NP-MRD: Showing NP-Card for Meleagrine (NP0014209)

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Record Information

Version

1.0

Created at

2021-01-05 23:26:26 UTC

Updated at

2021-07-15 17:16:40 UTC

NP-MRD ID

NP0014209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Meleagrine

Provided By

NPAtlas

Description

Meleagrine 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. Meleagrine is found in Penicillium oxalicum and Penicillium sp.. It was first documented in 2010 (PMID: 21053938). Based on a literature review very few articles have been published on meleagrine (PMID: 26030999) (PMID: 27476202).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121133D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242121133D          

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   -3.8892   -1.8824    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735   -2.2085    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198   -3.2825    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016   -2.9380   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -1.5130   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -3.2572   -3.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959   -1.2251   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.9685    3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1408    0.6744    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8052    0.3570    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.3915    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4260    2.7637   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586    3.2257   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318    3.8273   -2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663    3.8335   -1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647    4.1462   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3255    2.3123   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    0.1301   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 23  6  1  0  0  0  0
 32 27  1  0  0  0  0
 32  6  1  0  0  0  0
 23 12  1  0  0  0  0
 19 15  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
  7 42  1  0  0  0  0
  9 43  1  0  0  0  0
 14 44  1  0  0  0  0
 16 45  1  0  0  0  0
 18 46  1  0  0  0  0
 19 47  1  0  0  0  0
 22 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 28 52  1  0  0  0  0
 29 53  1  0  0  0  0
 30 54  1  0  0  0  0
 31 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])[C@@]2(C3=C([H])C([H])=C([H])C([H])=C3N(OC([H])([H])[H])[C@@]22N([H])C(=O)\C(=C(\[H])C3=C([H])N=C([H])N3[H])N2C1=O)C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m1/s1

> <INCHI_KEY>
JTJJJLSLKZFEPJ-WSHSOXHMSA-N

> <FORMULA>
C23H23N5O4

> <MOLECULAR_WEIGHT>
433.468

> <EXACT_MASS>
433.175004241

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.217547495018984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S,14E)-11-hydroxy-14-[(1H-imidazol-5-yl)methylidene]-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0^{1,13}.0^{3,8}]hexadeca-3,5,7,10-tetraene-12,15-dione

