MiMeDB: Showing metabocard for 5-Hydroxykynurenine (MMDBc0047970)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:19:45 UTC

Update Date

2022-09-01 02:13:45 UTC

Metabolite ID

MMDBc0047970

Metabolite Identification

Common Name

5-Hydroxykynurenine

Description

5-Hydroxykynurenine is found in the tryptophan metabolism pathway. It is created from 5-Hydroxy-N-formylkynurenine through the action of arylformamidase [EC:3.5.1.9]. 5-Hydroxykynurenine is then converted to 5-Hydroxykynurenamine by the action of dopa decarboxylase [EC:4.1.1.28].

Structure

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


  Mrv0541 02241204052D          

 16 16  0  0  0  0            999 V2000
   12.7992  -12.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -11.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116  -10.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -10.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7992   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2116   -7.9174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743   -8.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618   -9.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9743  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618  -10.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0366  -12.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -12.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4491  -11.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047970

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)

> <INCHI_KEY>
OTDQYOVYQQZAJL-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O4

> <MOLECULAR_WEIGHT>
224.2133

> <EXACT_MASS>
224.079706882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.525399736709765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-2.17

> <JCHEM_LOGP>
-2.2166730141507074

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.89292664584021

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9781795743085331

> <JCHEM_PKA_STRONGEST_BASIC>
8.908716626078787

> <JCHEM_POLAR_SURFACE_AREA>
126.64000000000001

> <JCHEM_REFRACTIVITY>
57.03110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxykynurenine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      23.892 -24.115   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      24.662 -22.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.892 -21.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.662 -20.114   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      26.202 -20.114   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.892 -18.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.662 -17.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.892 -16.113   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      24.662 -14.779   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.352 -16.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.582 -17.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.352 -18.781   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      21.582 -20.114   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      26.202 -22.781   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      26.972 -24.115   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      26.972 -21.447   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12    6   11   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0012819
HETATM    1  N1  UNL     1      -1.664  -2.424  -0.758  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.083  -1.132  -0.394  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.407  -0.888  -0.127  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.817   0.383   0.229  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.872   1.377   0.304  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.267   2.648   0.658  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.529   1.121   0.031  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.117  -0.138  -0.322  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.271  -0.457  -0.596  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.571  -1.668  -0.888  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.406   0.480  -0.577  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.491  -0.029   0.356  1.00  0.00           C  
HETATM   13  N2  UNL     1       3.022  -1.309  -0.005  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.532   1.012   0.566  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.100   2.173   0.843  1.00  0.00           O  
HETATM   16  O4  UNL     1       4.883   0.722   0.462  1.00  0.00           O  
HETATM   17  H1  UNL     1      -1.588  -3.154  -0.033  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.435  -2.636  -1.740  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.159  -1.671  -0.186  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.868   0.539   0.431  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.616   3.429   0.735  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.834   1.936   0.106  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.072   1.474  -0.296  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.865   0.530  -1.615  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.029  -0.170   1.383  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.101  -1.490  -1.010  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.438  -2.056   0.429  1.00  0.00           H  
HETATM   28  H12 UNL     1       5.473   1.400  -0.001  1.00  0.00           H  
CONECT    1    2   17   18
CONECT    2    3    3    8
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6    7
CONECT    6   21
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   23   24
CONECT   12   13   14   25
CONECT   13   26   27
CONECT   14   15   15   16
CONECT   16   28
END

Synonyms

Value	Source
2-Amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid	ChEBI
2-Amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoate	Generator
5-Hydroxy-L-kynurenine	HMDB
5-Hydroxykynurenine, (L)-isomer	HMDB

Molecular Formula

C₁₀H₁₂N₂O₄

Average Mass

224.2133

Monoisotopic Mass

224.079706882

IUPAC Name

2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid

Traditional Name

5-hydroxykynurenine

CAS Registry Number

720-00-3

SMILES

NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)

InChI Key

OTDQYOVYQQZAJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Alpha-amino acid
Alpha-amino acid or derivatives
P-aminophenol
Aminophenol
Benzoyl
Gamma-keto acid
Aryl alkyl ketone
Aniline or substituted anilines
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Beta-aminoketone
Keto acid
Vinylogous amide
Amino acid
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Amine
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxykynurenine (CHEBI:2076 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.12 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.98	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.03 m³·mol⁻¹	ChemAxon
Polarizability	21.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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	splash10-000i-2900000000-759106525958c7559c0e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9167000000-abb2f436c993df4c1d30	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	splash10-056r-0890000000-dfa042db46858117582c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03mr-2900000000-c8e51ba13da85857d00b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-5900000000-a8fdd6f4771588adc784	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1090000000-1b6f8b69fc5d1440121f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9560000000-3a0c724edce767136c71	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-6900000000-43fed4337f093b9e8e92	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0590000000-3491ab58bac06eaf1c8b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06vi-1900000000-2eca61562922fc2223ee	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-8900000000-b87794b8cc3c797a29c6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05fr-0590000000-5ef5be198ab9accfc633	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-4c1bf27c3b9ad731646d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9600000000-824917bfb14bccd67e63	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

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
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo sapiens
MMDBp0194173	Kynurenine formamidase	Unknown	Q63HM1	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000121	5-Hydroxykynurenine	5-Hydroxykynurenamine	Not Available	5-Hydroxykynurenamine Decarboxy-Lyase	VMH	30371894
MMDBr0010404	5-Hydroxy-N-formylkynurenine	5-Hydroxykynurenine	Arylformamidase	Arylformamidase	VMH	30371894

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	46	Human feces; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	105	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	44	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	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
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0012819

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029180

KNApSAcK ID

Not Available

Chemspider ID

389616

KEGG Compound ID

C05651

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Hydroxykynurenine

METLIN ID

Not Available

PubChem Compound

440745

PDB ID

Not Available

ChEBI ID

2076

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 5-Hydroxykynurenine (MMDBc0047970)

MOL for #<Metabolite:0x00007f5a57c6e6f8>

3D MOL for #<Metabolite:0x00007f5a57c6e6f8>

3D SDF for #<Metabolite:0x00007f5a57c6e6f8>

3D-SDF for #<Metabolite:0x00007f5a57c6e6f8>

PDB for #<Metabolite:0x00007f5a57c6e6f8>

3D PDB for #<Metabolite:0x00007f5a57c6e6f8>

SMILES for #<Metabolite:0x00007f5a57c6e6f8>

INCHI for #<Metabolite:0x00007f5a57c6e6f8>

Structure for #<Metabolite:0x00007f5a57c6e6f8>

3D Structure for #<Metabolite:0x00007f5a57c6e6f8>