NP-MRD: Showing NP-Card for (9z)-10-{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}dec-9-enoic acid (NP0329916)

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Record Information

Version

2.0

Created at

2022-09-12 14:46:51 UTC

Updated at

2022-09-12 14:46:51 UTC

NP-MRD ID

NP0329916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9z)-10-{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}dec-9-enoic acid

Description

Carboxymycobactin 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. (9z)-10-{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}dec-9-enoic acid is found in Mycobacterium avium. (9z)-10-{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}dec-9-enoic acid was first documented in 2016 (PMID: 27566542). Based on a literature review a significant number of articles have been published on Carboxymycobactin (PMID: 33609202) (PMID: 32472729) (PMID: 32296173) (PMID: 31945239) (PMID: 28231453).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216462D          

 57 59  0  0  0  0            999 V2000
   10.1333  -11.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4188  -10.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4188   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7043   -9.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9899   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9899  -10.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5609   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -9.9239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030  -10.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -9.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8451   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1307   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2983   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1562   -8.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -7.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754   -8.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5609   -8.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464   -8.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5609   -7.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2284   -6.9640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9734   -6.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4583   -5.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1228   -4.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6077   -4.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4282   -4.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7637   -4.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2788   -5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6144   -6.3519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484   -6.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8935   -6.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1089   -7.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1333   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1333   -8.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477  -10.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5622   -9.5114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2767   -9.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9583   -9.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7467   -9.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0481  -10.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6356  -11.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8198  -11.3078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5766  -12.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2150  -10.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4471  -11.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 28  7  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
  3 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 48 49  1  4  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 49 56  1  0  0  0  0
 56 57  2  0  0  0  0
M  END

     RDKit          3D

116118  0  0  0  0  0  0  0  0999 V2000
    2.2675   -1.3695    1.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7933   -2.5074    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1443   -0.8881    2.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8665    0.6410    0.9988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5800    1.5505   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148    2.2670   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9690    1.5429   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    2.5642   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3707    1.9553   -0.7208 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053    1.5090    0.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947    1.7919   -2.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    2.1661   -2.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1898    1.2394   -2.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    1.0618   -3.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417    1.4260   -4.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    0.4616   -5.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4971   -0.7630   -5.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6881   -1.9500   -5.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483   -1.9826   -3.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -1.6494   -3.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0605   -2.6541   -3.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761   -2.3258   -3.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3690   -1.3671   -2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -3.0976   -3.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922    1.5164    2.2044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7823    1.2627    3.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767    0.1404    3.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2834    3.9929    4.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944    3.6942    5.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    4.5414    5.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    5.7460    5.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3223    6.0781    4.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    5.1935    4.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418    5.5288    3.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    1.8381    5.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836    1.5461    5.6201 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5338    0.0667    5.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1387   -3.8095    0.3746 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4640   -4.9717    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542   -4.0252    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386   -5.3273   -0.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -3.1291    0.2853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8480   -3.3108    0.0736 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.3801    2.3790   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    1.1024   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1750    0.9620    0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    3.3711   -1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1650    3.0453    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308    1.9278    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    0.9065   -1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8783    0.6091   -3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1330    2.2215   -5.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4549   -4.0937   -3.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5855    0.1749    3.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8541    2.6136    4.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3434    4.3138    6.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0329916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(OC(=O)C(CCCCN(O)C(=O)\C=C/CCCCCCCC(O)=O)N=C(O)C1N=C(OC1C)C1=CC=CC=C1O)C(C)C(O)=NC1CCCCN(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H59N5O12/c1-4-32(26(2)36(50)41-29-19-14-17-25-45(55)39(29)52)57-40(53)30(42-37(51)35-27(3)56-38(43-35)28-18-12-13-21-31(28)46)20-15-16-24-44(54)33(47)22-10-8-6-5-7-9-11-23-34(48)49/h10,12-13,18,21-22,26-27,29-30,32,35,46,54-55H,4-9,11,14-17,19-20,23-25H2,1-3H3,(H,41,50)(H,42,51)(H,48,49)/b22-10-

> <INCHI_KEY>
GBGPUWKHRHOTOT-YVNNLAQVSA-N

> <FORMULA>
C40H59N5O12

> <MOLECULAR_WEIGHT>
801.935

> <EXACT_MASS>
801.41602236

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
86.54317391582333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-10-{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}dec-9-enoic acid