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
1.6550549987312797

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.280895990832285

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.697266409250289

> <JCHEM_PKA_STRONGEST_BASIC>
6.501706274358381

> <JCHEM_POLAR_SURFACE_AREA>
110.78999999999999

> <JCHEM_REFRACTIVITY>
130.49990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,14E)-11-hydroxy-14-(3H-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0^{1,13}.0^{3,8}]hexadeca-3,5,7,10-tetraene-12,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -1.4143   -1.2288    2.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9705   -0.7763    1.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -1.4000    0.4798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0454   -2.1230    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268   -2.4881    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162   -0.4323   -0.6224 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2849   -1.1912   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -1.5395   -2.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596   -2.2617   -3.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1517   -1.1903   -1.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -1.4938   -2.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0708   -0.4376   -0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.2221    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680   -0.6397    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -0.4015    1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402   -0.5588    2.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.1377    3.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279    0.2820    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389    0.1179    1.2700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618    0.6017    1.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.0233    2.4528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462    0.8508    0.8918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175    0.2680   -0.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2471    1.3820   -1.3399 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496    1.8579   -2.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599    2.9430   -1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    1.7598   -1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    3.0014   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    3.1981   -1.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2584    2.1434   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    0.9130   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.6807   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772   -0.7376    3.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -2.1262    2.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033    0.0989    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4005   -1.8813   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277   -3.2410    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8892   -1.8824    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735   -2.2085    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198   -3.2825    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016   -2.9380   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -1.5130   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -3.2572   -3.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959   -1.2251   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.9685    3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1408    0.6744    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8052    0.3570    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.3915    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4260    2.7637   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586    3.2257   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318    3.8273   -2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663    3.8335   -1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647    4.1462   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3255    2.3123   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    0.1301   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  6  3  1  0
  6  7  1  6
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 23  6  1  0
 32 27  1  0
 32  6  1  0
 23 12  1  0
 19 15  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  9 43  1  0
 14 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  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      -1.414  -1.229   2.895  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.970  -0.776   1.789  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.782  -1.400   0.480  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.045  -2.123   0.082  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.727  -2.488   0.609  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.416  -0.432  -0.622  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.285  -1.191  -1.891  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.149  -1.540  -2.465  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.160  -2.262  -3.663  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.152  -1.190  -1.892  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.259  -1.494  -2.383  0.00  0.00           O+0
HETATM   12  N   UNK     0       1.071  -0.438  -0.665  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.018  -0.222   0.372  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.268  -0.640   0.437  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.200  -0.402   1.518  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.140  -0.559   2.864  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.321  -0.138   3.388  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.128   0.282   2.402  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.439   0.118   1.270  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.362   0.602   1.363  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.878   1.023   2.453  0.00  0.00           O+0
HETATM   22  N   UNK     0       0.046   0.851   0.892  0.00  0.00           N+0
HETATM   23  C   UNK     0      -0.118   0.268  -0.374  0.00  0.00           C+0
HETATM   24  N   UNK     0      -0.247   1.382  -1.340  0.00  0.00           N+0
HETATM   25  O   UNK     0       0.750   1.858  -2.083  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.360   2.943  -1.471  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.608   1.760  -1.252  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.154   3.001  -1.543  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.497   3.198  -1.383  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.258   2.143  -0.935  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.709   0.913  -0.648  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.362   0.681  -0.798  0.00  0.00           C+0
HETATM   33  H   UNK     0      -1.577  -0.738   3.853  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.769  -2.126   2.871  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.603   0.099   1.864  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.401  -1.881  -0.928  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.928  -3.241   0.145  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.889  -1.882   0.795  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.174  -2.208   1.129  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.220  -3.283   1.242  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.602  -2.938  -0.389  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.180  -1.513  -2.450  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.088  -3.257  -3.701  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.596  -1.225  -0.440  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.296  -0.969   3.399  0.00  0.00           H+0
HETATM   46  H   UNK     0       7.141   0.674   2.533  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.805   0.357   0.324  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.652   1.391   1.442  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.426   2.764  -1.251  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.859   3.226  -0.523  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.332   3.827  -2.153  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.566   3.833  -1.894  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.965   4.146  -1.596  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.325   2.312  -0.812  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.353   0.130  -0.297  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3   39   40   41                                             
CONECT    6    3    7   23   32                                             
CONECT    7    6    8   42                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   43                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   45                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   46                                                  
CONECT   19   18   15   47                                                  
CONECT   20   13   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   48                                                  
CONECT   23   22   24    6   12                                             
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   49   50   51                                             
CONECT   27   24   28   32                                                  
CONECT   28   27   29   52                                                  
CONECT   29   28   30   53                                                  
CONECT   30   29   31   54                                                  
CONECT   31   30   32   55                                                  
CONECT   32   31   27    6                                                  
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   22                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
   -1.4143   -1.2288    2.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9705   -0.7763    1.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -1.4000    0.4798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0454   -2.1230    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268   -2.4881    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162   -0.4323   -0.6224 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2849   -1.1912   -1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -1.5395   -2.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596   -2.2617   -3.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1517   -1.1903   -1.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588   -1.4938   -2.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0708   -0.4376   -0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -0.2221    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680   -0.6397    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -0.4015    1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1402   -0.5588    2.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -0.1377    3.3882 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1279    0.2820    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389    0.1179    1.2700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3618    0.6017    1.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    1.0233    2.4528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462    0.8508    0.8918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175    0.2680   -0.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2471    1.3820   -1.3399 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496    1.8579   -2.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599    2.9430   -1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    1.7598   -1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    3.0014   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    3.1981   -1.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2584    2.1434   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    0.9130   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3624    0.6807   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772   -0.7376    3.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -2.1262    2.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033    0.0989    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4005   -1.8813   -0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277   -3.2410    0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8892   -1.8824    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735   -2.2085    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198   -3.2825    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6016   -2.9380   -0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805   -1.5130   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -3.2572   -3.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959   -1.2251   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963   -0.9685    3.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1408    0.6744    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8052    0.3570    0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.3915    1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4260    2.7637   -1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586    3.2257   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318    3.8273   -2.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5663    3.8335   -1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9647    4.1462   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3255    2.3123   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3528    0.1301   -0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  6  3  1  0
  6  7  1  6
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 23 22  1  1
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 23  6  1  0
 32 27  1  0
 32  6  1  0
 23 12  1  0
 19 15  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  9 43  1  0
 14 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Meleagrin	ChEBI

