NP-MRD: Showing NP-Card for 4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole (NP0247744)

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Record Information

Version

2.0

Created at

2022-09-07 09:42:26 UTC

Updated at

2022-09-07 09:42:26 UTC

NP-MRD ID

NP0247744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole

Description

Prodigiosin belongs to the class of organic compounds known as dipyrrins. Dipyrrins are compounds containing two pyrrole rings fused via a methine (-C=) group. Prodigiosin 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. 4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole is found in Pseudoalteromonas rubra. 4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole was first documented in 2022 (PMID: 36063739). Based on a literature review a significant number of articles have been published on prodigiosin (PMID: 36048389) (PMID: 36030493) (PMID: 35992721) (PMID: 35972277) (PMID: 35956931) (PMID: 35944459).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -6.1672    1.8387    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5057    0.5625    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8340    0.3887   -1.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3277    0.3911   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009   -0.7007   -0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -0.5972   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5606    0.3062   -0.8265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774    0.0416   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758    0.6999   -0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2402    0.3433   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337    1.2517   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3797    0.6258   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734    1.2657    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9579    2.6042    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877    2.7511    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8113    1.4873    0.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105    0.6221    0.6117 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.7237   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7815   -0.9176   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328   -2.1375   -0.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -3.3422   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1556   -1.0732    0.3296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789   -1.4584    0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522   -2.6053    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9007    1.5822    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3789    2.4362    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0532    2.5294    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3571   -0.3348    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6136    0.5917   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1370   -0.5925   -1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2065    1.1598   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894    1.3591   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8664    0.3090   -2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518   -0.5506    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199   -1.7174   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    1.0872   -1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7175    1.5518   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002    2.2713   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172    3.3706    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8154    3.6952    0.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496    1.2447    1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885   -0.4239    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -1.5158    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -3.6395   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920   -3.2640    0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375   -4.1963   -0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638   -2.1380    2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6399   -3.1792    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9857   -3.2603    1.6044 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 19 18  1  0
 18 12  2  0
 12 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 23  6  1  0
 11 10  1  0
 17 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 18 43  1  0
 11 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1652309072211422D          

 24 26  0  0  0  0            999 V2000
   -4.5184   -5.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8039   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -5.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6605   -5.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460   -4.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1923   -4.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3597   -4.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802   -4.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102   -2.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776   -2.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0776   -1.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102   -1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901   -0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -1.2020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7450   -2.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -4.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395   -5.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0528   -3.6482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8598   -3.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 13 17  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 10 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=C\C(=C\C2=C(OC)C=C(N2)C2=CC=CN2)N=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12-

> <INCHI_KEY>
SZXDNGVQRDTJSD-VBKFSLOCSA-N

> <FORMULA>
C20H25N3O

> <MOLECULAR_WEIGHT>
323.44

> <EXACT_MASS>
323.199762437

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.387139962146534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-5-{[(2Z)-5-methyl-4-pentyl-2H-pyrrol-2-ylidene]methyl}-1H,1'H-2,2'-bipyrrole

> <JCHEM_LOGP>
4.129846932333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.954760985961006

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.557181800762201

> <JCHEM_PKA_STRONGEST_BASIC>
6.62240046046442

> <JCHEM_POLAR_SURFACE_AREA>
53.17

> <JCHEM_REFRACTIVITY>
101.025

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-5-{[(2Z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1H,1'H-2,2'-bipyrrole

> <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      -8.434  -9.432   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.101  -8.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.767  -9.432   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.433  -8.662   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.100  -9.432   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.766  -8.662   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.359  -9.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.671  -8.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.203  -8.305   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.108  -7.059   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.632  -5.594   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.878  -4.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.878  -3.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.632  -2.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.108  -0.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.648  -0.779   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       5.124  -2.244   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.124  -5.594   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.648  -7.059   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.553  -8.305   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.927  -9.711   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.099  -6.810   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.605  -7.130   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.749  -6.100   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   12   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    8   23                                                       
CONECT   23   22    6   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-2,2'-bipyrrole	ChEBI

Chemical Formula

C₂₀H₂₅N₃O

Average Mass

323.4400 Da

Monoisotopic Mass

323.19976 Da

IUPAC Name

4-methoxy-5-{[(2Z)-5-methyl-4-pentyl-2H-pyrrol-2-ylidene]methyl}-1H,1'H-2,2'-bipyrrole

