NP-MRD: Showing NP-Card for (14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one (NP0251505)

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Record Information

Version

2.0

Created at

2022-09-07 14:43:19 UTC

Updated at

2022-09-07 14:43:19 UTC

NP-MRD ID

NP0251505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one

Description

Meleagrine belongs to the class of organic compounds known as pyridoindolones. These are pyridoindoles with a structure that contains an indole moiety bearing a ketone. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one is found in Penicillium meleagrinum. (14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one was first documented in 2014 (PMID: 26030999). Meleagrine is a very strong basic compound (based on its pKa) (PMID: 27476202).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306302022162D          

 32 36  0  0  0  0            999 V2000
   -1.2374    0.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386    1.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -0.3712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811   -0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786    2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    0.2475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    0.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8561   -0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199   -2.2686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749   -2.9286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811   -2.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0624    0.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    2.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.5362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010   -1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
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  9 30  1  0  0  0  0
 30 19  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
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   -1.1135   -2.5494    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829   -1.7642   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4524    0.2013   -1.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8192    1.0609   -2.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.6175   -2.6990 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0342    0.6175   -0.7492 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    0.2352    0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    0.1838   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -0.2194    0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237    0.3750    0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4344   -0.3226    1.4197 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6821   -1.3206    1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4932   -1.2398    1.3040 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.0397    1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -0.4028    2.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    0.1811    1.3942 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.5117    0.0696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8213    1.8318    0.0211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3304    2.9879   -0.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867    4.0094    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    1.5333    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787    2.3681    1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816    1.8771    1.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839    0.5606    1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6095   -0.2706    0.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    0.1874    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9153   -3.7066    0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8174   -2.2208   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4089    0.0745   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018    1.0910   -4.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481    0.4449   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    1.2448   -0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4338   -0.1288    1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9905   -2.0666    2.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241    0.1198    2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    3.7170    1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723    4.7509    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952    4.5450    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888    3.4164    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8595    2.5228    2.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266    0.1197    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8901   -1.2988    0.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 24  1  0
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 27 32  2  0
 32 31  1  0
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 32  6  1  0
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 23 22  1  1
  6  3  1  6
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  2  1  2  3
 23 24  1  0
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 23 12  1  0
 19 15  1  0
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  5 41  1  0
  2 35  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652306302022162D          

 32 36  0  0  0  0            999 V2000
   -1.2374    0.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4537    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386    1.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -0.3712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811    0.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6811   -0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786    2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662    3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    0.2475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    0.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8561   -0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199   -2.2686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749   -2.9286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0624    0.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    2.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -0.5362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010   -1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  6  8  2  0  0  0  0
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  2  9  1  0  0  0  0
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  2 10  1  0  0  0  0
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 15 20  1  0  0  0  0
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 22 27  2  0  0  0  0
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 30 19  1  0  0  0  0
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 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C2=C(C=CC=C2)C2(C=C(O)C(=O)N3\C(=C\C4=CNC=N4)C(=O)NC123)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+

> <INCHI_KEY>
JTJJJLSLKZFEPJ-LICLKQGHSA-N

> <FORMULA>
C23H23N5O4

> <MOLECULAR_WEIGHT>
433.468

> <EXACT_MASS>
433.175004241

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.301879414836435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(14E)-11-hydroxy-14-[(1H-imidazol-4-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(8),4,6,10-tetraene-12,15-dione

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.0245552295891316

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.296643175135396

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.672344411278182

> <JCHEM_PKA_STRONGEST_BASIC>
6.0228964668650224

> <JCHEM_POLAR_SURFACE_AREA>
110.79

> <JCHEM_REFRACTIVITY>
130.17529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14E)-11-hydroxy-14-(1H-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(8),4,6,10-tetraene-12,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-20         0                                  
HETATM    1  C   UNK     0      -2.310   1.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.847   1.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310  -0.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.619   2.156   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.232  -0.693   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.696  -1.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.005   1.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.005  -0.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.617   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.616   4.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.157   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.387   4.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.617   5.698   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.540   0.462   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.310   1.848   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540   3.157   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   3.157   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.770  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.002  -1.001   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.924  -3.465   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.619  -3.234   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.465  -1.617   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.464  -4.235   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.080  -5.698   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       4.620  -5.467   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       5.005  -4.004   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.850   1.848   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.310   4.466   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0      -0.385  -1.001   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      -2.002  -2.079   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.548  -2.079   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    9   10   18                                             
CONECT    3    1    5    6                                                  
CONECT    4    1    7                                                       
CONECT    5    3    9   31                                                  
CONECT    6    3    8                                                       
CONECT    7    4    8                                                       
CONECT    8    6    7                                                       
CONECT    9    2    5   15   30                                             
CONECT   10    2   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15    9   16   20                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   29                                                  
CONECT   18   17    2                                                       
CONECT   19   20   21   30                                                  
CONECT   20   19   15   23                                                  
CONECT   21   19                                                            
CONECT   22   23   24   27                                                  
CONECT   23   22   20                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30    9   19                                                       
CONECT   31    5   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃N₅O₄

Average Mass

433.4680 Da

Monoisotopic Mass

433.17500 Da

IUPAC Name

(14E)-11-hydroxy-14-[(1H-imidazol-4-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(8),4,6,10-tetraene-12,15-dione

Traditional Name

(14E)-11-hydroxy-14-(1H-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(8),4,6,10-tetraene-12,15-dione

CAS Registry Number

Not Available

SMILES

CON1C2=C(C=CC=C2)C2(C=C(O)C(=O)N3\C(=C\C4=CNC=N4)C(=O)NC123)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+

InChI Key

JTJJJLSLKZFEPJ-LICLKQGHSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium meleagrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridoindolones. These are pyridoindoles with a structure that contains an indole moiety bearing a ketone. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Pyridoindolones

Alternative Parents

Substituents

Pyridoindolone
Alpha-carboline
Alpha-amino acid or derivatives
Imidazopyridine
Indole
1-hydroxylamino, 4-unsubstituted benzenoid
1-hydroxylamino, 2-unsubstituted benzenoid
Imidazolidinone
Benzenoid
Pyridine
Azole
Imidazole
Imidazolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Carboxamide group
Secondary carboxylic acid amide
Lactam
Ortho amide
Orthocarboxylic acid derivative
N-organohydroxylamine
Azacycle
Enol
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
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	2.1	ALOGPS
logP	2.02	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	6.02	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	130.18 m³·mol⁻¹	ChemAxon
Polarizability	44.3 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16479132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17985147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
LOTUS database [Link]

Showing NP-Card for (14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one (NP0251505)

MOL for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

3D MOL for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

3D SDF for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

3D-SDF for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

PDB for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

3D PDB for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

SMILES for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

INCHI for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

Structure for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)

3D Structure for NP0251505 ((14e)-11,15-dihydroxy-14-(3h-imidazol-4-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0¹,¹³.0³,⁸]hexadeca-3,5,7,10,15-pentaen-12-one)