Chemical Formula

C₂₃H₂₃N₅O₄

Average Mass

433.4680 Da

Monoisotopic Mass

433.17500 Da

IUPAC Name

(1R,9S,14E)-11-hydroxy-14-[(1H-imidazol-5-yl)methylidene]-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0^{1,13}.0^{3,8}]hexadeca-3,5,7,10-tetraene-12,15-dione

Traditional Name

(1R,9S,14E)-11-hydroxy-14-(3H-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0^{1,13}.0^{3,8}]hexadeca-3,5,7,10-tetraene-12,15-dione

CAS Registry Number

Not Available

SMILES

[H]\C(C1=CN=CN1)=C1/N2C(=O)C(O)=C[C@@]3(C4=CC=CC=C4N(OC)[C@]23N=C1O)C(C)(C)C=C

InChI Identifier

InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m1/s1

InChI Key

JTJJJLSLKZFEPJ-WSHSOXHMSA-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
Penicillium oxalicum	LOTUS Database	35616633
Penicillium sp.	NPAtlas	26030999

Species Where Detected

Species Name	Source	Reference
Penicillium chrysogenum	KNApSAcK Database	22123792
Penicillium chrysogenum DS54555	KNApSAcK Database	22123792
Penicillium meleagrinum	KNApSAcK Database	22123792
Penicillium roqueforti	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	1.97	ALOGPS
logP	1.66	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.7	ChemAxon
pKa (Strongest Basic)	6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.79 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.5 m³·mol⁻¹	ChemAxon
Polarizability	44.22 Å³	ChemAxon
Number of Rings	5	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

NPA010351

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024790

Chemspider ID

10405606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meleagrin

METLIN ID

Not Available

PubChem Compound

23259517

PDB ID

Not Available

ChEBI ID

70399

Good Scents ID

Not Available

References

General References

Pimenta EF, Vita-Marques AM, Tininis A, Seleghim MH, Sette LD, Veloso K, Ferreira AG, Williams DE, Patrick BO, Dalisay DS, Andersen RJ, Berlinck RG: Use of experimental design for the optimization of the production of new secondary metabolites by two Penicillium species. J Nat Prod. 2010 Nov 29;73(11):1821-32. doi: 10.1021/np100470h. Epub 2010 Nov 5. [PubMed:21053938 ]
Yunianto P, Rusman Y, Saepudin E, Suwarso WP, Sumaryono W: Alkaloid (Meleagrine and Chrysogine) from endophytic fungi (Penicillium sp.) of Annona squamosa L. Pak J Biol Sci. 2014 May;17(5):667-74. doi: 10.3923/pjbs.2014.667.674. [PubMed:26030999 ]
Kozlovskii AG, Antipova TV, Zhelifonova VP, Baskunov BP, Kochkina GA, Ozerskaya SM: [Exometabolites of the Fungal Isolates (Genus Penicillium, Section Chrysogena) from Low-Temperature Ecotopes]. Mikrobiologiia. 2016 Mar-Apr;85(2):145-53. [PubMed:27476202 ]

Showing NP-Card for Meleagrine (NP0014209)

MOL for NP0014209 (Meleagrine)

3D MOL for NP0014209 (Meleagrine)

3D SDF for NP0014209 (Meleagrine)

3D-SDF for NP0014209 (Meleagrine)

PDB for NP0014209 (Meleagrine)

3D PDB for NP0014209 (Meleagrine)

SMILES for NP0014209 (Meleagrine)

INCHI for NP0014209 (Meleagrine)

Structure for NP0014209 (Meleagrine)

3D Structure for NP0014209 (Meleagrine)