MiMeDB: Showing metabocard for Carboxymycobactin-4 (MMDBc0005968)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:22:31 UTC

Update Date

2025-10-07 16:05:05 UTC

Metabolite ID

MMDBc0005968

Metabolite Identification

Common Name

Carboxymycobactin-4

Description

Carboxymycobactin-4 is a siderophore, a type of iron-chelating compound produced by certain bacteria. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its properties and biological significance.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101222D          

 58 60  0  0  0  0            999 V2000
    1.7388    7.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    9.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8567   11.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    7.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204    9.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204   10.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060    9.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   11.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   12.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   13.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   14.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1397    5.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555    5.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132   12.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350    6.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421   14.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494   12.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3680    6.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   11.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   12.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    7.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   13.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494   13.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   10.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    9.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   12.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2783    7.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    7.5091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    9.5716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2628   11.2940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    8.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    7.3182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   13.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770    9.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2638   13.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   13.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    8.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    9.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1553    8.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    7.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    7.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278    7.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   12.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388    8.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204    8.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915    7.5091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 21  9  2  0  0  0  0
 22 10  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25  2  1  0  0  0  0
 26  3  1  0  0  0  0
 27 17  2  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  2  0  0  0  0
 30 27  1  0  0  0  0
 31  4  1  0  0  0  0
 31 25  1  0  0  0  0
 32 21  1  0  0  0  0
 33 22  1  0  0  0  0
 34 26  1  0  0  0  0
 35 25  1  0  0  0  0
 36 34  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 29  1  0  0  0  0
 40 28  1  4  0  0  0
 40 35  2  0  0  0  0
 41 29  1  4  0  0  0
 41 36  2  0  0  0  0
 42 34  1  0  0  0  0
 42 37  2  0  0  0  0
 43 23  1  0  0  0  0
 43 32  1  0  0  0  0
 44 24  1  0  0  0  0
 44 38  1  0  0  0  0
 45 30  1  0  0  0  0
 46 32  2  0  0  0  0
 47 33  2  0  0  0  0
 48 33  1  0  0  0  0
 49 35  1  0  0  0  0
 50 36  1  0  0  0  0
 51 38  2  0  0  0  0
 52 39  2  0  0  0  0
 53 43  1  0  0  0  0
 54 44  1  0  0  0  0
 55 26  1  0  0  0  0
 55 37  1  0  0  0  0
 56 31  1  0  0  0  0
 56 39  1  0  0  0  0
 57  9  1  0  0  0  0
 58 21  1  0  0  0  0
M  END


  Mrv1652305152101222D          

 58 60  0  0  0  0            999 V2000
    1.7388    7.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    9.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8567   11.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    7.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204    9.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204   10.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060    9.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   11.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   12.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   13.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   14.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1397    5.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9555    5.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132   12.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350    6.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421   14.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494   12.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3680    6.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   11.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   12.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    7.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   13.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770    8.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5494   13.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   10.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    9.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078   12.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2783    7.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    8.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    7.5091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    9.5716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2628   11.2940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    8.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    7.3182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   13.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770    9.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2638   13.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8349   13.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    8.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    9.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1553    8.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    7.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    7.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278    7.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8172   12.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388    8.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1204    8.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915    7.5091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 21  9  2  0  0  0  0
 22 10  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25  2  1  0  0  0  0
 26  3  1  0  0  0  0
 27 17  2  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  2  0  0  0  0
 30 27  1  0  0  0  0
 31  4  1  0  0  0  0
 31 25  1  0  0  0  0
 32 21  1  0  0  0  0
 33 22  1  0  0  0  0
 34 26  1  0  0  0  0
 35 25  1  0  0  0  0
 36 34  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 29  1  0  0  0  0
 40 28  1  4  0  0  0
 40 35  2  0  0  0  0
 41 29  1  4  0  0  0
 41 36  2  0  0  0  0
 42 34  1  0  0  0  0
 42 37  2  0  0  0  0
 43 23  1  0  0  0  0
 43 32  1  0  0  0  0
 44 24  1  0  0  0  0
 44 38  1  0  0  0  0
 45 30  1  0  0  0  0
 46 32  2  0  0  0  0
 47 33  2  0  0  0  0
 48 33  1  0  0  0  0
 49 35  1  0  0  0  0
 50 36  1  0  0  0  0
 51 38  2  0  0  0  0
 52 39  2  0  0  0  0
 53 43  1  0  0  0  0
 54 44  1  0  0  0  0
 55 26  1  0  0  0  0
 55 37  1  0  0  0  0
 56 31  1  0  0  0  0
 56 39  1  0  0  0  0
 57  9  1  0  0  0  0
 58 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005968

