NP-MRD: Showing NP-Card for melleumin A (NP0027840)

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Record Information

Version

2.0

Created at

2021-06-19 19:53:19 UTC

Updated at

2021-06-29 23:54:13 UTC

NP-MRD ID

NP0027840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

melleumin A

Provided By

JEOL Database JEOL Logo

Description

melleumin A is found in Physarum melleum. melleumin A was first documented in 2008 (PMID: 18032042). Based on a literature review a small amount of articles have been published on Melleumin A (PMID: 20865179) (PMID: 19072738) (PMID: 21467667).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121533D          

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     RDKit          3D

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M  END


  Mrv1652306192121533D          

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M  END
> <DATABASE_ID>
NP0027840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[C@]1([H])N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C2=C([H])C([H])=C(OC([H])([H])[H])C([H])=C2[H])[C@]([H])(OC(=O)C([H])([H])[C@]1([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H29N3O8/c1-14-23(28-24(33)16-5-9-18(35-2)10-6-16)25(34)26-13-21(31)27-19(20(30)12-22(32)36-14)11-15-3-7-17(29)8-4-15/h3-10,14,19-20,23,29-30H,11-13H2,1-2H3,(H,26,34)(H,27,31)(H,28,33)/t14-,19+,20+,23+/m1/s1

> <INCHI_KEY>
BTCSAJYXUASTSJ-NRLVQOBCSA-N

> <FORMULA>
C25H29N3O8

> <MOLECULAR_WEIGHT>
499.52

> <EXACT_MASS>
499.195464906

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.61586583842206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3S,9S,10S)-10-hydroxy-9-[(4-hydroxyphenyl)methyl]-2-methyl-4,7,12-trioxo-1-oxa-5,8-diazacyclododecan-3-yl]-4-methoxybenzamide

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.13622202933333435

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.088524933553947

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.485603035589932

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1642818581125738

> <JCHEM_POLAR_SURFACE_AREA>
163.29

> <JCHEM_REFRACTIVITY>
126.83270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3S,9S,10S)-10-hydroxy-9-[(4-hydroxyphenyl)methyl]-2-methyl-4,7,12-trioxo-1-oxa-5,8-diazacyclododecan-3-yl]-4-methoxybenzamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
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 24 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.028  -7.907   1.529  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.392  -7.739   0.268  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.680  -6.588   0.081  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.078  -6.472  -1.175  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.320  -5.344  -1.500  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.163  -4.311  -0.571  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.655  -3.129  -0.964  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.493  -3.217  -1.855  0.00  0.00           O+0
HETATM    9  N   UNK     0      -0.408  -1.952  -0.300  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.153  -0.728  -0.599  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.343   0.448  -0.008  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.344   0.289   1.007  0.00  0.00           O+0
HETATM   13  N   UNK     0      -0.405   1.692  -0.566  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.000   2.091  -1.831  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.686   3.462  -1.896  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.592   4.149  -2.918  0.00  0.00           O+0
HETATM   17  N   UNK     0      -2.552   3.889  -0.940  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.948   3.334   0.362  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.555   4.317   1.491  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.056   4.432   1.663  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.340   5.442   1.004  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.049   5.524   1.125  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.723   4.592   1.906  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.078   4.631   2.046  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.031   3.585   2.566  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.357   3.505   2.449  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.483   3.064   0.387  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.168   4.306   0.160  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.959   2.040  -0.647  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.569   0.642  -0.249  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.330  -0.172   0.248  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.248   0.459  -0.479  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.596  -0.750  -0.027  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.614  -0.833   1.504  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.752  -4.431   0.694  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.510  -5.566   1.016  0.00  0.00           C+0
HETATM   37  H   UNK     0       3.771  -7.122   1.704  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.555  -8.866   1.513  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.293  -7.945   2.339  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.199  -7.268  -1.906  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.143  -5.276  -2.482  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.347  -1.866   0.372  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.184  -0.629  -1.688  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.148   2.390  -0.076  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.719   1.351  -2.183  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.172   2.106  -2.549  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.999   4.768  -1.183  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.424   2.400   0.540  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.986   3.983   2.444  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.973   5.314   1.303  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.861   6.168   0.382  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.581   6.313   0.603  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.420   5.396   1.554  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.571   2.857   3.166  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.882   2.703   2.964  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.761   2.723   1.392  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.123   4.146   0.267  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.053   2.068  -0.730  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.592   2.258  -1.656  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.137  -1.608  -0.443  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.630  -0.994   1.877  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.000  -1.661   1.873  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.267   0.101   1.959  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.616  -3.670   1.456  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.948  -5.621   2.007  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1                                                       
CONECT    3    4   36    2                                                  
CONECT    4    5    3   40                                                  
CONECT    5    6    4   41                                                  
CONECT    6    7    5   35                                                  
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   42                                                  
CONECT   10   33   11    9   43                                             
CONECT   11   13   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14   11   44                                                  
CONECT   14   15   13   45   46                                             
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18   15   47                                                  
CONECT   18   27   17   19   48                                             
CONECT   19   18   20   49   50                                             
CONECT   20   19   21   26                                                  
CONECT   21   20   22   51                                                  
CONECT   22   21   23   52                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23   53                                                       
CONECT   25   23   26   54                                                  
CONECT   26   25   20   55                                                  
CONECT   27   18   28   29   56                                             
CONECT   28   27   57                                                       
CONECT   29   30   27   58   59                                             
CONECT   30   32   29   31                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   34   32   10   60                                             
CONECT   34   33   61   62   63                                             
CONECT   35   36    6   64                                                  
CONECT   36    3   35   65                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   33                                                            
CONECT   61   34                                                            
CONECT   62   34                                                            
CONECT   63   34                                                            
CONECT   64   35                                                            
CONECT   65   36                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  134    0
END

