NP-MRD: Showing NP-Card for 3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one (NP0156207)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:22:52 UTC

Updated at

2022-09-02 13:22:52 UTC

NP-MRD ID

NP0156207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one

Description

Violacein belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one is found in Chromobacterium violaceum. 3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one was first documented in 2022 (PMID: 35624712). Based on a literature review a significant number of articles have been published on Violacein (PMID: 35884107) (PMID: 35956830) (PMID: 35910130) (PMID: 35907084) (PMID: 35876575) (PMID: 35875582).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215222D          

 26 30  0  0  0  0            999 V2000
    0.0992   -5.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529   -4.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583   -4.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5089   -2.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -2.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529   -3.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -2.8174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 14 23  1  0  0  0  0
 17 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    2.6765   -0.7665    3.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3376   -0.5347    2.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7373   -0.6596    2.0806 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093   -0.3118    0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -0.2829    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3223    0.1167   -1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1530    0.4753   -1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281    0.4446   -1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    0.0455    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981   -0.0646    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.2289    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -0.6720    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.0427    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1108   -0.7551    0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699   -2.1152    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -2.4872    0.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -1.3985   -0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6039   -1.2862   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0758   -0.0280   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2221    1.0502   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7422    2.2818   -1.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8640    0.9039   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3644   -0.3194   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    1.2274    0.1218 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8179    1.4166    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821    2.6178    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1448   -0.5637    0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869    0.1490   -1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2082    0.7895   -2.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065    0.7245   -1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4508   -1.7346    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574   -2.7698    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183   -3.4483    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2580   -2.1497   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1357    0.0510   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8041    2.6141   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2167    1.7462   -0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371    2.0111   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    3.4965    0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 11  2  0
 11 12  1  0
 12 13  2  0
 13 24  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 24 25  1  0
 23 14  1  0
  2 10  1  0
 23 17  1  0
  4  9  1  0
 26 39  1  0
 12 31  1  0
 24 38  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
 22 37  1  0
  8 30  1  0
  7 29  1  0
  6 28  1  0
  5 27  1  0
M  END


  Mrv1652309022215222D          

 26 30  0  0  0  0            999 V2000
    0.0992   -5.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -4.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529   -4.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6583   -4.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5089   -2.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -2.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3529   -3.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -2.8174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 14 23  1  0  0  0  0
 17 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156207

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(C=C(N1)C1=CNC2=CC=C(O)C=C12)C1=C2C=CC=CC2=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,23-25H

> <INCHI_KEY>
SHLJIZCPRXXHHZ-UHFFFAOYSA-N

> <FORMULA>
C20H13N3O3

> <MOLECULAR_WEIGHT>
343.342

> <EXACT_MASS>
343.095691291

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.98714720699519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]-2H-indol-2-one

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
2.670175085666666

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.196757382066096

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.668738346625931

> <JCHEM_PKA_STRONGEST_BASIC>
0.05497970975744537

> <JCHEM_POLAR_SURFACE_AREA>
101.47

> <JCHEM_REFRACTIVITY>
99.45630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       0.185  -9.380   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.061  -8.474   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.525  -8.950   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.431  -7.704   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.962  -7.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.589  -6.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.683  -4.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.152  -5.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.525  -6.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.185  -4.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.555  -5.259   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.126  -7.970   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   14   17                                                  
CONECT   24   13   25                                                       
CONECT   25   24   11   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
3-(1,2-Dihydro-5-(5-hydroxy-1H-indole-3-yl)-2-oxo-3H-pyrrol-3-ylidene)-1,3-dihydro-2H-indole-2-one	HMDB
(3E)-3-(1,2-Dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene)-1,3-dihydro-2H-indol-2-one	HMDB

Chemical Formula

C₂₀H₁₃N₃O₃

Average Mass

343.3420 Da

Monoisotopic Mass

343.09569 Da

IUPAC Name

3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]-2H-indol-2-one

Traditional Name

3-[2-hydroxy-5-(5-hydroxy-1H-indol-3-yl)-1H-pyrrol-3-yl]indol-2-one

CAS Registry Number

Not Available

SMILES

OC1=C(C=C(N1)C1=CNC2=CC=C(O)C=C12)C1=C2C=CC=CC2=NC1=O

InChI Identifier

InChI=1S/C20H13N3O3/c24-10-5-6-15-12(7-10)14(9-21-15)17-8-13(19(25)23-17)18-11-3-1-2-4-16(11)22-20(18)26/h1-9,21,23-25H