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCC(O)=O)=C(/[H])C(=O)N(O)CCCCC(N=C(O)C1N=C(OC1C)C1=CC=CC=C1O)C(=O)OC(CC)C(C)C(O)=NC1CCCCN(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H57N5O12/c1-4-31(25(2)35(49)40-28-18-13-16-24-44(54)38(28)51)56-39(52)29(41-36(50)34-26(3)55-37(42-34)27-17-11-12-20-30(27)45)19-14-15-23-43(53)32(46)21-9-7-5-6-8-10-22-33(47)48/h9,11-12,17,20-21,25-26,28-29,31,34,45,53-54H,4-8,10,13-16,18-19,22-24H2,1-3H3,(H,40,49)(H,41,50)(H,47,48)/b21-9-

> <INCHI_KEY>
PYSZFJPJQMRMAY-NKVSQWTQSA-N

> <FORMULA>
C39H57N5O12

> <MOLECULAR_WEIGHT>
787.908

> <EXACT_MASS>
787.400372295

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
85.09838675742577

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z)-9-{hydroxy[6-({1-[(1-hydroxy-2-oxoazepan-3-yl)-C-hydroxycarbonimidoyl]-1-methylbutan-2-yl}oxy)-5-({hydroxy[2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methylidene}amino)-6-oxohexyl]carbamoyl}non-8-enoic acid

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
6.09754931959503

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.7165928101503125

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1852289435193675

> <JCHEM_PKA_STRONGEST_BASIC>
1.4933587020536194

> <JCHEM_POLAR_SURFACE_AREA>
251.67999999999995

> <JCHEM_REFRACTIVITY>
204.26530000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z)-9-{hydroxy[6-({1-[(1-hydroxy-2-oxoazepan-3-yl)-C-hydroxycarbonimidoyl]-1-methylbutan-2-yl}oxy)-5-({hydroxy[2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methylidene}amino)-6-oxohexyl]carbamoyl}non-8-enoic 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       3.246  13.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.913  17.867   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.466  20.606   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.579  14.017   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.425  18.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.425  20.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.091  17.867   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.758  20.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.091  16.327   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.758  22.487   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.357  24.878   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.730  26.284   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.594  10.664   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.089  16.327   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.423  15.557   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.117  10.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.451  23.632   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.465  11.711   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.755  15.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.199  26.445   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.757  15.557   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.092  23.257   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.756  16.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.887  12.227   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.913  16.327   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.001  21.082   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.920  23.793   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.580  13.247   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.578  16.327   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.293  25.200   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.579  15.557   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.424  16.327   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -14.092  24.797   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.755  20.177   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.247  15.557   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.755  18.637   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.015  22.547   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.853  14.114   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.912  15.557   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0       7.247  14.017   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0       0.578  17.867   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0       0.491  21.082   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      -6.090  15.557   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      11.324  13.661   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0      -1.238  25.361   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -7.424  17.867   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -15.426  25.567   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -12.758  25.567   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       8.580  16.327   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -2.089  17.867   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       9.623  15.637   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       1.912  14.017   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -6.090  14.017   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      12.372  14.789   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -1.525  22.547   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       3.246  16.327   0.000  0.00  0.00           O+0
HETATM   57  H   UNK     0     -11.425  15.557   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      -8.757  14.017   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    1   31                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   21   57                                                  
CONECT   10    8   22                                                       
CONECT   11   12   17                                                       
CONECT   12   11   20                                                       
CONECT   13   16   18                                                       
CONECT   14   15   19                                                       
CONECT   15   14   23                                                       
CONECT   16   13   24                                                       
CONECT   17   11   27                                                       
CONECT   18   13   28                                                       
CONECT   19   14   29                                                       
CONECT   20   12   30                                                       
CONECT   21    9   32   58                                                  
CONECT   22   10   33                                                       
CONECT   23   15   43                                                       
CONECT   24   16   44                                                       
CONECT   25    2   31   35                                                  
CONECT   26    3   34   55                                                  
CONECT   27   17   30   37                                                  
CONECT   28   18   38   40                                                  
CONECT   29   19   39   41                                                  
CONECT   30   20   27   45                                                  
CONECT   31    4   25   56                                                  
CONECT   32   21   43   46                                                  
CONECT   33   22   47   48                                                  
CONECT   34   26   36   42                                                  
CONECT   35   25   40   49                                                  
CONECT   36   34   41   50                                                  
CONECT   37   27   42   55                                                  
CONECT   38   28   44   51                                                  
CONECT   39   29   52   56                                                  
CONECT   40   28   35                                                       
CONECT   41   29   36                                                       
CONECT   42   34   37                                                       
CONECT   43   23   32   53                                                  
CONECT   44   24   38   54                                                  
CONECT   45   30                                                            
CONECT   46   32                                                            
CONECT   47   33                                                            
CONECT   48   33                                                            
CONECT   49   35                                                            
CONECT   50   36                                                            
CONECT   51   38                                                            
CONECT   52   39                                                            
CONECT   53   43                                                            
CONECT   54   44                                                            
CONECT   55   26   37                                                       
CONECT   56   31   39                                                       
CONECT   57    9                                                            
CONECT   58   21                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

