NP-MRD: Showing NP-Card for 3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid (NP0310428)

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Record Information

Version

2.0

Created at

2022-09-11 05:44:01 UTC

Updated at

2022-09-11 05:44:01 UTC

NP-MRD ID

NP0310428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

Description

Surfactin A belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Surfactin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid was first documented in 2020 (PMID: 32828375). Based on a literature review a small amount of articles have been published on surfactin A (PMID: 34586599) (PMID: 33152809).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207442D          

 71 71  0  0  1  0            999 V2000
   -5.7649   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0504    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0504    1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3359   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1925    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4781   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0491   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654    0.3431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0356    0.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862    2.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9078    2.0999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.2418   -0.3525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3531   -1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7690   -0.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
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 13 14  1  4  0  0  0
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 16 22  1  0  0  0  0
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 11 71  1  0  0  0  0
M  END

     RDKit          3D

160160  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309112207442D          

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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  4  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  4  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  4  0  0  0
 38 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 41 45  1  0  0  0  0
 45 46  1  4  0  0  0
 45 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 48 53  1  0  0  0  0
 53 54  1  4  0  0  0
 53 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  6  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 56 61  1  0  0  0  0
 61 62  1  4  0  0  0
 61 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  6  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 64 69  1  0  0  0  0
 69 70  2  0  0  0  0
 69 71  1  0  0  0  0
 11 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCCCCC[C@@H]1CC(O)=N[C@@H](CCC(O)=O)C(O)=N[C@@H](CC(C)C)C(O)=N[C@H](CC(C)C)C(O)=N[C@@H](C(C)C)C(O)=N[C@@H](CC(O)=O)C(O)=N[C@H](CC(C)C)C(O)=N[C@@H](CC(C)C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C51H89N7O13/c1-28(2)18-16-14-13-15-17-19-34-26-41(59)52-35(20-21-42(60)61)45(64)53-36(22-29(3)4)46(65)55-38(24-31(7)8)49(68)58-44(33(11)12)50(69)56-39(27-43(62)63)48(67)54-37(23-30(5)6)47(66)57-40(25-32(9)10)51(70)71-34/h28-40,44H,13-27H2,1-12H3,(H,52,59)(H,53,64)(H,54,67)(H,55,65)(H,56,69)(H,57,66)(H,58,68)(H,60,61)(H,62,63)/t34-,35+,36+,37-,38-,39+,40+,44+/m1/s1

> <INCHI_KEY>
PBEDWPIWZYHNPL-RHKAOURMSA-N

> <FORMULA>
C51H89N7O13

> <MOLECULAR_WEIGHT>
1008.309

> <EXACT_MASS>
1007.651835954

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
112.10273668707293

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-12-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

> <JCHEM_LOGP>
11.089556411

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3144193667065034

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.90508722784865

> <JCHEM_POLAR_SURFACE_AREA>
329.03

> <JCHEM_REFRACTIVITY>
266.50100000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.761  -0.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.427   0.640   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.427   2.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.094  -0.130   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.760   0.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.426  -0.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.093   0.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.759  -0.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.425   0.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.092  -0.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.242   0.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.067   1.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.650   3.061   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.161   4.370   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.185   2.947   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.561   3.920   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.387   5.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.974   6.064   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.800   7.594   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.037   8.510   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.387   8.208   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.987   3.337   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.194   1.811   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       6.204   4.280   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.630   3.697   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.422   5.223   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.996   5.806   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.779   4.863   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.789   7.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.847   4.640   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.639   6.166   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0      10.273   4.057   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      11.490   5.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.282   6.526   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.500   7.468   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.292   8.994   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.925   6.886   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.915   4.417   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      14.133   5.360   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      13.123   2.891   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      14.549   2.308   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.766   3.251   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.192   2.668   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      15.558   4.777   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.756   0.782   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.182   0.199   0.000  0.00  0.00           O+0
HETATM   47  N   UNK     0      13.539  -0.161   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0      12.114   0.422   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      12.321  -1.104   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.747  -1.687   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      14.964  -0.744   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      13.955  -3.213   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      10.896  -0.521   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      11.104  -2.047   0.000  0.00  0.00           O+0
HETATM   55  N   UNK     0       9.471   0.062   0.000  0.00  0.00           N+0
HETATM   56  C   UNK     0       8.253  -0.881   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.461  -2.407   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       9.886  -2.990   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      11.425  -2.943   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.094  -4.516   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.828  -0.298   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       6.620   1.228   0.000  0.00  0.00           O+0
HETATM   63  N   UNK     0       5.610  -1.241   0.000  0.00  0.00           N+0
HETATM   64  C   UNK     0       4.185  -0.658   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       4.392  -2.184   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       5.818  -2.767   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       7.035  -1.824   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       6.026  -4.293   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       2.967  -1.601   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0       3.175  -3.127   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       1.542  -1.018   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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   12   71                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   45                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   41   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
CONECT   53   48   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   56   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64                                                       
CONECT   64   63   65   69                                                  
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66                                                            
CONECT   69   64   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   11                                                       
MASTER        0    0    0    0    0    0    0    0   71    0  142    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₈₉N₇O₁₃

