MiMeDB: Showing metabocard for Fusaricidin B (MMDBc0001379)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 19:36:37 UTC

Update Date

2025-10-07 16:04:28 UTC

Metabolite ID

MMDBc0001379

Metabolite Identification

Common Name

Fusaricidin B

Description

Fusaricidin B is a lipopeptide antibiotic belonging to the chemical class of cyclic depsipeptides. It is produced by the bacterium Paenibacillus polymyxa and has garnered attention for its antimicrobial properties, particularly against various pathogenic fungi and its potential anti-tubercular applications. The biosynthetic gene clusters responsible for the production of fusaricidin B have been identified through genomic analysis, revealing its association with other antimicrobial compounds such as polymyxin and tridecaptin (PMID:40057921 ). Additionally, studies utilizing antiSMASH predicted multiple secondary metabolic biosynthetic gene clusters, including those for fusaricidin B and related antifungal peptides (PMID:38481158 ). The compound has been characterized through alkaline hydrolysis and sequence analysis, confirming its structure as a cyclic depsipeptide (PMID:28295433 ). Notably, the highest production concentrations of fusaricidin B reported in the literature reached 118 mg L-1 (PMID:28295433 ). Furthermore, research has demonstrated that fusaricidin B plays a significant role in the defense mechanisms of certain biocontrol agents (PMID:23636858 ) and has been identified as a principal component in various biological assays (PMID:23113815 ). The elucidation of its structure has been achieved through NMR experiments and amino acid analysis (PMID:9439693 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142121362D          

 72 72  0  0  1  0            999 V2000
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3907   -8.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387  -11.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4403   -9.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4582   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8756   -9.0430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460  -11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1815   -8.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9555   -9.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6207   -9.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8868   -9.1218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -10.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -9.0430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -13.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -12.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1994   -7.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598  -10.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3033  -10.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7671  -10.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0849  -10.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0608   -9.1720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -11.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4270  -10.7327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -14.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -12.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987  -11.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 25  5  1  1  0  0  0
 26  6  1  0  0  0  0
 27  7  1  0  0  0  0
 28 18  1  0  0  0  0
 28 22  1  0  0  0  0
 29 19  1  1  0  0  0
 30 20  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  1  0  0  0
 33 24  1  6  0  0  0
 34 26  1  6  0  0  0
 35 27  1  0  0  0  0
 36 29  1  0  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 39 34  1  0  0  0  0
 40 35  1  0  0  0  0
 41 25  1  0  0  0  0
 43 30  2  0  0  0  0
 44 42  2  0  0  0  0
 45 42  1  0  0  0  0
 46 21  1  0  0  0  0
 46 42  1  0  0  0  0
 47 25  1  0  0  0  0
 47 36  2  0  0  0  0
 48 29  1  0  0  0  0
 48 39  2  0  0  0  0
 49 31  2  0  0  0  0
 35 49  1  6  0  0  0
 50 33  1  0  0  0  0
 50 37  2  0  0  0  0
 51 32  1  0  0  0  0
 51 40  2  0  0  0  0
 52 34  1  0  0  0  0
 52 38  2  0  0  0  0
 26 53  1  6  0  0  0
 54 28  1  0  0  0  0
 55 30  1  0  0  0  0
 31 56  1  4  0  0  0
 36 57  1  4  0  0  0
 37 58  1  4  0  0  0
 38 59  1  4  0  0  0
 39 60  1  4  0  0  0
 40 61  1  4  0  0  0
 62 41  2  0  0  0  0
 63 27  1  0  0  0  0
 63 41  1  0  0  0  0
 25 64  1  6  0  0  0
 26 65  1  1  0  0  0
 66 27  1  0  0  0  0
 67 28  1  0  0  0  0
 29 68  1  6  0  0  0
 32 69  1  6  0  0  0
 33 70  1  1  0  0  0
 34 71  1  6  0  0  0
 35 72  1  6  0  0  0
M  END


