NP-MRD: Showing NP-Card for Chromopyrrolic acid (NP0070062)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 15:20:09 UTC

Updated at

2022-04-28 15:20:09 UTC

NP-MRD ID

NP0070062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chromopyrrolic acid

Description

3,4-DI-1H-INDOL-3-YL-1H-PYRROLE-2,5-DICARBOXYLIC ACID, also known as 3,4-di(indol-3-yl)pyrrole-2,5-dicarboxylic acid, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Chromopyrrolic acid is found in Chromobacterium violaceum, Chromobacterium violaceum JCM1249 (ATCC12472) and Lycogala epidendrum. Chromopyrrolic acid was first documented in 2005 (PMID: 16313168). 3,4-DI-1H-INDOL-3-YL-1H-PYRROLE-2,5-DICARBOXYLIC ACID is a weakly acidic compound (based on its pKa) (PMID: 16874749) (PMID: 16967980) (PMID: 18481854) (PMID: 19246195).

Structure

MOL 3D MOL SDF PDB SMILES InChI

CRR
  Mrv0541 02241213312D          

 29 33  0  0  0  0            999 V2000
   -1.7057    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    0.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0111   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057   -1.2624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    2.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    1.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    1.3824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534    0.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534    1.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -0.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -2.0720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -1.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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  2  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 29  2  0  0  0  0
 22 23  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    3.0500    1.9472    1.7682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252    2.8524    1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    4.1499    1.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671    2.5605    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0291    3.4355    0.4662 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    2.7749   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    3.4295   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    2.7252   -1.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3215    4.7878   -0.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    1.4230   -0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761    0.3746   -0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    0.2390   -2.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6440   -0.8730   -2.2375 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987   -1.4705   -1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -2.6302   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437   -3.0595    0.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -2.2954    1.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977   -1.1346    1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -0.7213   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675    1.2994    0.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476    0.0792    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766   -0.4419    1.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057   -1.5803    1.6444 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585   -1.8118    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2040   -2.8166   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.7690   -1.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351   -1.7594   -2.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -0.7679   -1.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.7784   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    4.7457    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1044    4.4692    0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    5.4330   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939    0.9186   -2.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1093   -1.2644   -3.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8988   -3.2669   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464   -3.9812    1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -2.6348    2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -0.5138    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931   -0.0046    2.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7843   -2.1762    2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -3.6331    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953   -3.5730   -2.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266   -1.7401   -3.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.0534   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 20 10  1  0
 10  6  2  0
  6  5  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
  5  4  1  0
 19 11  1  0
 29 21  1  0
 15 14  1  0
 29 24  1  0
  3 30  1  0
 22 39  1  0
 23 40  1  0
 25 41  1  0
 26 42  1  0
 27 43  1  0
 28 44  1  0
  5 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 18 38  1  0
 17 37  1  0
 16 36  1  0
 15 35  1  0
M  END

CRR
  Mrv0541 02241213312D          

 29 33  0  0  0  0            999 V2000
   -1.7057    0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0412    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8617    0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    0.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0111   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057   -1.2624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -1.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536    1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    2.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    1.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    1.3824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534    0.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534    1.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -0.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850   -2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -1.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -2.0720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -1.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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  2  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 29  2  0  0  0  0
 22 23  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(C2=CNC3=CC=CC=C23)C(=C(N1)C(O)=O)C1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H15N3O4/c26-21(27)19-17(13-9-23-15-7-3-1-5-11(13)15)18(20(25-19)22(28)29)14-10-24-16-8-4-2-6-12(14)16/h1-10,23-25H,(H,26,27)(H,28,29)

> <INCHI_KEY>
FZDVNXHYGMEEDT-UHFFFAOYSA-N

> <FORMULA>
C22H15N3O4

> <MOLECULAR_WEIGHT>
385.3722

> <EXACT_MASS>
385.106255983

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57711863839528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-bis(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.7002727019999995

