NP-MRD: Showing NP-Card for 5,6-Dihydroxyindole-2-carboxylic acid (NP0086737)

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Record Information

Version

2.0

Created at

2022-05-11 16:29:35 UTC

Updated at

2022-05-11 16:29:35 UTC

NP-MRD ID

NP0086737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dihydroxyindole-2-carboxylic acid

Description

5,6-Dihydroxyindole-2-carboxylic acid, also known as DHICA, 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. A dihydroxyindole that is indole-2-carboxylic acid substituted by hydroxy groups at positions 5 and 6. 5,6-Dihydroxyindole-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 5,6-dihydroxyindole-2-carboxylic acid participates in a number of enzymatic reactions. In particular, 5,6-dihydroxyindole-2-carboxylic acid can be biosynthesized from L-dopachrome through its interaction with the enzyme L-dopachrome tautomerase. In addition, 5,6-dihydroxyindole-2-carboxylic acid can be converted into indole-5,6-quinone-2-carboxylate; which is catalyzed by the enzyme tyrosinase. 5,6-Dihydroxyindole-2-carboxylic acid is found in Mus musculus. 5,6-Dihydroxyindole-2-carboxylic acid was first documented in 1988 (PMID: 3176811). In humans, 5,6-dihydroxyindole-2-carboxylic acid is involved in eumelanin biosynthesis (PMID: 1580656) (PMID: 25450182).

Structure

MOL 3D MOL SDF 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>
NP0086737

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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

Chemical Formula

C₉H₇NO₄

Average Mass

193.1562 Da

Monoisotopic Mass

193.03751 Da

IUPAC Name

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

Traditional Name

dhica

CAS Registry Number

Not Available

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

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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

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	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

External Links

HMDB ID

HMDB0001253

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Hansson C: Some indolic compounds as markers of the melanocyte activity. Acta Derm Venereol Suppl (Stockh). 1988;138:1-60. [PubMed:3176811 ]
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 ]
Kishida R, Saputro AG, Kasai H: Mechanism of dopachrome tautomerization into 5,6-dihydroxyindole-2-carboxylic acid catalyzed by Cu(II) based on quantum chemical calculations. Biochim Biophys Acta. 2015 Feb;1850(2):281-6. doi: 10.1016/j.bbagen.2014.10.024. Epub 2014 Oct 28. [PubMed:25450182 ]

Showing NP-Card for 5,6-Dihydroxyindole-2-carboxylic acid (NP0086737)

MOL for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

3D MOL for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

3D SDF for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

3D-SDF for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

PDB for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

3D PDB for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

SMILES for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

INCHI for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

Structure for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)

3D Structure for NP0086737 (5,6-Dihydroxyindole-2-carboxylic acid)