MiMeDB: Showing metabocard for 5,6-Dihydroxyindole-2-carboxylic acid (MMDBc0047923)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:15:42 UTC

Update Date

2024-04-30 20:32:39 UTC

Metabolite ID

MMDBc0047923

Metabolite Identification

Common Name

5,6-Dihydroxyindole-2-carboxylic acid

Description

5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309152017122D          

 14 15  0  0  0  0            999 V2000
   -2.4807    1.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -0.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524    0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669    1.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -0.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -0.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322    1.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -0.3090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548    1.1200    0.0000 O   0  0  0  0  0  0  0  0  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  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  9 10  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047923

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CC2=CC(O)=C(O)C=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)

> <INCHI_KEY>
YFTGOBNOJKXZJC-UHFFFAOYSA-N

> <FORMULA>
C9H7NO4

> <MOLECULAR_WEIGHT>
193.1562

> <EXACT_MASS>
193.037507717

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.17230678832179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.042461197333333

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.725907037742457

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.112577263473689

> <JCHEM_PKA_STRONGEST_BASIC>
-6.3311678836379786

> <JCHEM_POLAR_SURFACE_AREA>
93.55000000000001

> <JCHEM_REFRACTIVITY>
48.24

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dhica

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  O   UNK     0      -4.631   2.293   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.638  -0.760   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.658   1.527   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.992   2.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.326   1.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.326  -0.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.992  -0.783   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.658  -0.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.807  -0.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.712   0.757   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.807   2.003   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.252   0.757   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.022  -0.577   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.022   2.091   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    4    8   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    1                                                  
CONECT    6    5    7    2                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9   10    8                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

Synonyms

Value	Source
5,6-DHICA	ChEBI
5,6-Dihydroxy-2-indolecarboxylic acid	ChEBI
5,6-Dihydroxy-2-indolylcarboxylic acid	ChEBI
5,6-Dihydroxyindole-2-carboxylate	ChEBI
DHI2c	ChEBI
DHICA	ChEBI
5,6-Dihydroxy-2-indolecarboxylate	Generator
5,6-Dihydroxy-2-indolylcarboxylate	Generator
5,6-Dihydroxy-1H-indole-2-carboxylate	HMDB
5,6-Dihydroxy-1H-indole-2-carboxylic acid	HMDB
2-Carboxy-5,6-dihydroxyindole	HMDB
5,6-Dihydroxy-2-carboxyindole	HMDB
5,6-Dihydroxyindole-2-carboxylic acid	HMDB

Molecular Formula

C₉H₇NO₄

Average Mass

193.1562

Monoisotopic Mass

193.037507717

IUPAC Name

5,6-dihydroxy-1H-indole-2-carboxylic acid

Traditional Name

dhica

CAS Registry Number

4790-08-3

SMILES

OC(=O)C1=CC2=CC(O)=C(O)C=C2N1

InChI Identifier

InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)

InChI Key

YFTGOBNOJKXZJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Hydroxyindole
Indole
Pyrrole-2-carboxylic acid
Pyrrole-2-carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyindole (CHEBI:2003 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.31 g/L	ALOGPS
logP	1.11	ALOGPS
logP	1.04	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	5.11	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	93.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.24 m³·mol⁻¹	ChemAxon
Polarizability	18.17 Å³	ChemAxon
Number of Rings	2	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	splash10-00dj-0900000000-86e3bb7f8c4c5358f1ef	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00du-5329000000-6168733ed8a73f569928	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0900000000-4323f8e82f9ef2c149e8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-5180e19b4ff79f8ccbe8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-3900000000-523d85a810268dbe9cf7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-6d7269d6d89c3eae16f9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-0900000000-4d67dcdd279043d44620	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006t-1900000000-968f54cfbf806d2e2389	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-0900000000-7937a0f008a025981516	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-b0b74fab2c882d47700d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xs-2900000000-a0ec9715df089ba80b98	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-b8d69868735567e6ffd7	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0900000000-b28b84208bb53ec6a35b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-5900000000-f33eeedd7677021f68df	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Feces

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
MMDBp0191773	Macrophage migration inhibitory factor	Enzyme	P14174	Homo sapiens
MMDBp0191879	L-dopachrome tautomerase	Unknown	P40126	Homo sapiens
MMDBp0193432	5,6-dihydroxyindole-2-carboxylic acid oxidase	Unknown	P17643	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Eumelanin Biosynthesis

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000636	L-Dopachrome	5,6-Dihydroxyindole-2-carboxylic acid	Not Available	VMH	8148378
MMDBr0002296	5,6-Dihydroxyindole-2-carboxylic acid	Melanin	tyrosinase-related protein 1	VMH	9434945
MMDBr0004611	5,6-Dihydroxyindole-2-carboxylic acid	5,6-Indolequinone-2-Carboxylate	Not Available	VMH	11171088

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	Firmicutes	2	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001253

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022514

KNApSAcK ID

Not Available

Chemspider ID

106648

KEGG Compound ID

C04185

BioCyc ID

56-DIHYDROXYINDOLE-2-CARBOXYLATE

BiGG ID

1444022

Wikipedia Link

Not Available

METLIN ID

6110

PubChem Compound

119405

PDB ID

Not Available

ChEBI ID

2003

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Yamada K, Walsh N, Hara H, Jimbow K, Chen H, Ito S: Measurement of eumelanin precursor metabolites in the urine as a new marker for melanoma metastases. Arch Dermatol. 1992 Apr;128(4):491-4. [PubMed:1580656 ]
Hansson C: Some indolic compounds as markers of the melanocyte activity. Acta Derm Venereol Suppl (Stockh). 1988;138:1-60. [PubMed:3176811 ]

Showing metabocard for 5,6-Dihydroxyindole-2-carboxylic acid (MMDBc0047923)

MOL for #<Metabolite:0x00007fdb08c609b8>

3D MOL for #<Metabolite:0x00007fdb08c609b8>

3D SDF for #<Metabolite:0x00007fdb08c609b8>

3D-SDF for #<Metabolite:0x00007fdb08c609b8>

PDB for #<Metabolite:0x00007fdb08c609b8>

3D PDB for #<Metabolite:0x00007fdb08c609b8>

SMILES for #<Metabolite:0x00007fdb08c609b8>

INCHI for #<Metabolite:0x00007fdb08c609b8>

Structure for #<Metabolite:0x00007fdb08c609b8>

3D Structure for #<Metabolite:0x00007fdb08c609b8>