RDKit          3D

65 67  0  0  0  0  0  0  0  0999 V2000
    3.0279   -7.9074    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -7.7394    0.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -6.5880    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -6.4718   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203   -5.3442   -1.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1625   -4.3107   -0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6554   -3.1294   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -3.2168   -1.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082   -1.9521   -0.3004 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -0.7282   -0.5987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3431    0.4480   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440    0.2888    1.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4052    1.6923   -0.5655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.0905   -1.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855    3.4615   -1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924    4.1491   -2.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5519    3.8894   -0.9400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481    3.3341    0.3616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5548    4.3169    1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    4.4317    1.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400    5.4418    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    5.5241    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    4.5924    1.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781    4.6313    2.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    3.5849    2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    3.5046    2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4829    3.0642    0.3872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1682    4.3061    0.1598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    2.0402   -0.6471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5688    0.6422   -0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -0.1721    0.2477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480    0.4590   -0.4791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5959   -0.7504   -0.0268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6137   -0.8332    1.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516   -4.4315    0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102   -5.5655    1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7708   -7.1223    1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546   -8.8664    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925   -7.9448    2.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -7.2677   -1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -5.2756   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474   -1.8663    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1839   -0.6285   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482    2.3901   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    1.3510   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1718    2.1061   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985    4.7683   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243    2.3996    0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    3.9830    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9729    5.3143    1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613    6.1675    0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5806    6.3133    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4195    5.3960    1.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712    2.8569    3.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815    2.7027    2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7609    2.7232    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235    4.1462    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0532    2.0684   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5924    2.2577   -1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371   -1.6083   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298   -0.9941    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -1.6606    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672    0.1005    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6157   -3.6700    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483   -5.6210    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
 33 34  1  0
  7  6  1  0
 32 30  1  0
  7  8  2  0
  6  5  2  0
 33 32  1  0
  5  4  1  0
 30 29  1  0
  4  3  2  0
 27 18  1  0
  3 36  1  0
 18 17  1  0
 36 35  2  0
 35  6  1  0
 17 15  1  0
  3  2  1  0
 15 14  1  0
  2  1  1  0
 33 10  1  0
 18 19  1  0
 27 28  1  0
 19 20  1  0
 14 13  1  0
 20 21  2  0
 30 31  2  0
 21 22  1  0
 13 11  1  0
 22 23  2  0
 15 16  2  0
 23 25  1  0
 11 10  1  0
 25 26  2  0
 26 20  1  0
 10  9  1  0
 23 24  1  0
 29 27  1  0
 11 12  2  0
 29 58  1  0
 29 59  1  0
 33 60  1  6
 13 44  1  0
 10 43  1  6
 34 61  1  0
 34 62  1  0
 34 63  1  0
 27 56  1  1
 18 48  1  1
 17 47  1  0
 14 45  1  0
 14 46  1  0
 28 57  1  0
  9 42  1  0
  5 41  1  0
  4 40  1  0
 36 65  1  0
 35 64  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 22 52  1  0
 25 54  1  0
 26 55  1  0
 24 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₉N₃O₈

