopic Mass

615.228890291

IUPAC Name

(2R)-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-5-[({[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}methanimidoyl)amino]-N-({[(3S)-1-hydroxy-2-oxopiperidin-3-yl]-C-hydroxycarbonimidoyl}methyl)pentanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@](CCCNC(=N)N=C(O)C1=C(O)C(O)=CC=C1)(N=C(O)C1=C(O)C(O)=CC=C1)C(O)=NCC(O)=N[C@@]1([H])CCCN(O)C1=O

InChI Identifier

InChI=1S/C27H33N7O10/c28-27(33-24(41)15-6-2-10-19(36)22(15)39)29-11-3-7-16(32-23(40)14-5-1-9-18(35)21(14)38)25(42)30-13-20(37)31-17-8-4-12-34(44)26(17)43/h1-2,5-6,9-10,16-17,35-36,38-39,44H,3-4,7-8,11-13H2,(H,30,42)(H,31,37)(H,32,40)(H3,28,29,33,41)/t16-,17+/m1/s1

InChI Key

SDUJQEWEVFATFH-SJORKVTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Arginine or derivatives
Hippuric acid or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Salicylamide
Salicylic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Catechol
Acylguanidine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Delta-lactam
Phenol
Piperidinone
Benzenoid
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Fatty acyl
Piperidine
Vinylogous acid
Secondary carboxylic acid amide
Lactam
Hydroxamic acid
Carboxamide group
Guanidine
Organoheterocyclic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organic 1,3-dipolar compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen 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
Water Solubility	0.08 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.02	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.45	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	287.7 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	165.54 m³·mol⁻¹	ChemAxon
Polarizability	60.34 Å³	ChemAxon
Number of Rings	3	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

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species

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	Actinobacteria	1	Human	Metabolic reconstruction

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

30900652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584061

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Heterobactin A (MMDBc0004201)

MOL for #<Metabolite:0x00007f2ad6c1c430>

3D MOL for #<Metabolite:0x00007f2ad6c1c430>

3D SDF for #<Metabolite:0x00007f2ad6c1c430>

3D-SDF for #<Metabolite:0x00007f2ad6c1c430>

PDB for #<Metabolite:0x00007f2ad6c1c430>

3D PDB for #<Metabolite:0x00007f2ad6c1c430>

SMILES for #<Metabolite:0x00007f2ad6c1c430>

INCHI for #<Metabolite:0x00007f2ad6c1c430>

Structure for #<Metabolite:0x00007f2ad6c1c430>

3D Structure for #<Metabolite:0x00007f2ad6c1c430>