  Mrv1652305142121362D          

 72 72  0  0  1  0            999 V2000
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3907   -8.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387  -11.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4403   -9.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4582   -9.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8756   -9.0430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1460  -11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1815   -8.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4315  -12.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9555   -9.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6207   -9.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8868   -9.1218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -10.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -9.0430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -11.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -13.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -12.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1994   -7.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598  -10.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3033  -10.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7671  -10.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0849  -10.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0608   -9.1720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -11.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -10.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4270  -10.7327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -13.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -14.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -12.7875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987  -11.5500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 25  5  1  1  0  0  0
 26  6  1  0  0  0  0
 27  7  1  0  0  0  0
 28 18  1  0  0  0  0
 28 22  1  0  0  0  0
 29 19  1  1  0  0  0
 30 20  1  0  0  0  0
 31 22  1  0  0  0  0
 32 23  1  1  0  0  0
 33 24  1  6  0  0  0
 34 26  1  6  0  0  0
 35 27  1  0  0  0  0
 36 29  1  0  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 39 34  1  0  0  0  0
 40 35  1  0  0  0  0
 41 25  1  0  0  0  0
 43 30  2  0  0  0  0
 44 42  2  0  0  0  0
 45 42  1  0  0  0  0
 46 21  1  0  0  0  0
 46 42  1  0  0  0  0
 47 25  1  0  0  0  0
 47 36  2  0  0  0  0
 48 29  1  0  0  0  0
 48 39  2  0  0  0  0
 49 31  2  0  0  0  0
 35 49  1  6  0  0  0
 50 33  1  0  0  0  0
 50 37  2  0  0  0  0
 51 32  1  0  0  0  0
 51 40  2  0  0  0  0
 52 34  1  0  0  0  0
 52 38  2  0  0  0  0
 26 53  1  6  0  0  0
 54 28  1  0  0  0  0
 55 30  1  0  0  0  0
 31 56  1  4  0  0  0
 36 57  1  4  0  0  0
 37 58  1  4  0  0  0
 38 59  1  4  0  0  0
 39 60  1  4  0  0  0
 40 61  1  4  0  0  0
 62 41  2  0  0  0  0
 63 27  1  0  0  0  0
 63 41  1  0  0  0  0
 25 64  1  6  0  0  0
 26 65  1  1  0  0  0
 66 27  1  0  0  0  0
 67 28  1  0  0  0  0
 29 68  1  6  0  0  0
 32 69  1  6  0  0  0
 33 70  1  1  0  0  0
 34 71  1  6  0  0  0
 35 72  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001379

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(CCCCCCCCCCCCNC(N)=N)CC(O)=N[C@]1([H])C(O)=N[C@]([H])(C(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(C(O)=N[C@]([H])(CCC(O)=N)C(O)=N[C@]([H])(C)C(=O)OC1([H])C)[C@]([H])(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C42H76N10O11/c1-23(2)32-37(58)50-33(24(3)4)38(59)52-34(26(6)53)39(60)48-29(19-20-30(43)55)36(57)47-25(5)41(62)63-27(7)35(40(61)51-32)49-31(56)22-28(54)18-16-14-12-10-8-9-11-13-15-17-21-46-42(44)45/h23-29,32-35,53-54H,8-22H2,1-7H3,(H2,43,55)(H,47,57)(H,48,60)(H,49,56)(H,50,58)(H,51,61)(H,52,59)(H4,44,45,46)/t25-,26+,27?,28?,29-,32-,33+,34-,35+/m1/s1

> <INCHI_KEY>
WDNFMLNXGKOBJN-QWDDQTKWSA-N

> <FORMULA>
C42H76N10O11

> <MOLECULAR_WEIGHT>
897.129

> <EXACT_MASS>
896.569503307

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
97.9622624979506

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-carbamimidamido-3-hydroxy-N-[(3R,6R,9R,12S,15R,18S)-5,8,11,14,17-pentahydroxy-6-[2-(C-hydroxycarbonimidoyl)ethyl]-9-[(1S)-1-hydroxyethyl]-3,19-dimethyl-2-oxo-12,15-bis(propan-2-yl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]pentadecanimidic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
3.271802409459784

