NP-MRD: Showing NP-Card for Asperterrestide A (NP0011890)

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Record Information

Version

2.0

Created at

2021-01-05 21:26:27 UTC

Updated at

2021-07-15 17:10:15 UTC

NP-MRD ID

NP0011890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperterrestide A

Provided By

NPAtlas

Description

Asperterrestide A belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Asperterrestide A is found in Aspergillus. Asperterrestide A was first documented in 2013 (PMID: 23806112). Based on a literature review a small amount of articles have been published on Asperterrestide A (PMID: 31070032) (PMID: 24562325).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117003D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117003D          

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 33 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])[C@@]1([H])N(C(=O)[C@]([H])(N([H])C(=O)[C@]([H])(N([H])C(=O)C2=C([H])C([H])=C([H])C([H])=C2N([H])C1=O)C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N4O5/c1-5-15(2)20-26(35)30(4)21(22(31)17-11-7-6-8-12-17)25(34)28-19-14-10-9-13-18(19)24(33)27-16(3)23(32)29-20/h6-16,20-22,31H,5H2,1-4H3,(H,27,33)(H,28,34)(H,29,32)/t15-,16+,20+,21+,22-/m0/s1

> <INCHI_KEY>
AQBNNSWAQPPMPF-QZPRSPPASA-N

> <FORMULA>
C26H32N4O5

> <MOLECULAR_WEIGHT>
480.565

> <EXACT_MASS>
480.237270146

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.36210065979962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6R,9R)-6-[(2S)-butan-2-yl]-3-[(S)-hydroxy(phenyl)methyl]-4,9-dimethyl-2,3,4,5,6,7,8,9,10,11-decahydro-1H-1,4,7,10-benzotetrazacyclotridecine-2,5,8,11-tetrone