InChI Key

SHLJIZCPRXXHHZ-UHFFFAOYSA-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
Chromobacterium violaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
N-acylimine
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.81	ALOGPS
logP	2.67	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	0.055	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.46 m³·mol⁻¹	ChemAxon
Polarizability	35.99 Å³	ChemAxon
Number of Rings	5	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

HMDB0259831

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029223

Chemspider ID

78435916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Violacein

METLIN ID

Not Available

PubChem Compound

11053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cheng KC, Hsiao HC, Hou YC, Hsieh CW, Hsu HY, Chen HY, Lin SP: Improvement in Violacein Production by Utilizing Formic Acid to Induce Quorum Sensing in Chromobacterium violaceum. Antioxidants (Basel). 2022 Apr 26;11(5). pii: antiox11050849. doi: 10.3390/antiox11050849. [PubMed:35624712 ]
Awadelkareem AM, Al-Shammari E, Elkhalifa AO, Adnan M, Siddiqui AJ, Patel M, Khan MI, Mehmood K, Ashfaq F, Badraoui R, Ashraf SA: Biosynthesized Silver Nanoparticles from Eruca sativa Miller Leaf Extract Exhibits Antibacterial, Antioxidant, Anti-Quorum-Sensing, Antibiofilm, and Anti-Metastatic Activities. Antibiotics (Basel). 2022 Jun 25;11(7):853. doi: 10.3390/antibiotics11070853. [PubMed:35884107 ]
Li YL, Chu ZY, Liu GM, Yang SQ, Zeng H: The Derived Components of Gnaphalium hypoleucum DC. Reduce Quorum Sensing of Chromobacterium violaceum. Molecules. 2022 Jul 30;27(15):4881. doi: 10.3390/molecules27154881. [PubMed:35956830 ]
Kachhadia R, Kapadia C, Singh S, Gandhi K, Jajda H, Alfarraj S, Ansari MJ, Danish S, Datta R: Quorum Sensing Inhibitory and Quenching Activity of Bacillus cereus RC1 Extracts on Soft Rot-Causing Bacteria Lelliottia amnigena. ACS Omega. 2022 Jul 11;7(29):25291-25308. doi: 10.1021/acsomega.2c02202. eCollection 2022 Jul 26. [PubMed:35910130 ]
Alibi S, Selma WB, Mansour HB, Navas J: Activity of Essential Oils Against Multidrug-Resistant Salmonella enteritidis. Curr Microbiol. 2022 Jul 30;79(9):273. doi: 10.1007/s00284-022-02938-x. [PubMed:35907084 ]
Alves JA, Leal FC, Previato-Mello M, da Silva Neto JF: A Quorum Sensing-Regulated Type VI Secretion System Containing Multiple Nonredundant VgrG Proteins Is Required for Interbacterial Competition in Chromobacterium violaceum. Microbiol Spectr. 2022 Aug 31;10(4):e0157622. doi: 10.1128/spectrum.01576-22. Epub 2022 Jul 25. [PubMed:35876575 ]
Kumar V, Kashyap P, Kumar S, Thakur V, Kumar S, Singh D: Multiple Adaptive Strategies of Himalayan Iodobacter sp. PCH194 to High-Altitude Stresses. Front Microbiol. 2022 Jul 6;13:881873. doi: 10.3389/fmicb.2022.881873. eCollection 2022. [PubMed:35875582 ]
Rivero Berti I, Rodenak-Kladniew BE, Katz SF, Arrua EC, Alvarez VA, Duran N, Castro GR: Enzymatic Active Release of Violacein Present in Nanostructured Lipid Carrier by Lipase Encapsulated in 3D-Bioprinted Chitosan-Hydroxypropyl Methylcellulose Matrix With Anticancer Activity. Front Chem. 2022 Jul 7;10:914126. doi: 10.3389/fchem.2022.914126. eCollection 2022. [PubMed:35873038 ]
Faria AVS, Fonseca EMB, Fernandes-Oliveira PS, de Lima TI, Clerici SP, Justo GZ, Silveira LR, Duran N, Ferreira-Halder CV: Violacein switches off low molecular weight tyrosine phosphatase and rewires mitochondria in colorectal cancer cells. Bioorg Chem. 2022 Oct;127:106000. doi: 10.1016/j.bioorg.2022.106000. Epub 2022 Jul 8. [PubMed:35853296 ]
Doganci MA, Ay Sal F, Guler HI, Kati H, Ceylan E, Belduz AO, Bozdal G, Yayli N, Canakci S: Investigation of potential inhibitor properties of violacein against HIV-1 RT and CoV-2 Spike RBD:ACE-2. World J Microbiol Biotechnol. 2022 Jul 14;38(9):161. doi: 10.1007/s11274-022-03350-0. [PubMed:35834025 ]