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.213055227865357

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.722353367066255

> <JCHEM_PKA_STRONGEST_BASIC>
12.26524150366537

> <JCHEM_POLAR_SURFACE_AREA>
368.2800000000001

> <JCHEM_REFRACTIVITY>
255.18670000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-carbamimidamido-3-hydroxy-N-[(3R,6R,9R,12S,15R,18S)-5,8,11,14,17-pentahydroxy-6-[2-(C-hydroxycarbonimidoyl)ethyl]-9-[(1S)-1-hydroxyethyl]-12,15-diisopropyl-3,19-dimethyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]pentadecanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.005 -28.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.673 -28.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.663 -15.634   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.673 -20.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.139 -20.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -22.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -22.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -22.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -22.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -22.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336 -22.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.355 -18.509   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.389 -16.970   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003 -22.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.339 -27.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.568 -16.880   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.673 -22.330   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.739 -16.229   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.339 -26.180   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.339 -23.100   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.584 -18.345   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.673 -25.410   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.339 -21.560   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.092 -18.345   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      24.055 -17.027   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      -9.336 -22.330   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      -8.002 -20.020   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      -6.668 -22.330   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      18.108 -16.880   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      20.005 -20.790   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0      14.670 -22.330   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0      20.005 -25.410   0.000  0.00  0.00           N+0
HETATM   51  N   UNK     0      17.338 -23.870   0.000  0.00  0.00           N+0
HETATM   52  N   UNK     0      22.673 -23.870   0.000  0.00  0.00           N+0
HETATM   53  O   UNK     0      24.006 -23.100   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      10.669 -20.020   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      22.772 -14.689   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      12.432 -20.314   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      17.366 -19.288   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      18.672 -27.720   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      24.006 -26.180   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      21.965 -20.153   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      14.670 -23.870   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      16.959 -19.618   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      14.670 -19.250   0.000  0.00  0.00           O+0
HETATM   64  H   UNK     0      15.047 -17.121   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      24.006 -21.560   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      16.004 -20.020   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      10.669 -23.100   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      21.330 -20.034   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      16.004 -24.640   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      20.005 -26.950   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      20.005 -23.870   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      17.544 -21.560   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6   26                                                            
CONECT    7   27                                                            
CONECT    8    9   10                                                       
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   21                                                       
CONECT   18   16   28                                                       
CONECT   19   20   29                                                       
CONECT   20   19   30                                                       
CONECT   21   17   46                                                       
CONECT   22   28   31                                                       
CONECT   23    1    2   32                                                  
CONECT   24    3    4   33                                                  
CONECT   25    5   41   47   64                                             
CONECT   26    6   34   53   65                                             
CONECT   27    7   35   63   66                                             
CONECT   28   18   22   54   67                                             
CONECT   29   19   36   48   68                                             
CONECT   30   20   43   55                                                  
CONECT   31   22   49   56                                                  
CONECT   32   23   37   51   69                                             
CONECT   33   24   38   50   70                                             
CONECT   34   26   39   52   71                                             
CONECT   35   27   40   49   72                                             
CONECT   36   29   47   57                                                  
CONECT   37   32   50   58                                                  
CONECT   38   33   52   59                                                  
CONECT   39   34   48   60                                                  
CONECT   40   35   51   61                                                  
CONECT   41   25   62   63                                                  
CONECT   42   44   45   46                                                  
CONECT   43   30                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
CONECT   46   21   42                                                       
CONECT   47   25   36                                                       
CONECT   48   29   39                                                       
CONECT   49   31   35                                                       
CONECT   50   33   37                                                       
CONECT   51   32   40                                                       
CONECT   52   34   38                                                       
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   36                                                            
CONECT   58   37                                                            
CONECT   59   38                                                            
CONECT   60   39                                                            
CONECT   61   40                                                            
CONECT   62   41                                                            
CONECT   63   27   41                                                       
CONECT   64   25                                                            
CONECT   65   26                                                            
CONECT   66   27                                                            
CONECT   67   28                                                            
CONECT   68   29                                                            
CONECT   69   32                                                            
CONECT   70   33                                                            
CONECT   71   34                                                            
CONECT   72   35                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  144    0
END