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
2.4253979863333335

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.393241233363076

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.793058307532434

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6330001050989957

> <JCHEM_POLAR_SURFACE_AREA>
127.84

> <JCHEM_REFRACTIVITY>
131.74550000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6R,9R)-6-[(2S)-butan-2-yl]-3-[(S)-hydroxy(phenyl)methyl]-4,9-dimethyl-1,3,6,7,9,10-hexahydro-1,4,7,10-benzotetrazacyclotridecine-2,5,8,11-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
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 10 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 15 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 20 56  1  0
 23 57  1  6
 24 58  1  6
 25 59  1  0
 27 60  1  0
 28 61  1  0
 29 62  1  0
 30 63  1  0
 31 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.532  -3.203  -2.671  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.468  -2.438  -1.911  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.165  -1.630  -0.843  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.127  -0.701  -1.562  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.199  -0.810  -0.023  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.968  -0.081   0.965  0.00  0.00           N+0
HETATM    7  C   UNK     0      -2.551   1.175   1.413  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.787   1.504   2.622  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.839   2.202   0.608  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.934   3.133   0.112  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.838   2.863   1.413  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.087   3.846   0.979  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.002   5.009   1.571  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.122   3.730  -0.043  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.057   4.744  -1.024  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.987   4.778  -2.034  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.970   3.817  -2.067  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.061   2.819  -1.127  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.113   2.770  -0.085  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.333   1.721   0.845  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.462   0.690   1.281  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.165   0.707   2.534  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.887  -0.376   0.423  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.870  -1.231  -0.291  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.741  -0.461  -1.086  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.705  -2.108   0.561  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.371  -3.421   0.753  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.164  -4.221   1.540  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.306  -3.723   2.150  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.621  -2.382   1.936  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.821  -1.601   1.150  0.00  0.00           C+0
HETATM   32  N   UNK     0       0.020  -1.216   1.212  0.00  0.00           N+0
HETATM   33  C   UNK     0       0.404  -1.663   2.537  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.259  -1.664   0.748  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.640  -2.838   0.988  0.00  0.00           O+0
HETATM   36  H   UNK     0      -3.787  -2.687  -3.612  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.176  -4.227  -2.962  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.451  -3.355  -2.096  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.762  -3.184  -1.493  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.867  -1.776  -2.579  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.777  -2.329  -0.242  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.566  -1.244  -2.405  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.591   0.173  -1.991  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.926  -0.367  -0.870  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.667  -0.156  -0.719  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.846  -0.547   1.321  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.352   1.815  -0.296  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.118   3.901   0.891  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.886   2.589  -0.028  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.667   3.614  -0.843  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.791   2.596   2.443  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.301   5.522  -1.004  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.917   5.570  -2.783  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.697   3.873  -2.887  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.875   2.112  -1.216  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.322   1.675   1.313  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.288   0.147  -0.378  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.336  -1.883  -1.013  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.285  -0.080  -1.874  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.462  -3.853   0.278  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.883  -5.274   1.685  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.894  -4.380   2.754  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.529  -2.002   2.428  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.123  -0.563   1.023  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.055  -2.732   2.615  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.158  -1.131   3.339  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.462  -1.562   2.774  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3   39   40                                             
CONECT    3    2    4    5   41                                             
CONECT    4    3   42   43   44                                             
CONECT    5    3    6   34   45                                             
CONECT    6    5    7   46                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   47                                             
CONECT   10    9   48   49   50                                             
CONECT   11    9   12   51                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   52                                                  
CONECT   16   15   17   53                                                  
CONECT   17   16   18   54                                                  
CONECT   18   17   19   55                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   56                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   32   57                                             
CONECT   24   23   25   26   58                                             
CONECT   25   24   59                                                       
CONECT   26   24   27   31                                                  
CONECT   27   26   28   60                                                  
CONECT   28   27   29   61                                                  
CONECT   29   28   30   62                                                  
CONECT   30   29   31   63                                                  
CONECT   31   30   26   64                                                  
CONECT   32   23   33   34                                                  
CONECT   33   32   65   66   67                                             
CONECT   34   32   35    5                                                  
CONECT   35   34                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    2                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   11                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   20                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   33                                                            
CONECT   67   33                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  138    0
END

RDKit          3D

67 69  0  0  0  0  0  0  0  0999 V2000
   -3.5319   -3.2025   -2.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683   -2.4380   -1.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648   -1.6304   -0.8434 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1267   -0.7007   -1.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991   -0.8095   -0.0227 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.5507    1.1751    1.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7870    1.5037    2.6215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8393    2.2024    0.6075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9337    3.1329    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376    2.8632    1.4127 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    3.8464    0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0015    5.0087    1.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    3.7303   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568    4.7444   -1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9871    4.7783   -2.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9695    3.8173   -2.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0608    2.8190   -1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1128    2.7704   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    1.7211    0.8448 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615    0.6902    1.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    0.7074    2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -0.3758    0.4234 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8703   -1.2312   -0.2910 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.3707   -3.4207    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638   -4.2207    1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -3.7234    2.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -2.3816    1.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8208   -1.6011    1.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199   -1.2156    1.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2586   -1.6637    0.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6402   -2.8383    0.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -2.6872   -3.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4511   -3.3553   -2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -3.1835   -1.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669   -1.7760   -2.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773   -2.3291   -0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664   -1.2442   -2.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5905    0.1733   -1.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9259   -0.3669   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.1562   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3518    1.8149   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176    3.9007    0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8865    2.5888   -0.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    3.6138   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    2.5960    2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3006    5.5223   -1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    5.5703   -2.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    3.8732   -2.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3357   -1.8826   -1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5285   -2.0022    2.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1226   -0.5627    1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -2.7315    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -1.1310    3.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616   -1.5617    2.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
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 19 20  1  0
 20 21  1  0
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 23 24  1  0
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 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 23 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 34  5  1  0
 19 14  1  0
 31 26  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  1
  4 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  6
  6 46  1  0
  9 47  1  6
 10 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 15 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 20 56  1  0
 23 57  1  6
 24 58  1  6
 25 59  1  0
 27 60  1  0
 28 61  1  0
 29 62  1  0
 30 63  1  0
 31 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂N₄O₅