Traditional Name

4-methoxy-5-{[(2Z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1H,1'H-2,2'-bipyrrole

CAS Registry Number

Not Available

SMILES

CCCCCC1=C\C(=C\C2=C(OC)C=C(N2)C2=CC=CN2)N=C1C

InChI Identifier

InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12-

InChI Key

SZXDNGVQRDTJSD-VBKFSLOCSA-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
Pseudoalteromonas rubra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipyrrins. Dipyrrins are compounds containing two pyrrole rings fused via a methine (-C=) group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Dipyrrins

Alternative Parents

Substituents

Dipyrrin
Alkyl aryl ether
Heteroaromatic compound
Ketimine
Ether
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Imine
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:82758 )
ring assembly (CHEBI:82758 )
tripyrrole (CHEBI:82758 )

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	4.13	ChemAxon
pKa (Strongest Acidic)	14.56	ChemAxon
pKa (Strongest Basic)	6.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.17 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	101.02 m³·mol⁻¹	ChemAxon
Polarizability	39.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017797

Chemspider ID

10612185

KEGG Compound ID

Not Available

BioCyc ID

CPD-16992

BiGG ID

Not Available

Wikipedia Link

Prodigiosin

METLIN ID

Not Available

PubChem Compound

153274519

PDB ID

Not Available

ChEBI ID

82758

Good Scents ID

rw1251331

References

General References

Zhu G, Tan W, Xie L, Ma C, Chen X, Zhang S, Wei Y: Mechanisms underlying the inhibitory effects of Cd(2+) on prodigiosin synthesis in Serratia marcescens KMR-3. J Inorg Biochem. 2022 Nov;236:111978. doi: 10.1016/j.jinorgbio.2022.111978. Epub 2022 Aug 27. [PubMed:36063739 ]
Alsharif KF, Albrakati A, Al Omairi NE, Almalki AS, Alsanie WF, Elmageed ZYA, Habotta OA, Lokman MS, Althagafi HA, Alghamdi AAA, Moneim AEA, Alyami H, Belal SKM, Alnefaie G, Alamri AS, Albezrah NKA, Kassab RB, Albarakati AJA, Hassan KE, Agil A: Therapeutic antischizophrenic activity of prodigiosin and selenium co-supplementation against amphetamine hydrochloride-induced behavioural changes and oxidative, inflammatory, and apoptotic challenges in rats. Environ Sci Pollut Res Int. 2023 Jan;30(3):7987-8001. doi: 10.1007/s11356-022-22409-x. Epub 2022 Sep 1. [PubMed:36048389 ]
Saleh N, Mahmoud HE, Eltaher H, Helmy M, El-Khordagui L, Hussein AA: Prodigiosin-Functionalized Probiotic Ghosts as a Bioinspired Combination Against Colorectal Cancer Cells. Probiotics Antimicrob Proteins. 2023 Oct;15(5):1271-1286. doi: 10.1007/s12602-022-09980-y. Epub 2022 Aug 28. [PubMed:36030493 ]
Pan X, You J, Tang M, Zhang X, Xu M, Yang T, Rao Z: Improving prodigiosin production by transcription factor engineering and promoter engineering in Serratia marcescens. Front Microbiol. 2022 Aug 3;13:977337. doi: 10.3389/fmicb.2022.977337. eCollection 2022. [PubMed:35992721 ]
Yin L, Zhang PP, Wang W, Tang S, Deng SM, Jia AQ: 3-Phenylpropan-1-Amine Enhanced Susceptibility of Serratia marcescens to Ofloxacin by Occluding Quorum Sensing. Microbiol Spectr. 2022 Oct 26;10(5):e0182922. doi: 10.1128/spectrum.01829-22. Epub 2022 Aug 16. [PubMed:35972277 ]
Araujo RG, Zavala NR, Castillo-Zacarias C, Barocio ME, Hidalgo-Vazquez E, Parra-Arroyo L, Rodriguez-Hernandez JA, Martinez-Prado MA, Sosa-Hernandez JE, Martinez-Ruiz M, Chen WN, Barcelo D, Iqbal HMN, Parra-Saldivar R: Recent Advances in Prodigiosin as a Bioactive Compound in Nanocomposite Applications. Molecules. 2022 Aug 5;27(15):4982. doi: 10.3390/molecules27154982. [PubMed:35956931 ]