Synonyms

Not Available

Molecular Formula

C₃₉H₅₇N₅O₁₂

Average Mass

787.908

Monoisotopic Mass

787.400372295

IUPAC Name

(8Z)-9-{hydroxy[6-({1-[(1-hydroxy-2-oxoazepan-3-yl)-C-hydroxycarbonimidoyl]-1-methylbutan-2-yl}oxy)-5-({hydroxy[2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methylidene}amino)-6-oxohexyl]carbamoyl}non-8-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCC(O)=O)=C(/[H])C(=O)N(O)CCCCC(N=C(O)C1N=C(OC1C)C1=CC=CC=C1O)C(=O)OC(CC)C(C)C(O)=NC1CCCCN(O)C1=O

InChI Identifier

InChI=1S/C39H57N5O12/c1-4-31(25(2)35(49)40-28-18-13-16-24-44(54)38(28)51)56-39(52)29(41-36(50)34-26(3)55-37(42-34)27-17-11-12-20-30(27)45)19-14-15-23-43(53)32(46)21-9-7-5-6-8-10-22-33(47)48/h9,11-12,17,20-21,25-26,28-29,31,34,45,53-54H,4-8,10,13-16,18-19,22-24H2,1-3H3,(H,40,49)(H,41,50)(H,47,48)/b21-9-

InChI Key

PYSZFJPJQMRMAY-NKVSQWTQSA-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
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Caprolactam
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Azepane
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Fatty amide
N-acyl-amine
Benzenoid
Dicarboxylic acid or derivatives
Oxazoline
Carboxamide group
Carboxylic acid ester
Hydroxamic acid
Lactam
Secondary carboxylic acid amide
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0072 g/L	ALOGPS
logP	3.41	ALOGPS
logP	6.1	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	1.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	251.68 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	204.27 m³·mol⁻¹	ChemAxon
Polarizability	85.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

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	193.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	87.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	825.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	825.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	847.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	156.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	4003.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	117.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	373.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	540.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	82.5
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	270.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	14.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	216.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	283.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	562.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2278.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1692.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Carboxymycobactin-4_TMS_1	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O[Si](C)(C)C)N=C(O)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard non polar	2025-10-23	3698.53
Gas Chromatography	Carboxymycobactin-4_TMS_2	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O[Si](C)(C)C)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard non polar	2025-10-23	3357.8
Gas Chromatography	Carboxymycobactin-4_TMS_3	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O)C1N=C(C2=CC=CC=C2O[Si](C)(C)C)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard non polar	2025-10-23	923.825
Gas Chromatography	Carboxymycobactin-4_TMS_4	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(=NC1CCCCN(O)C1=O)O[Si](C)(C)C	standard non polar	2025-10-23	2100.48
Gas Chromatography	Carboxymycobactin-4_TMS_1	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O[Si](C)(C)C)N=C(O)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard polar	2025-10-23	2877.59
Gas Chromatography	Carboxymycobactin-4_TMS_2	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O[Si](C)(C)C)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard polar	2025-10-23	2354.93
Gas Chromatography	Carboxymycobactin-4_TMS_3	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O)C1N=C(C2=CC=CC=C2O[Si](C)(C)C)OC1C)C(C)C(O)=NC1CCCCN(O)C1=O	standard polar	2025-10-23	1290.03
Gas Chromatography	Carboxymycobactin-4_TMS_4	CCC(OC(=O)C(CCCCN(O)C(=O)/C=C\CCCCCCC(=O)O)N=C(O)C1N=C(C2=CC=CC=C2O)OC1C)C(C)C(=NC1CCCCN(O)C1=O)O[Si](C)(C)C	standard polar	2025-10-23	296.478

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

78444015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584580

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 Carboxymycobactin-4 (MMDBc0005968)

MOL for #<Metabolite:0x00007f9ac9b00a48>

3D MOL for #<Metabolite:0x00007f9ac9b00a48>

3D SDF for #<Metabolite:0x00007f9ac9b00a48>

3D-SDF for #<Metabolite:0x00007f9ac9b00a48>

PDB for #<Metabolite:0x00007f9ac9b00a48>

3D PDB for #<Metabolite:0x00007f9ac9b00a48>

SMILES for #<Metabolite:0x00007f9ac9b00a48>

INCHI for #<Metabolite:0x00007f9ac9b00a48>

Structure for #<Metabolite:0x00007f9ac9b00a48>

3D Structure for #<Metabolite:0x00007f9ac9b00a48>