Average Mass

480.5650 Da

Monoisotopic Mass

480.23727 Da

IUPAC Name

(3R,6R,9R)-6-[(2S)-butan-2-yl]-3-[(S)-hydroxy(phenyl)methyl]-4,9-dimethyl-2,3,4,5,6,7,8,9,10,11-decahydro-1H-1,4,7,10-benzotetrazacyclotridecine-2,5,8,11-tetrone

Traditional Name

(3R,6R,9R)-6-[(2S)-butan-2-yl]-3-[(S)-hydroxy(phenyl)methyl]-4,9-dimethyl-1,3,6,7,9,10-hexahydro-1,4,7,10-benzotetrazacyclotridecine-2,5,8,11-tetrone

CAS Registry Number

Not Available

SMILES

CCC(C)[C@H]1NC(=O)[C@@H](C)NC(=O)C2=CC=CC=C2NC(=O)[C@@H]([C@@H](O)C2=CC=CC=C2)N(C)C1=O

InChI Identifier

InChI=1S/C26H32N4O5/c1-5-15(2)20-26(35)30(4)21(22(31)17-11-7-6-8-12-17)25(34)28-19-14-10-9-13-18(19)24(33)27-16(3)23(32)29-20/h6-16,20-22,31H,5H2,1-4H3,(H,27,33)(H,28,34)(H,29,32)/t15?,16-,20-,21-,22+/m1/s1

InChI Key

AQBNNSWAQPPMPF-QZPRSPPASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus	NPAtlas	23806112

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Vinylogous amide
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.7	ALOGPS
logP	2.43	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.75 m³·mol⁻¹	ChemAxon
Polarizability	50.36 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

NPAtlas ID

NPA001366

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30770984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71726177

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He F, Bao J, Zhang XY, Tu ZC, Shi YM, Qi SH: Asperterrestide A, a cytotoxic cyclic tetrapeptide from the marine-derived fungus Aspergillus terreus SCSGAF0162. J Nat Prod. 2013 Jun 28;76(6):1182-6. doi: 10.1021/np300897v. Epub 2013 Jun 12. [PubMed:23806112 ]
Ohsawa K, Sugai M, Zhang L, Masuda Y, Yoshida M, Doi T: Total Synthesis and Structural Revision of Cyclotetrapeptide Asperterrestide A. J Org Chem. 2019 Jun 7;84(11):6765-6779. doi: 10.1021/acs.joc.9b00526. Epub 2019 May 22. [PubMed:31070032 ]
Cheung RC, Wong JH, Pan WL, Chan YS, Yin CM, Dan XL, Wang HX, Fang EF, Lam SK, Ngai PH, Xia LX, Liu F, Ye XY, Zhang GQ, Liu QH, Sha O, Lin P, Ki C, Bekhit AA, Bekhit Ael-D, Wan DC, Ye XJ, Xia J, Ng TB: Antifungal and antiviral products of marine organisms. Appl Microbiol Biotechnol. 2014 Apr;98(8):3475-94. doi: 10.1007/s00253-014-5575-0. Epub 2014 Feb 23. [PubMed:24562325 ]

Showing NP-Card for Asperterrestide A (NP0011890)

MOL for NP0011890 (Asperterrestide A)

3D MOL for NP0011890 (Asperterrestide A)

3D SDF for NP0011890 (Asperterrestide A)

3D-SDF for NP0011890 (Asperterrestide A)

PDB for NP0011890 (Asperterrestide A)

3D PDB for NP0011890 (Asperterrestide A)

SMILES for NP0011890 (Asperterrestide A)

INCHI for NP0011890 (Asperterrestide A)

Structure for NP0011890 (Asperterrestide A)

3D Structure for NP0011890 (Asperterrestide A)