MiMeDB: Showing metabocard for Mirubactin (MMDBc0020130)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 10:05:03 UTC

Update Date

2025-10-07 16:07:03 UTC

Metabolite ID

MMDBc0020130

Metabolite Identification

Common Name

Mirubactin

Description

Mirubactin is a siderophore belonging to the chemical class of O-acyl hydroxamic acid esters. Its unique chemical structure features an unprecedented functionality among natural products, which facilitates its role in iron acquisition. Mirubactin is produced by the actinobacterium Actinosynnema mirum, and its biosynthetic gene cluster has been identified, indicating a complex pathway for its synthesis (PMID:22578145 ). The compound has been shown to rescue the lethal effects of cell wall biosynthesis mutations in Bacillus subtilis, suggesting its involvement in bacterial growth and survival under stress conditions (PMID:36312962 ). Notably, mirubactin C, a derivative of mirubactin A, has demonstrated growth-rescuing activity in low micromolar concentrations, although this effect is not solely attributed to iron sequestration, indicating additional biological mechanisms at play (PMID:36312962 ). Furthermore, mirubactin can degrade into multiple siderophores with varying Fe(III) chelation properties, enhancing its functional versatility in iron acquisition (PMID:35703354 ). Overall, mirubactin exemplifies the intricate interplay between microbial metabolites and their ecological roles, particularly in iron homeostasis.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152112052D          

 45 46  0  0  1  0            999 V2000
    1.4289    0.8250    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
    3.5724   -2.0625    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
    2.1434    0.4125    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -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
    2.8579    0.8250    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
    4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    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   -0.4125    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
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    9.2881   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    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
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    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 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 15  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 15  1  0  0  0  0
 27 26  2  0  0  0  0
 28 26  1  0  0  0  0
 29 11  1  0  0  0  0
 29 26  1  0  0  0  0
 16 30  1  6  0  0  0
 30 22  2  0  0  0  0
 17 31  1  6  0  0  0
 31 23  2  0  0  0  0
 32 12  1  0  0  0  0
 32 13  1  0  0  0  0
 33 13  2  0  0  0  0
 34 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 22 38  1  4  0  0  0
 23 39  1  4  0  0  0
 40 24  2  0  0  0  0
 41 24  1  0  0  0  0
 42 25  2  0  0  0  0
 43 25  1  0  0  0  0
 43 32  1  0  0  0  0
 16 44  1  6  0  0  0
 17 45  1  6  0  0  0
M  END


  Mrv1652305152112052D          

 45 46  0  0  1  0            999 V2000
    1.4289    0.8250    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
    3.5724   -2.0625    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
    2.1434    0.4125    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -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
    2.8579    0.8250    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
    4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    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   -0.4125    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
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    9.2881   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    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
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    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 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 15  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 15  1  0  0  0  0
 27 26  2  0  0  0  0
 28 26  1  0  0  0  0
 29 11  1  0  0  0  0
 29 26  1  0  0  0  0
 16 30  1  6  0  0  0
 30 22  2  0  0  0  0
 17 31  1  6  0  0  0
 31 23  2  0  0  0  0
 32 12  1  0  0  0  0
 32 13  1  0  0  0  0
 33 13  2  0  0  0  0
 34 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 22 38  1  4  0  0  0
 23 39  1  4  0  0  0
 40 24  2  0  0  0  0
 41 24  1  0  0  0  0
 42 25  2  0  0  0  0
 43 25  1  0  0  0  0
 43 32  1  0  0  0  0
 16 44  1  6  0  0  0
 17 45  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0020130

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N6O11/c27-26(28)29-11-3-7-16(30-22(38)14-5-1-9-18(34)20(14)36)23(39)31-17(24(40)41)8-4-12-32(13-33)43-25(42)15-6-2-10-19(35)21(15)37/h1-2,5-6,9-10,13,16-17,34-37H,3-4,7-8,11-12H2,(H,30,38)(H,31,39)(H,40,41)(H4,27,28,29)/t16-,17-/m1/s1

> <INCHI_KEY>
JANBVBCLMZUUHR-IAGOWNOFSA-N

> <FORMULA>
C26H32N6O11

> <MOLECULAR_WEIGHT>
604.573

> <EXACT_MASS>
604.212905874

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.78283602024308

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2R)-5-carbamimidamido-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxypentylidene]amino}-5-[N-(2,3-dihydroxybenzoyloxy)formamido]pentanoic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.9078598885344716