Hui CY, Guo Y, Zhu DL, Li LM, Yi J, Zhang NX: Metabolic engineering of the violacein biosynthetic pathway toward a low-cost, minimal-equipment lead biosensor. Biosens Bioelectron. 2022 Oct 15;214:114531. doi: 10.1016/j.bios.2022.114531. Epub 2022 Jul 6. [PubMed:35810697 ]
Karuppiah V, Seralathan M: Quorum sensing inhibitory potential of vaccenic acid against Chromobacterium violaceum and methicillin-resistant Staphylococcus aureus. World J Microbiol Biotechnol. 2022 Jun 27;38(8):146. doi: 10.1007/s11274-022-03335-z. [PubMed:35759150 ]
Kanelli M, Saleh B, Webster TJ, Vouyiouka S, Topakas E: Co-Encapsulation of Violacein and Iron Oxide in Poly(lactic acid) Nanoparticles for Simultaneous Antibacterial and Anticancer Applications. J Biomed Nanotechnol. 2022 Mar 1;18(3):729-739. doi: 10.1166/jbn.2022.3305. [PubMed:35715912 ]
Duran N, Castro GR, Portela RWD, Favaro WJ, Duran M, Tasic L, Nakazato G: Violacein and its antifungal activity: comments and potentialities. Lett Appl Microbiol. 2022 Oct;75(4):796-803. doi: 10.1111/lam.13760. Epub 2022 Jun 22. [PubMed:35687081 ]
de Souza Oliveira PF, Faria AVS, Clerici SP, Akagi EM, Carvalho HF, Justo GZ, Duran N, Ferreira-Halder CV: Violacein negatively modulates the colorectal cancer survival and epithelial-mesenchymal transition. J Cell Biochem. 2022 Jul;123(7):1247-1258. doi: 10.1002/jcb.30295. Epub 2022 Jun 6. [PubMed:35661241 ]
Ulusoy S, B Akalin R, Cevikbas H, Berisha A, Oral A, Bosgelmez-Tinaz G: Zeolite 4A as a jammer of bacterial communication in Chromobacterium violaceum and Pseudomonas aeruginosa. Future Microbiol. 2022 Jul;17:861-871. doi: 10.2217/fmb-2021-0174. Epub 2022 Jun 6. [PubMed:35658574 ]
Pothoulakis G, Nguyen MTA, Andersen ES: Utilizing RNA origami scaffolds in Saccharomyces cerevisiae for dCas9-mediated transcriptional control. Nucleic Acids Res. 2022 Jul 8;50(12):7176-7187. doi: 10.1093/nar/gkac470. [PubMed:35648481 ]
Dahlem C, Chanda S, Hemmer J, Schymik HS, Kohlstedt M, Wittmann C, Kiemer AK: Characterization of Anti-Cancer Activities of Violacein: Actions on Tumor Cells and the Tumor Microenvironment. Front Oncol. 2022 May 11;12:872223. doi: 10.3389/fonc.2022.872223. eCollection 2022. [PubMed:35646663 ]
Chernogor L, Bakhvalova K, Belikova A, Belikov S: Isolation and Properties of the Bacterial Strain Janthinobacterium sp. SLB01. Microorganisms. 2022 May 23;10(5):1071. doi: 10.3390/microorganisms10051071. [PubMed:35630513 ]
Patel M, Siddiqui AJ, Ashraf SA, Surti M, Awadelkareem AM, Snoussi M, Hamadou WS, Bardakci F, Jamal A, Jahan S, Sachidanandan M, Adnan M: Lactiplantibacillus plantarum-Derived Biosurfactant Attenuates Quorum Sensing-Mediated Virulence and Biofilm Formation in Pseudomonas aeruginosa and Chromobacterium violaceum. Microorganisms. 2022 May 13;10(5):1026. doi: 10.3390/microorganisms10051026. [PubMed:35630468 ]
LOTUS database [Link]

Showing NP-Card for 3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one (NP0156207)

MOL for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

3D MOL for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

3D SDF for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

3D-SDF for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

PDB for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

3D PDB for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

SMILES for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

INCHI for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

Structure for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)

3D Structure for NP0156207 (3-[2-hydroxy-5-(5-hydroxy-1h-indol-3-yl)-1h-pyrrol-3-yl]indol-2-one)