> <JCHEM_LOGP>
6.5421530058253925

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.7344008123247745

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1857557703641306

> <JCHEM_PKA_STRONGEST_BASIC>
1.4933681578378388

> <JCHEM_POLAR_SURFACE_AREA>
251.67999999999995

> <JCHEM_REFRACTIVITY>
208.8663000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9Z)-10-{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}dec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      18.915 -20.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.582 -20.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.582 -18.525   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      16.248 -17.755   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.914 -18.525   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.914 -20.065   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.581 -17.755   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.247 -18.525   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.913 -17.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.580 -18.525   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.246 -17.755   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.912 -18.525   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.912 -20.065   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.579 -17.755   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.245 -18.525   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.579 -16.215   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.245 -15.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.911 -16.215   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.578 -15.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.244 -16.215   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.090 -15.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.423 -16.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.757 -15.445   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.091 -16.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.424 -15.445   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.758 -16.215   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.424 -13.905   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      13.581 -16.215   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      12.247 -15.445   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.913 -16.215   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.247 -13.905   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      13.493 -13.000   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      13.017 -11.535   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.922 -10.289   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.296  -8.882   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.201  -7.636   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.733  -7.797   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.359  -9.204   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.454 -10.450   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      16.080 -11.857   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      11.477 -11.535   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      11.001 -13.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.537 -13.475   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.915 -17.755   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.915 -16.215   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      20.249 -18.525   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      20.249 -20.065   0.000  0.00  0.00           O+0
HETATM   48  N   UNK     0      21.583 -17.755   0.000  0.00  0.00           N+0
HETATM   49  C   UNK     0      22.916 -18.525   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      24.189 -17.657   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      25.660 -18.111   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.223 -19.545   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      25.453 -20.878   0.000  0.00  0.00           C+0
HETATM   54  N   UNK     0      23.930 -21.108   0.000  0.00  0.00           N+0
HETATM   55  O   UNK     0      23.476 -22.579   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      22.801 -20.060   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      21.368 -20.623   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   44                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    7   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   42                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34   40                                                  
CONECT   40   39                                                            
CONECT   41   33   42                                                       
CONECT   42   41   31   43                                                  
CONECT   43   42                                                            
CONECT   44    3   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50   56                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   49   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₅₉N₅O₁₂

Average Mass

801.9350 Da

Monoisotopic Mass

801.41602 Da

IUPAC Name

(9Z)-10-{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}dec-9-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(OC(=O)C(CCCCN(O)C(=O)\C=C/CCCCCCCC(O)=O)N=C(O)C1N=C(OC1C)C1=CC=CC=C1O)C(C)C(O)=NC1CCCCN(O)C1=O

InChI Identifier

InChI=1S/C40H59N5O12/c1-4-32(26(2)36(50)41-29-19-14-17-25-45(55)39(29)52)57-40(53)30(42-37(51)35-27(3)56-38(43-35)28-18-12-13-21-31(28)46)20-15-16-24-44(54)33(47)22-10-8-6-5-7-9-11-23-34(48)49/h10,12-13,18,21-22,26-27,29-30,32,35,46,54-55H,4-9,11,14-17,19-20,23-25H2,1-3H3,(H,41,50)(H,42,51)(H,48,49)/b22-10-

InChI Key

GBGPUWKHRHOTOT-YVNNLAQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mycobacterium avium	LOTUS Database	35616633

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.54	ChemAxon
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	24	ChemAxon
Refractivity	208.87 m³·mol⁻¹	ChemAxon
Polarizability	86.54 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444276

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Choudhury M, Koduru TN, Kumar N, Salimi S, Desai K, Prabhu NP, Sritharan M: Iron uptake and transport by the carboxymycobactin-mycobactin siderophore machinery of Mycobacterium tuberculosis is dependent on the iron-regulated protein HupB. Biometals. 2021 Jun;34(3):511-528. doi: 10.1007/s10534-021-00292-2. Epub 2021 Feb 20. [PubMed:33609202 ]
Kumar N, Sritharan M: Role of a 21-kDa iron-regulated protein IrpA in the uptake of ferri-exochelin by Mycobacterium smegmatis. J Appl Microbiol. 2020 Dec;129(6):1733-1743. doi: 10.1111/jam.14728. Epub 2020 Jun 25. [PubMed:32472729 ]
Arnold FM, Weber MS, Gonda I, Gallenito MJ, Adenau S, Egloff P, Zimmermann I, Hutter CAJ, Hurlimann LM, Peters EE, Piel J, Meloni G, Medalia O, Seeger MA: The ABC exporter IrtAB imports and reduces mycobacterial siderophores. Nature. 2020 Apr;580(7803):413-417. doi: 10.1038/s41586-020-2136-9. Epub 2020 Mar 25. [PubMed:32296173 ]
Knobloch P, Koliwer-Brandl H, Arnold FM, Hanna N, Gonda I, Adenau S, Personnic N, Barisch C, Seeger MA, Soldati T, Hilbi H: Mycobacterium marinum produces distinct mycobactin and carboxymycobactin siderophores to promote growth in broth and phagocytes. Cell Microbiol. 2020 May;22(5):e13163. doi: 10.1111/cmi.13163. Epub 2020 Feb 11. [PubMed:31945239 ]
Sandhu P, Akhter Y: Siderophore transport by MmpL5-MmpS5 protein complex in Mycobacterium tuberculosis. J Inorg Biochem. 2017 May;170:75-84. doi: 10.1016/j.jinorgbio.2017.02.013. Epub 2017 Feb 14. [PubMed:28231453 ]
Vergnolle O, Xu H, Tufariello JM, Favrot L, Malek AA, Jacobs WR Jr, Blanchard JS: Post-translational Acetylation of MbtA Modulates Mycobacterial Siderophore Biosynthesis. J Biol Chem. 2016 Oct 14;291(42):22315-22326. doi: 10.1074/jbc.M116.744532. Epub 2016 Aug 26. [PubMed:27566542 ]
LOTUS database [Link]

Showing NP-Card for (9z)-10-{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}dec-9-enoic acid (NP0329916)

MOL for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

3D MOL for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

3D SDF for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

3D-SDF for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

PDB for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

3D PDB for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

SMILES for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

INCHI for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

Structure for NP0329916 ((9z)-10-{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}dec-9-enoic acid)

3D Structure for NP0329916 ((9z)-10-{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}dec-9-enoic acid)