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.593697638040818

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6913504102207924

> <JCHEM_PKA_STRONGEST_BASIC>
11.801550051733

> <JCHEM_POLAR_SURFACE_AREA>
291.90999999999997

> <JCHEM_REFRACTIVITY>
159.55290000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2R)-5-carbamimidamido-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxypentylidene]amino}-5-[N-(2,3-dihydroxybenzoyloxy)formamido]pentanoic 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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.006  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.673  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.668  -8.470   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       4.001  -8.470   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       5.335  -6.160   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      10.669  -1.540   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      17.338  -0.770   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      18.672   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      22.673  -5.390   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      20.005   0.770   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
HETATM   44  H   UNK     0       9.336  -2.310   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      13.337   0.000   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   32                                                       
CONECT   13   32   33                                                       
CONECT   14    5   20   22                                                  
CONECT   15    6   21   25                                                  
CONECT   16    7   23   30   44                                             
CONECT   17    8   24   31   45                                             
CONECT   18    9   20   34                                                  
CONECT   19   10   21   35                                                  
CONECT   20   14   18   36                                                  
CONECT   21   15   19   37                                                  
CONECT   22   14   30   38                                                  
CONECT   23   16   31   39                                                  
CONECT   24   17   40   41                                                  
CONECT   25   15   42   43                                                  
CONECT   26   27   28   29                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   11   26                                                       
CONECT   30   16   22                                                       
CONECT   31   17   23                                                       
CONECT   32   12   13   43                                                  
CONECT   33   13                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   24                                                            
CONECT   42   25                                                            
CONECT   43   25   32                                                       
CONECT   44   16                                                            
CONECT   45   17                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   92    0
END

Synonyms

Not Available

Molecular Formula

C₂₆H₃₂N₆O₁₁

Average Mass

604.573

Monoisotopic Mass

604.212905874

IUPAC Name

(2R)-2-{[(2R)-5-carbamimidamido-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxypentylidene]amino}-5-[N-(2,3-dihydroxybenzoyloxy)formamido]pentanoic acid

Traditional Name

(2R)-2-{[(2R)-5-carbamimidamido-2-{[(2,3-dihydroxyphenyl)(hydroxy)methylidene]amino}-1-hydroxypentylidene]amino}-5-[N-(2,3-dihydroxybenzoyloxy)formamido]pentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H32N6O11/c27-26(28)29-11-3-7-16(30-22(38)14-5-1-9-18(34)20(14)36)23(39)31-17(24(40)41)8-4-12-32(13-33)43-25(42)15-6-2-10-19(35)21(15)37/h1-2,5-6,9-10,13,16-17,34-37H,3-4,7-8,11-12H2,(H,30,38)(H,31,39)(H,40,41)(H4,27,28,29)/t16-,17-/m1/s1

InChI Key

JANBVBCLMZUUHR-IAGOWNOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Hippuric acid or derivatives
N-acyl-alpha-amino acid
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
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Benzenoid
Vinylogous acid
Carboxylic acid salt
Carboxamide group
Guanidine
Secondary carboxylic acid amide
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	0.99	ALOGPS
logP	0.91	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	11.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	291.91 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	159.55 m³·mol⁻¹	ChemAxon
Polarizability	57.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

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	Actinobacteria	2	Human ; Human urine	Metabolic reconstruction; Microbial culture
Bacteria	Actinobacteria	20	Human ; Human urine	Metabolic reconstruction; Microbial culture

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

78440503

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mirubactin

METLIN ID

Not Available

PubChem Compound

59051490

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

JANBVBCLMZUUHR-UHFFFAOYSA-N

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 Mirubactin (MMDBc0020130)

MOL for #<Metabolite:0x00007f8dc88e11a8>

3D MOL for #<Metabolite:0x00007f8dc88e11a8>

3D SDF for #<Metabolite:0x00007f8dc88e11a8>

3D-SDF for #<Metabolite:0x00007f8dc88e11a8>

PDB for #<Metabolite:0x00007f8dc88e11a8>

3D PDB for #<Metabolite:0x00007f8dc88e11a8>

SMILES for #<Metabolite:0x00007f8dc88e11a8>

INCHI for #<Metabolite:0x00007f8dc88e11a8>

Structure for #<Metabolite:0x00007f8dc88e11a8>

3D Structure for #<Metabolite:0x00007f8dc88e11a8>