Abdel-Rafei MK, Thabet NM, Amin MM: Concerted regulation of OPG/RANKL/ NF‑kappaB/MMP-13 trajectories contribute to ameliorative capability of prodigiosin and/or low dose gamma-radiation against adjuvant- induced arthritis in rats. Int Immunopharmacol. 2022 Oct;111:109068. doi: 10.1016/j.intimp.2022.109068. Epub 2022 Aug 6. [PubMed:35944459 ]
Zhang B, Yang Y, Xie W, He W, Xie J, Liu W: Identifying Algicides of Enterobacter hormaechei F2 for Control of the Harmful Alga Microcystis aeruginosa. Int J Environ Res Public Health. 2022 Jun 21;19(13):7556. doi: 10.3390/ijerph19137556. [PubMed:35805215 ]
Paul T, Mondal A, Bandyopadhyay TK, Mahata N, Bhunia B: Downstream Process Development for Extraction of Prodigiosin: Statistical Optimization, Kinetics, and Biochemical Characterization. Appl Biochem Biotechnol. 2022 Nov;194(11):5403-5418. doi: 10.1007/s12010-022-04053-w. Epub 2022 Jul 2. [PubMed:35779175 ]
Lazic J, Skaro Bogojevic S, Vojnovic S, Aleksic I, Milivojevic D, Kretzschmar M, Gulder T, Petkovic M, Nikodinovic-Runic J: Synthesis, Anticancer Potential and Comprehensive Toxicity Studies of Novel Brominated Derivatives of Bacterial Biopigment Prodigiosin from Serratia marcescens ATCC 27117. Molecules. 2022 Jun 9;27(12):3729. doi: 10.3390/molecules27123729. [PubMed:35744855 ]
Islan GA, Rodenak-Kladniew B, Noacco N, Duran N, Castro GR: Prodigiosin: a promising biomolecule with many potential biomedical applications. Bioengineered. 2022 Jun;13(6):14227-14258. doi: 10.1080/21655979.2022.2084498. [PubMed:35734783 ]
Siwawannapong K, Nemeth AM, Melander RJ, Rong J, Davis JR, Taniguchi M, Carpenter ME, Lindsey JS, Melander C: Simple Dipyrrin Analogues of Prodigiosin for Use as Colistin Adjuvants. ChemMedChem. 2022 Aug 17;17(16):e202200286. doi: 10.1002/cmdc.202200286. Epub 2022 Jul 8. [PubMed:35704751 ]
Elkenawy NM, Karam HM, Aboul-Magd DS: Development of gamma irradiated SSD-embedded hydrogel dyed with prodigiosin as a smart wound dressing: Evaluation in a MDR infected burn rat model. Int J Biol Macromol. 2022 Jun 30;211:170-182. doi: 10.1016/j.ijbiomac.2022.05.063. Epub 2022 May 13. [PubMed:35569674 ]
Nguyen SLT, Nguyen TC, Do TT, Vu TL, Nguyen TT, Do TT, Nguyen THT, Le TH, Trinh DK, Nguyen TAT: Study on the Anticancer Activity of Prodigiosin from Variants of Serratia Marcescens QBN VTCC 910026. Biomed Res Int. 2022 Apr 25;2022:4053074. doi: 10.1155/2022/4053074. eCollection 2022. [PubMed:35509712 ]
Tunca Koyun M, Sirin S, Aslim B, Taner G, Nigdelioglu Dolanbay S: Characterization of prodigiosin pigment by Serratia marcescens and the evaluation of its bioactivities. Toxicol In Vitro. 2022 Aug;82:105368. doi: 10.1016/j.tiv.2022.105368. Epub 2022 Apr 25. [PubMed:35476923 ]
LOTUS database [Link]

Showing NP-Card for 4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole (NP0247744)

MOL for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

3D MOL for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

3D SDF for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

3D-SDF for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

PDB for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

3D PDB for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

SMILES for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

INCHI for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

Structure for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)

3D Structure for NP0247744 (4-methoxy-5-{[(2z)-5-methyl-4-pentylpyrrol-2-ylidene]methyl}-1h,1'h-2,2'-bipyrrole)