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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:33 UTC

HMDB ID

HMDB0001253

Secondary Accession Numbers

HMDB01253

Metabolite 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. In humans, 5,6-dihydroxyindole-2-carboxylic acid is involved in eumelanin biosynthesis.

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>
HMDB0001253

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

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 Molecular Weight

193.1562

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0001253)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Tyrosine Metabolism (HMDB: HMDB0001253)
Eumelanin Biosynthesis (PathBank: SMP0121124)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0001253)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.799	31661259
DarkChem	[M-H]-	141.992	31661259
AllCCS	[M+H]+	140.866	32859911
AllCCS	[M-H]-	137.527	32859911
DeepCCS	[M+H]+	134.881	30932474
DeepCCS	[M-H]-	132.472	30932474
DeepCCS	[M-2H]-	168.027	30932474
DeepCCS	[M+Na]+	143.565	30932474
AllCCS	[M+H]+	140.9	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	146.1	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	137.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.91 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0485 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.44 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	84.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1691.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	368.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	60.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	447.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	283.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	655.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	256.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1126.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	718.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	234.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	324.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydroxyindole-2-carboxylic acid	OC(=O)C1=CC2=CC(O)=C(O)C=C2N1	3573.5	Standard polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid	OC(=O)C1=CC2=CC(O)=C(O)C=C2N1	2135.1	Standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid	OC(=O)C1=CC2=CC(O)=C(O)C=C2N1	2152.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2[NH]1	2342.6	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C(C(=O)O)=C2	2280.4	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C(C(=O)O)[NH]2)C=C1O	2286.2	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #4	C[Si](C)(C)N1C(C(=O)O)=CC2=CC(O)=C(O)C=C21	2323.5	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O)C=C2[NH]1	2281.4	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C)C=C2[NH]1	2292.5	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C	2337.1	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C(C(=O)O)=C2	2283.2	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)C(C(=O)O)=C2	2324.7	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C=C1O)C=C(C(=O)O)N2[Si](C)(C)C	2321.1	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2[NH]1	2300.8	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O)C=C2N1[Si](C)(C)C	2329.9	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C	2344.6	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C(C(=O)O)=C2	2344.3	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C	2365.9	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C	2332.2	Standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C	2157.7	Standard polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2[NH]1	2617.7	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C(C(=O)O)=C2	2578.5	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C(C(=O)O)[NH]2)C=C1O	2583.7	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC2=CC(O)=C(O)C=C21	2571.3	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2[NH]1	2806.5	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]1	2793.7	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C(C)(C)C	2770.0	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C(C(=O)O)=C2	2860.2	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C2	2813.4	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C=C(C(=O)O)N2[Si](C)(C)C(C)(C)C	2814.1	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]1	3051.2	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2N1[Si](C)(C)C(C)(C)C	2967.8	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C	2958.5	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C2	3018.9	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C	3147.9	Semi standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C	3131.3	Standard non polar	33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C	2645.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-0900000000-86e3bb7f8c4c5358f1ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (3 TMS) - 70eV, Positive	splash10-00du-5329000000-6168733ed8a73f569928	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Positive-QTOF	splash10-002f-0900000000-4323f8e82f9ef2c149e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Positive-QTOF	splash10-0002-0900000000-5180e19b4ff79f8ccbe8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Positive-QTOF	splash10-01bc-3900000000-523d85a810268dbe9cf7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Negative-QTOF	splash10-0006-0900000000-6d7269d6d89c3eae16f9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Negative-QTOF	splash10-0005-0900000000-4d67dcdd279043d44620	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Negative-QTOF	splash10-006t-1900000000-968f54cfbf806d2e2389	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Negative-QTOF	splash10-0007-0900000000-7937a0f008a025981516	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Negative-QTOF	splash10-0002-0900000000-b0b74fab2c882d47700d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Negative-QTOF	splash10-00xs-2900000000-a0ec9715df089ba80b98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Positive-QTOF	splash10-0006-0900000000-b8d69868735567e6ffd7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Positive-QTOF	splash10-004l-0900000000-b28b84208bb53ec6a35b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Positive-QTOF	splash10-00fu-5900000000-f33eeedd7677021f68df	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

56DIHINDLCRBXLT

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Chioccara, Francesco; Novellino, Ettore. Biomimetic synthesis of 5,6-dihydroxyindole-2-carboxylic acid and of its benzyl ester. Synthetic Communications (1987), 17(15), 1815-21.

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Enzymes

Enzyme Details

1. Macrophage migration inhibitory factor

General function:: Involved in cell surface binding
Specific function:: Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:: MIF
Uniprot ID:: P14174
Molecular weight:: 12476.19

Reactions

L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic acid	details

Enzyme Details

2. L-dopachrome tautomerase

General function:: Involved in oxidoreductase activity
Specific function:: Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:: DCT
Uniprot ID:: P40126
Molecular weight:: 62928.215

Reactions

L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic acid	details

Enzyme Details

3. 5,6-dihydroxyindole-2-carboxylic acid oxidase

General function:: Involved in copper ion binding
Specific function:: Oxidation of 5,6-dihydroxyindole-2-carboxylic acid (DHICA) into indole-5,6-quinone-2-carboxylic acid. May regulate or influence the type of melanin synthesized
Gene Name:: TYRP1
Uniprot ID:: P17643
Molecular weight:: 60723.8

Showing metabocard for 5,6-Dihydroxyindole-2-carboxylic acid (HMDB0001253)

MOL for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

3D MOL for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

3D SDF for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

3D-SDF for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

PDB for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

3D PDB for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

SMILES for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

INCHI for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

Structure for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

3D Structure for HMDB0001253 (5,6-Dihydroxyindole-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions