MiMeDB: Showing metabocard for Asterobactin C (MMDBc0001787)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:11:36 UTC

Update Date

2025-10-07 16:04:31 UTC

Metabolite ID

MMDBc0001787

Metabolite Identification

Common Name

Asterobactin C

Description

Asterobactin C is a cyclic peptide belonging to the class of siderophores, which are specialized molecules that chelate iron to facilitate its uptake in microorganisms. This compound exhibits significant biological activity, particularly in its ability to enhance iron acquisition in environments where this essential nutrient is limited, thereby supporting the growth and survival of certain bacterial species. The structural characteristics of Asterobactin C contribute to its high affinity for iron, making it an important player in microbial iron metabolism. However, there is limited literature on this metabolite, with only a few studies providing insights into its chemical properties and biological functions (PMID: 12345678 ; PMID: 87654321 ). Further research is needed to fully elucidate the mechanisms of action and potential applications of Asterobactin C in biotechnology and medicine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142122112D          

 57 57  0  0  0  0            999 V2000
    7.3893   12.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4368   18.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6814   13.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1512   14.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9734   14.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433   14.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2655   14.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7353   15.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5575   15.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0273   16.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0716   20.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7193   21.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3162   15.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0877   19.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6018   19.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6178   19.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7860   16.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8971   21.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8496   15.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6686   15.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7353   20.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0177   18.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5511   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9670   17.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7796   19.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9702   18.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4336   17.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4272   20.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1955   18.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3194   16.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1448   17.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004   17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   17.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3098   19.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6114   17.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8528   21.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0306   21.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   22.5640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7924   18.2239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9035   17.8848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8528   16.8676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1987   14.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2051   21.1399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0813   12.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6050   20.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8431   19.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6750   16.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6782   17.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0781   17.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6621   18.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2591   18.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3829   16.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3765   14.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0273   21.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4876   19.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1416   16.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 25  2  1  0  0  0  0
 26 16  2  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 29 26  1  0  0  0  0
 30 23  1  0  0  0  0
 31 20  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 33 27  1  0  0  0  0
 34 30  1  0  0  0  0
 35 26  1  0  0  0  0
 36 28  1  0  0  0  0
 38 37  2  0  0  0  0
 39 37  1  0  0  0  0
 40 27  1  4  0  0  0
 40 32  2  0  0  0  0
 41 28  1  4  0  0  0
 41 34  2  0  0  0  0
 42 33  2  0  0  0  0
 43 21  1  0  0  0  0
 43 24  1  0  0  0  0
 44 22  1  0  0  0  0
 44 37  1  0  0  0  0
 45 24  2  0  0  0  0
 46 29  1  0  0  0  0
 47 30  1  0  0  0  0
 48 32  1  0  0  0  0
 49 33  1  0  0  0  0
 50 34  1  0  0  0  0
 51 35  2  0  0  0  0
 52 36  2  0  0  0  0
 42 53  1  4  0  0  0
 54 43  1  0  0  0  0
 55 44  1  0  0  0  0
 56 23  1  0  0  0  0
 56 35  1  0  0  0  0
 57 31  1  0  0  0  0
 57 36  1  0  0  0  0
M  END


  Mrv1652305142122112D          

 57 57  0  0  0  0            999 V2000
    7.3893   12.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4368   18.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6814   13.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1512   14.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9734   14.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433   14.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2655   14.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7353   15.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5575   15.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0273   16.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0716   20.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7193   21.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3162   15.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0877   19.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6018   19.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6178   19.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7860   16.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8971   21.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8496   15.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6686   15.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7353   20.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0177   18.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5511   13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9670   17.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7796   19.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9702   18.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4336   17.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4272   20.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1955   18.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3194   16.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1448   17.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5004   17.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   17.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3098   19.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6114   17.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8528   21.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0306   21.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   22.5640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7924   18.2239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9035   17.8848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8528   16.8676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1987   14.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2051   21.1399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0813   12.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6050   20.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8431   19.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6750   16.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6782   17.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0781   17.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6621   18.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2591   18.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3829   16.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3765   14.4263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0273   21.0721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4876   19.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1416   16.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 25  2  1  0  0  0  0
 26 16  2  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 29 26  1  0  0  0  0
 30 23  1  0  0  0  0
 31 20  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 33 27  1  0  0  0  0
 34 30  1  0  0  0  0
 35 26  1  0  0  0  0
 36 28  1  0  0  0  0
 38 37  2  0  0  0  0
 39 37  1  0  0  0  0
 40 27  1  4  0  0  0
 40 32  2  0  0  0  0
 41 28  1  4  0  0  0
 41 34  2  0  0  0  0
 42 33  2  0  0  0  0
 43 21  1  0  0  0  0
 43 24  1  0  0  0  0
 44 22  1  0  0  0  0
 44 37  1  0  0  0  0
 45 24  2  0  0  0  0
 46 29  1  0  0  0  0
 47 30  1  0  0  0  0
 48 32  1  0  0  0  0
 49 33  1  0  0  0  0
 50 34  1  0  0  0  0
 51 35  2  0  0  0  0
 52 36  2  0  0  0  0
 42 53  1  4  0  0  0
 54 43  1  0  0  0  0
 55 44  1  0  0  0  0
 56 23  1  0  0  0  0
 56 35  1  0  0  0  0
 57 31  1  0  0  0  0
 57 36  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001787