Average Mass

1008.3090 Da

Monoisotopic Mass

1007.65184 Da

IUPAC Name

3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-12-(propan-2-yl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

Traditional Name

3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CCCCCCC[C@@H]1CC(O)=N[C@@H](CCC(O)=O)C(O)=N[C@@H](CC(C)C)C(O)=N[C@H](CC(C)C)C(O)=N[C@@H](C(C)C)C(O)=N[C@@H](CC(O)=O)C(O)=N[C@H](CC(C)C)C(O)=N[C@@H](CC(C)C)C(=O)O1

InChI Identifier

InChI=1S/C51H89N7O13/c1-28(2)18-16-14-13-15-17-19-34-26-41(59)52-35(20-21-42(60)61)45(64)53-36(22-29(3)4)46(65)55-38(24-31(7)8)49(68)58-44(33(11)12)50(69)56-39(27-43(62)63)48(67)54-37(23-30(5)6)47(66)57-40(25-32(9)10)51(70)71-34/h28-40,44H,13-27H2,1-12H3,(H,52,59)(H,53,64)(H,54,67)(H,55,65)(H,56,69)(H,57,66)(H,58,68)(H,60,61)(H,62,63)/t34-,35+,36+,37-,38-,39+,40+,44+/m1/s1

InChI Key

PBEDWPIWZYHNPL-RHKAOURMSA-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

Not Available

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

cyclodepsipeptide (CHEBI:71976 )
lipopeptide antibiotic (CHEBI:71976 )
macrocyclic lactone (CHEBI:71976 )

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	11.09	ChemAxon
pKa (Strongest Acidic)	2.91	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	329.03 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	266.5 m³·mol⁻¹	ChemAxon
Polarizability	112.1 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

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

28533730

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70789014

PDB ID

Not Available

ChEBI ID

71976

Good Scents ID

Not Available

References

General References

Vignesh M, Shankar SRM, MubarakAli D, Hari BNV: A Novel Rhizospheric Bacterium: Bacillus velezensis NKMV-3 as a Biocontrol Agent Against Alternaria Leaf Blight in Tomato. Appl Biochem Biotechnol. 2022 Jan;194(1):1-17. doi: 10.1007/s12010-021-03684-9. Epub 2021 Sep 29. [PubMed:34586599 ]
Pang L, Xia B, Liu X, Yi Y, Jiang L, Chen C, Li P, Zhang M, Deng X, Wang R: Improvement of antifungal activity of a culture filtrate of endophytic Bacillus amyloliquefaciens isolated from kiwifruit and its effect on postharvest quality of kiwifruit. J Food Biochem. 2021 Jan;45(1):e13551. doi: 10.1111/jfbc.13551. Epub 2020 Nov 5. [PubMed:33152809 ]
Jin P, Wang Y, Tan Z, Liu W, Miao W: Antibacterial activity and rice-induced resistance, mediated by C(15)surfactin A, in controlling rice disease caused by Xanthomonas oryzae pv. oryzae. Pestic Biochem Physiol. 2020 Oct;169:104669. doi: 10.1016/j.pestbp.2020.104669. Epub 2020 Jul 25. [PubMed:32828375 ]
LOTUS database [Link]

Showing NP-Card for 3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid (NP0310428)

MOL for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

3D MOL for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

3D SDF for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

3D-SDF for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

PDB for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

3D PDB for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

SMILES for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

INCHI for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

Structure for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)

3D Structure for NP0310428 (3-[(3s,6r,9s,12s,15r,18s,21s,25r)-9-(carboxymethyl)-5,8,11,14,17,20,23-heptahydroxy-12-isopropyl-25-(8-methylnonyl)-3,6,15,18-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,7,10,13,16,19,22-heptaen-21-yl]propanoic acid)