Synonyms

Not Available

Molecular Formula

C₄₂H₇₆N₁₀O₁₁

Average Mass

897.129

Monoisotopic Mass

896.569503307

IUPAC Name

15-carbamimidamido-3-hydroxy-N-[(3R,6R,9R,12S,15R,18S)-5,8,11,14,17-pentahydroxy-6-[2-(C-hydroxycarbonimidoyl)ethyl]-9-[(1S)-1-hydroxyethyl]-3,19-dimethyl-2-oxo-12,15-bis(propan-2-yl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]pentadecanimidic acid

Traditional Name

15-carbamimidamido-3-hydroxy-N-[(3R,6R,9R,12S,15R,18S)-5,8,11,14,17-pentahydroxy-6-[2-(C-hydroxycarbonimidoyl)ethyl]-9-[(1S)-1-hydroxyethyl]-12,15-diisopropyl-3,19-dimethyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]pentadecanimidic acid

CAS Registry Number

Not Available

SMILES

[H]C(O)(CCCCCCCCCCCCNC(N)=N)CC(O)=N[C@]1([H])C(O)=N[C@]([H])(C(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(C(O)=N[C@]([H])(CCC(O)=N)C(O)=N[C@]([H])(C)C(=O)OC1([H])C)[C@]([H])(C)O

InChI Identifier

InChI=1S/C42H76N10O11/c1-23(2)32-37(58)50-33(24(3)4)38(59)52-34(26(6)53)39(60)48-29(19-20-30(43)55)36(57)47-25(5)41(62)63-27(7)35(40(61)51-32)49-31(56)22-28(54)18-16-14-12-10-8-9-11-13-15-17-21-46-42(44)45/h23-29,32-35,53-54H,8-22H2,1-7H3,(H2,43,55)(H,47,57)(H,48,60)(H,49,56)(H,50,58)(H,51,61)(H,52,59)(H4,44,45,46)/t25-,26+,27?,28?,29-,32-,33+,34-,35+/m1/s1

InChI Key

WDNFMLNXGKOBJN-QWDDQTKWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Cyclic carboximidic acid
Secondary alcohol
Lactone
Guanidine
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Alcohol
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	0.033 g/L	ALOGPS
logP	2.39	ALOGPS
logP	3.27	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	12.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	368.28 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	255.19 m³·mol⁻¹	ChemAxon
Polarizability	97.96 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

Not Available

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	639.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	307.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	611.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	494.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	453.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	129.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1727.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	628.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	180.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	202.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	248.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	163.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	163.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	31.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	242.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	166.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	421.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	963.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	965.3

Retention Indices

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	Firmicutes	1		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

C00016311

Chemspider ID

78436306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583239

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Fusaricidin B (MMDBc0001379)

MOL for #<Metabolite:0x00007f9ac4684550>

3D MOL for #<Metabolite:0x00007f9ac4684550>

3D SDF for #<Metabolite:0x00007f9ac4684550>

3D-SDF for #<Metabolite:0x00007f9ac4684550>

PDB for #<Metabolite:0x00007f9ac4684550>

3D PDB for #<Metabolite:0x00007f9ac4684550>

SMILES for #<Metabolite:0x00007f9ac4684550>

INCHI for #<Metabolite:0x00007f9ac4684550>

Structure for #<Metabolite:0x00007f9ac4684550>

3D Structure for #<Metabolite:0x00007f9ac4684550>