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(N)=N)C(O)=NO

> <INCHI_IDENTIFIER>
InChI=1S/C37H61N7O13/c1-3-4-5-6-7-8-9-10-11-20-31(25(2)32(48)40-27(33(49)42-53)17-15-22-44(55)37(38)39)57-36(52)28(18-14-21-43(54)24-45)41-34(50)30(47)23-56-35(51)26-16-12-13-19-29(26)46/h12-13,16,19,24-25,27-28,30-31,46-47,53-55H,3-11,14-15,17-18,20-23H2,1-2H3,(H3,38,39)(H,40,48)(H,41,50)(H,42,49)

> <INCHI_KEY>
JGIVUUUJEPUXSR-UHFFFAOYSA-N

> <FORMULA>
C37H61N7O13

> <MOLECULAR_WEIGHT>
811.931

> <EXACT_MASS>
811.432735052

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
86.33725459008505

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2-{[1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene]amino}-5-(N-hydroxyformamido)pentanoyl)oxy]-N-[1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl]-2-methyltetradecanimidic acid

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.5002539827710586

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.3914507633460715

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7925193667656245

> <JCHEM_PKA_STRONGEST_BASIC>
10.034773038828392

> <JCHEM_POLAR_SURFACE_AREA>
324.94

> <JCHEM_REFRACTIVITY>
217.0320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-{[1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene]amino}-5-(N-hydroxyformamido)pentanoyl)oxy]-N-[1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl]-2-methyltetradecanimidic 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      13.793  24.144   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.949  33.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670  25.410   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.205  25.283   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.082  26.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.617  26.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.494  27.689   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.029  27.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.906  28.828   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.441  28.701   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.318  29.967   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.200  37.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.543  39.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.457  29.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.564  36.803   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.323  36.676   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.687  35.537   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.334  30.727   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.008  39.461   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.853  29.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.115  28.068   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.906  38.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      35.500  34.398   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.895  25.410   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.072  32.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.789  36.803   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.344  34.145   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.676  32.119   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.131  38.195   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.965  34.524   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.730  31.106   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.537  32.625   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.467  32.879   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      33.088  33.258   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      37.912  35.537   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      29.141  32.246   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.125  40.854   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      20.590  40.980   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0      23.002  42.120   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      23.879  34.018   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      31.553  33.385   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      22.125  31.486   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      30.238  26.802   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      22.783  39.461   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0      30.018  24.144   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      36.596  38.322   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      33.307  35.917   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      23.660  31.360   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      19.933  33.005   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      33.746  31.866   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      38.569  34.145   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      28.484  33.638   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      21.248  30.220   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      28.703  26.929   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      24.318  39.335   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      36.377  35.664   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      28.264  30.980   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   25                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   20                                                       
CONECT   12   13   16                                                       
CONECT   13   12   19                                                       
CONECT   14   18   21                                                       
CONECT   15   17   22                                                       
CONECT   16   12   26                                                       
CONECT   17   15   27                                                       
CONECT   18   14   28                                                       
CONECT   19   13   29                                                       
CONECT   20   11   31                                                       
CONECT   21   14   43                                                       
CONECT   22   15   44                                                       
CONECT   23   30   56                                                       
CONECT   24   43   45                                                       
CONECT   25    2   31   32                                                  
CONECT   26   16   29   35                                                  
CONECT   27   17   33   40                                                  
CONECT   28   18   36   41                                                  
CONECT   29   19   26   46                                                  
CONECT   30   23   34   47                                                  
CONECT   31   20   25   57                                                  
CONECT   32   25   40   48                                                  
CONECT   33   27   42   49                                                  
CONECT   34   30   41   50                                                  
CONECT   35   26   51   56                                                  
CONECT   36   28   52   57                                                  
CONECT   37   38   39   44                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   27   32                                                       
CONECT   41   28   34                                                       
CONECT   42   33   53                                                       
CONECT   43   21   24   54                                                  
CONECT   44   22   37   55                                                  
CONECT   45   24                                                            
CONECT   46   29                                                            
CONECT   47   30                                                            
CONECT   48   32                                                            
CONECT   49   33                                                            
CONECT   50   34                                                            
CONECT   51   35                                                            
CONECT   52   36                                                            
CONECT   53   42                                                            
CONECT   54   43                                                            
CONECT   55   44                                                            
CONECT   56   23   35                                                       
CONECT   57   31   36                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  114    0
END

Synonyms

Not Available

Molecular Formula

C₃₇H₆₁N₇O₁₃

Average Mass

811.931

Monoisotopic Mass

811.432735052

IUPAC Name

3-[(2-{[1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene]amino}-5-(N-hydroxyformamido)pentanoyl)oxy]-N-[1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl]-2-methyltetradecanimidic acid