Average Mass

499.5200 Da

Monoisotopic Mass

499.19546 Da

IUPAC Name

N-[(2R,3S,9S,10S)-10-hydroxy-9-[(4-hydroxyphenyl)methyl]-2-methyl-4,7,12-trioxo-1-oxa-5,8-diazacyclododecan-3-yl]-4-methoxybenzamide

Traditional Name

N-[(2R,3S,9S,10S)-10-hydroxy-9-[(4-hydroxyphenyl)methyl]-2-methyl-4,7,12-trioxo-1-oxa-5,8-diazacyclododecan-3-yl]-4-methoxybenzamide

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[C@]1([H])N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C2=C([H])C([H])=C(OC([H])([H])[H])C([H])=C2[H])[C@]([H])(OC(=O)C([H])([H])[C@]1([H])O[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H29N3O8/c1-14-23(28-24(33)16-5-9-18(35-2)10-6-16)25(34)26-13-21(31)27-19(20(30)12-22(32)36-14)11-15-3-7-17(29)8-4-15/h3-10,14,19-20,23,29-30H,11-13H2,1-2H3,(H,26,34)(H,27,31)(H,28,33)/t14-,19+,20+,23+/m1/s1

InChI Key

BTCSAJYXUASTSJ-NRLVQOBCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Physarum melleum	JEOL database	Nakatani, S., et al, Tetrahedron Letts. 46, 267 (2005)

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

Alpha-dipeptide
Cyclic depsipeptide
N-acyl-alpha amino acid or derivatives
Macrolactam
Alpha-amino acid or derivatives
Benzoic acid or derivatives
Benzamide
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.45	ALOGPS
logP	0.14	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	163.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.83 m³·mol⁻¹	ChemAxon
Polarizability	50.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

28288282

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50901467

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arai MA, Hanazawa S, Uchino Y, Li X, Ishibashi M: Total synthesis and evaluation of Wnt signal inhibition of melleumin A and B, and their derivatives. Org Biomol Chem. 2010 Dec 7;8(23):5285-93. doi: 10.1039/c0ob00352b. Epub 2010 Sep 23. [PubMed:20865179 ]
Luo JM, Dai CF, Lin SY, Huang PQ: Asymmetric syntheses and Wnt signal inhibitory activity of melleumin A and four analogues of melleumins A and B. Chem Asian J. 2009 Feb 2;4(2):328-35. doi: 10.1002/asia.200800355. [PubMed:19072738 ]
Hanazawa S, Arai MA, Li X, Ishibashi M: Determination of absolute stereochemistry, total synthesis, and evaluation of peptides from the myxomycete Physarum melleum. Bioorg Med Chem Lett. 2008 Jan 1;18(1):95-8. doi: 10.1016/j.bmcl.2007.11.005. Epub 2007 Nov 5. [PubMed:18032042 ]
Arai MA: Approaches to neural stem cells and cancer cells based on natural products. Chem Pharm Bull (Tokyo). 2011;59(4):417-26. doi: 10.1248/cpb.59.417. [PubMed:21467667 ]
Nakatani, S., et al. (2005). Nakatani, S., et al, Tetrahedron Letts. 46, 267 (2005). Tetrahedron Lett.

Showing NP-Card for melleumin A (NP0027840)

MOL for NP0027840 (melleumin A)

3D MOL for NP0027840 (melleumin A)

3D SDF for NP0027840 (melleumin A)

3D-SDF for NP0027840 (melleumin A)

PDB for NP0027840 (melleumin A)

3D PDB for NP0027840 (melleumin A)

SMILES for NP0027840 (melleumin A)

INCHI for NP0027840 (melleumin A)

Structure for NP0027840 (melleumin A)

3D Structure for NP0027840 (melleumin A)