NP-MRD: Showing NP-Card for (1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0252679)

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Record Information

Version

2.0

Created at

2022-09-07 16:16:03 UTC

Updated at

2022-09-07 16:16:03 UTC

NP-MRD ID

NP0252679

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

Verrucofortine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Penicillium verrucosum. (1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one was first documented in 2007 (PMID: 18095438). Based on a literature review a small amount of articles have been published on Verrucofortine (PMID: 26243556) (PMID: 25109845).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218162D          

 30 33  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -1.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
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  8 19  1  1  0  0  0
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 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
  6 30  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -2.2571   -1.5097   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0777   -1.6406   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7107    0.3954   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622    0.3845   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040    0.4783   -2.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2682    0.4169   -0.4629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1612    0.6779   -0.5880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3668    1.9758    0.0475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    3.0826   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    4.3825    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5340    2.9608   -0.8309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792    1.8131    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4328    2.8212    1.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5646    2.4782    1.9511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8196    1.1450    2.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9997    0.1403    1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8480    0.4760    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2498   -2.0788    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9326   -1.5520   -1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144   -0.1165   -2.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3602   -1.5312   -2.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0384   -2.1927   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6581    0.9202   -2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7698    0.1179   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3835    1.0135   -0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482    0.6429   -1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277    4.9460    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9469    4.2614    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810    4.9901    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949    3.8567    1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7122    0.8398    2.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309072218162D          

 30 33  0  0  1  0            999 V2000
    0.7890    2.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4437    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6630    0.0391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -1.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  6  7  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0252679

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@@H]2C[C@@]3([C@@H](N(C(C)=O)C4=CC=CC=C34)N2C1=O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)/t17-,19-,22-,24+/m0/s1

> <INCHI_KEY>
BMRZKNPRSPWNNW-UNBWHIKDSA-N

> <FORMULA>
C24H31N3O3

> <MOLECULAR_WEIGHT>
409.53

> <EXACT_MASS>
409.23654187

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.151374668341646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,7S,9R)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_LOGP>
3.578464638333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.188771900682642

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.626016535670605

> <JCHEM_PKA_STRONGEST_BASIC>
1.424903979596955

> <JCHEM_POLAR_SURFACE_AREA>
73.21000000000001

> <JCHEM_REFRACTIVITY>
114.46119999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7S,9R)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.473   4.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.738  -0.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.028   0.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.903  -1.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.039  -2.508   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.812  -3.438   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.458  -3.106   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   20   30                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25    6                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₁N₃O₃

Average Mass

409.5300 Da

Monoisotopic Mass

409.23654 Da

IUPAC Name

(1R,4S,7S,9R)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

Traditional Name

(1R,4S,7S,9R)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@@H]2C[C@@]3([C@@H](N(C(C)=O)C4=CC=CC=C34)N2C1=O)C(C)(C)C=C

InChI Identifier

InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)/t17-,19-,22-,24+/m0/s1

InChI Key

BMRZKNPRSPWNNW-UNBWHIKDSA-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 verrucosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. 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

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Acetamide
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	3.58	ChemAxon
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	1.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.46 m³·mol⁻¹	ChemAxon
Polarizability	45.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

106464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M: Penicyrones A and B, an epimeric pair of alpha-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. [PubMed:26243556 ]
Santini A, Mikusova P, Sulyok M, Krska R, Labuda R, Srobarova A: Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile. Mycotoxin Res. 2014 Nov;30(4):213-20. doi: 10.1007/s12550-014-0205-3. Epub 2014 Aug 12. [PubMed:25109845 ]
Nunez F, Westphal CD, Bermudez E, Asensio MA: Production of secondary metabolites by some terverticillate penicillia on carbohydrate-rich and meat substrates. J Food Prot. 2007 Dec;70(12):2829-36. doi: 10.4315/0362-028x-70.12.2829. [PubMed:18095438 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0252679)

MOL for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0252679 ((1r,4s,7s,9r)-16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)