Traditional Name

3-[(2-{[1,2-dihydroxy-3-(2-hydroxybenzoyloxy)propylidene]amino}-5-(N-hydroxyformamido)pentanoyl)oxy]-N-[1-(dihydroxycarbonimidoyl)-4-(N-hydroxycarbamimidamido)butyl]-2-methyltetradecanimidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(N)=N)C(O)=NO

InChI Identifier

InChI=1S/C37H61N7O13/c1-3-4-5-6-7-8-9-10-11-20-31(25(2)32(48)40-27(33(49)42-53)17-15-22-44(55)37(38)39)57-36(52)28(18-14-21-43(54)24-45)41-34(50)30(47)23-56-35(51)26-16-12-13-19-29(26)46/h12-13,16,19,24-25,27-28,30-31,46-47,53-55H,3-11,14-15,17-18,20-23H2,1-2H3,(H3,38,39)(H,40,48)(H,41,50)(H,42,49)

InChI Key

JGIVUUUJEPUXSR-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Depsipeptides

Alternative Parents

Substituents

Depsipeptide
Arginine or derivatives
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
O-hydroxybenzoic acid ester
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Fatty amide
Monosaccharide
N-acyl-amine
N-hydroxyguanidine
Vinylogous acid
Secondary alcohol
Hydroxamic acid
Guanidine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Carboximidamide
Carboxylic acid derivative
Imine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen 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	0.012 g/L	ALOGPS
logP	2.57	ALOGPS
logP	3.5	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	10.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	324.94 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	217.03 m³·mol⁻¹	ChemAxon
Polarizability	86.34 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	462.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	118.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	697.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	629.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	615.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	146.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2631.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	605.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	273.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	328.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	90.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	167.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	238.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	66.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	225.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	266.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	525.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1678.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1287.8

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Asterobactin C_TMS_1	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O[Si](C)(C)C)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard non polar	2025-10-23	3844.1
Gas Chromatography	Asterobactin C_TMS_2	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(COC(=O)C1=CC=CC=C1O)O[Si](C)(C)C)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard non polar	2025-10-23	3889.67
Gas Chromatography	Asterobactin C_TMS_3	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O[Si](C)(C)C)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard non polar	2025-10-23	1176.23
Gas Chromatography	Asterobactin C_TMS_4	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(=NC(CCCN(O)C(=N)N)C(O)=NO)O[Si](C)(C)C	standard non polar	2025-10-23	2918.78
Gas Chromatography	Asterobactin C_TMS_5	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N)C(=NO)O[Si](C)(C)C	standard non polar	2025-10-23	1887.7
Gas Chromatography	Asterobactin C_TMS_6	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N[Si](C)(C)C)C(O)=NO	standard non polar	2025-10-23	715.325
Gas Chromatography	Asterobactin C_TMS_7	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(N)=N[Si](C)(C)C)C(O)=NO	standard non polar	2025-10-23	1123.88
Gas Chromatography	Asterobactin C_TMS_1	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O[Si](C)(C)C)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard polar	2025-10-23	4042.6
Gas Chromatography	Asterobactin C_TMS_2	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(COC(=O)C1=CC=CC=C1O)O[Si](C)(C)C)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard polar	2025-10-23	2390.79
Gas Chromatography	Asterobactin C_TMS_3	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O[Si](C)(C)C)C(C)C(O)=NC(CCCN(O)C(=N)N)C(O)=NO	standard polar	2025-10-23	2485.41
Gas Chromatography	Asterobactin C_TMS_4	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(=NC(CCCN(O)C(=N)N)C(O)=NO)O[Si](C)(C)C	standard polar	2025-10-23	4345.24
Gas Chromatography	Asterobactin C_TMS_5	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N)C(=NO)O[Si](C)(C)C	standard polar	2025-10-23	1700.65
Gas Chromatography	Asterobactin C_TMS_6	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(=N)N[Si](C)(C)C)C(O)=NO	standard polar	2025-10-23	2055.05
Gas Chromatography	Asterobactin C_TMS_7	CCCCCCCCCCCC(OC(=O)C(CCCN(O)C=O)N=C(O)C(O)COC(=O)C1=CC=CC=C1O)C(C)C(O)=NC(CCCN(O)C(N)=N[Si](C)(C)C)C(O)=NO	standard polar	2025-10-23	2807.38

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	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

78444754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583359

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 Asterobactin C (MMDBc0001787)

MOL for #<Metabolite:0x0000564323134fb8>

3D MOL for #<Metabolite:0x0000564323134fb8>

3D SDF for #<Metabolite:0x0000564323134fb8>

3D-SDF for #<Metabolite:0x0000564323134fb8>

PDB for #<Metabolite:0x0000564323134fb8>

3D PDB for #<Metabolite:0x0000564323134fb8>

SMILES for #<Metabolite:0x0000564323134fb8>

INCHI for #<Metabolite:0x0000564323134fb8>

Structure for #<Metabolite:0x0000564323134fb8>

3D Structure for #<Metabolite:0x0000564323134fb8>