MiMeDB: Showing metabocard for Chromopyrrolic acid (MMDBc0005886)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:18:36 UTC

Update Date

2022-08-31 06:24:35 UTC

Metabolite ID

MMDBc0005886

Metabolite 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. 3,4-DI-1H-INDOL-3-YL-1H-PYRROLE-2,5-DICARBOXYLIC ACID is a weakly acidic compound (based on its pKa).

Structure

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

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>
MMDBc0005886

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₂H₁₅N₃O₄

Average Mass

385.3722

Monoisotopic Mass

385.106255983

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

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-1019000000-0e7db66d376619b2bf4d	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ku-0009000000-3e53f93b4345ce4b272e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0039000000-111fd60c691c3d2bce21	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9x-0192000000-0f99bcfe48bfae8efe74	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-f34d0155f970005e645c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001l-0019000000-f895769aa9b7d26c3fb8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1296000000-16d361e95748d8554ad5	2017-07-26	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016529	2-iminio-3-(indol-3-yl)propanoic acid	Chromopyrrolic acid	Dichlorochromopyrrolate synthase	Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1
Bacteria	Proteobacteria	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB07588

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Chromopyrrolic acid (MMDBc0005886)

MOL for #<Metabolite:0x00007fa4b28d05c8>

3D MOL for #<Metabolite:0x00007fa4b28d05c8>

3D SDF for #<Metabolite:0x00007fa4b28d05c8>

3D-SDF for #<Metabolite:0x00007fa4b28d05c8>

PDB for #<Metabolite:0x00007fa4b28d05c8>

3D PDB for #<Metabolite:0x00007fa4b28d05c8>

SMILES for #<Metabolite:0x00007fa4b28d05c8>

INCHI for #<Metabolite:0x00007fa4b28d05c8>

Structure for #<Metabolite:0x00007fa4b28d05c8>

3D Structure for #<Metabolite:0x00007fa4b28d05c8>