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.901886470672916

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2092218330216133

> <JCHEM_POLAR_SURFACE_AREA>
121.97

> <JCHEM_REFRACTIVITY>
107.5296

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lycogalic acid A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: CRR                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.184   0.135   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.810   1.542   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.342   1.703   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.247   0.457   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.621  -0.950   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.089  -1.111   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.184  -2.356   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.719  -1.881   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.719  -0.341   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.473   0.565   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.473   2.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.719   3.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.558   4.541   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.126   2.383   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       0.991   2.580   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.896   1.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.436   1.335   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.206   0.001   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.206   2.668   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.991   0.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.467  -1.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.932  -1.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.265  -1.082   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.599  -1.852   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.599  -3.392   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.265  -4.162   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.932  -3.392   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       1.467  -3.868   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       0.562  -2.622   0.000  0.00  0.00           C+0
CONECT    1    6    2    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15   20   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   10   16   21                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   22   26   28                                                  
CONECT   28   27   29                                                       
CONECT   29   21   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
3,4-Di(indol-3-yl)pyrrole-2,5-dicarboxylic acid	ChEBI
3,4-Di(indol-3-yl)pyrrole-2,5-dicarboxylate	Generator
3,4-DI-1H-indol-3-yl-1H-pyrrole-2,5-dicarboxylate	Generator
LYCOGARIC ACID a	ChEMBL
LYCOGARate a	Generator
Chromopyrrolic acid	MeSH
Chromopyrrolate	Generator

Chemical Formula

C₂₂H₁₅N₃O₄

Average Mass

385.3722 Da

Monoisotopic Mass

385.10626 Da

IUPAC Name

3,4-bis(1H-indol-3-yl)-1H-pyrrole-2,5-dicarboxylic acid

Traditional Name

lycogalic acid A

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(C2=CNC3=CC=CC=C23)C(=C(N1)C(O)=O)C1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C22H15N3O4/c26-21(27)19-17(13-9-23-15-7-3-1-5-11(13)15)18(20(25-19)22(28)29)14-10-24-16-8-4-2-6-12(14)16/h1-10,23-25H,(H,26,27)(H,28,29)

InChI Key

FZDVNXHYGMEEDT-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chromobacterium violaceum	LOTUS Database	35616633
Chromobacterium violaceum JCM1249 (ATCC12472)	Bacteria	KNApSAcK
Lycogala epidendrum	Amoebozoa	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Pyrrole-2-carboxylic acid
Pyrrole-2-carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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	3.9	ALOGPS
logP	3.7	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	121.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.53 m³·mol⁻¹	ChemAxon
Polarizability	38.58 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

Not Available

DrugBank ID

DB07588

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-11786

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11326613

PDB ID

Not Available

ChEBI ID

41625

Good Scents ID

Not Available

References

General References

Howard-Jones AR, Walsh CT: Enzymatic generation of the chromopyrrolic acid scaffold of rebeccamycin by the tandem action of RebO and RebD. Biochemistry. 2005 Dec 6;44(48):15652-63. doi: 10.1021/bi051706e. [PubMed:16313168 ]
Sanchez C, Brana AF, Mendez C, Salas JA: Reevaluation of the violacein biosynthetic pathway and its relationship to indolocarbazole biosynthesis. Chembiochem. 2006 Aug;7(8):1231-40. doi: 10.1002/cbic.200600029. [PubMed:16874749 ]
Howard-Jones AR, Walsh CT: Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid. J Am Chem Soc. 2006 Sep 20;128(37):12289-98. doi: 10.1021/ja063898m. [PubMed:16967980 ]
Wang Y, Hirao H, Chen H, Onaka H, Nagano S, Shaik S: Electron transfer activation of chromopyrrolic acid by cytochrome p450 en route to the formation of an antitumor indolocarbazole derivative: theory supports experiment. J Am Chem Soc. 2008 Jun 11;130(23):7170-1. doi: 10.1021/ja711426y. Epub 2008 May 16. [PubMed:18481854 ]
Chae CS, Park JS, Chung SC, Kim TI, Lee SH, Yoon KM, Shin J, Oh KB: Production of chromopyrrolic acid by coexpression of inkOD in a heterologous host Streptomyces albus. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1581-3. doi: 10.1016/j.bmcl.2009.02.026. Epub 2009 Feb 11. [PubMed:19246195 ]

Showing NP-Card for Chromopyrrolic acid (NP0070062)

MOL for NP0070062 (Chromopyrrolic acid)

3D MOL for NP0070062 (Chromopyrrolic acid)

3D SDF for NP0070062 (Chromopyrrolic acid)

3D-SDF for NP0070062 (Chromopyrrolic acid)

PDB for NP0070062 (Chromopyrrolic acid)

3D PDB for NP0070062 (Chromopyrrolic acid)

SMILES for NP0070062 (Chromopyrrolic acid)

INCHI for NP0070062 (Chromopyrrolic acid)

Structure for NP0070062 (Chromopyrrolic acid)

3D Structure for NP0070062 (Chromopyrrolic acid)