Livestock Metabolome Database: Showing metabocard for Hydroxykynurenine (LMDB00232)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:16 UTC

Update Date

2016-07-20 20:58:26 UTC

Lmdb

LMDB00232

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydroxykynurenine

Description

Hydroxykynurenine, also known as OH-kynurenine, 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. Hydroxykynurenine is a very strong basic compound (based on its pKa). In humans, hydroxykynurenine is involved in tryptophan metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid	ChEBI
3-(3-Hydroxyanthraniloyl)alanine	ChEBI
3-Hydroxy-DL-kynurenine	ChEBI
2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoate	Generator
3-(3-Hydroxyanthraniloyl)-alanine	HMDB
3-Hydroxy-kynurenine	HMDB
3-Hydroxykynurenine	HMDB
DL-3-Hydroxykynurenine	HMDB
Hydroxykinurenine	HMDB
OH-Kynurenine	HMDB
3-Hydroxykynurenine, (DL)-isomer	HMDB
3-Hydroxykynurenine, (D)-isomer	HMDB
3-Hydroxykynurenine, (L)-isomer	HMDB

Chemical Formula

C₁₀H₁₂N₂O₄

Average Molecular Weight

224.2133

Monoisotopic Molecular Weight

224.079706882

IUPAC Name

2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid

Traditional Name

hydroxykynurenine

CAS Registry Number

484-78-6

SMILES

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

InChI Identifier

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

InChI Key

VCKPUUFAIGNJHC-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
Gamma-keto acid
O-aminophenol
Aryl alkyl ketone
Aniline or substituted anilines
Benzoyl
Aminophenol
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Keto acid
Beta-aminoketone
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Amino acid or derivatives
Amino acid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Amine
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxykynurenine (CHEBI:1547 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

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	-2.1	ALOGPS
logP	-2.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	0.99	ChemAxon
pKa (Strongest Basic)	8.9	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	21.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0692000000-b9c2999ae2687722738c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0692000000-b9c2999ae2687722738c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2900000000-204b3428485576e2be1b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0zfr-2190000000-7696628de35ae9a40c12	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0910000000-d216d77a1ba053893773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0910000000-d216d77a1ba053893773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-03di-0920000000-385b607aaff360ab6caa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03ea-1900000000-ef0fe807e674f9ebb6d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0900-4900000000-612a41c6275a8a19a249	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-08gi-0920000000-4b908956ed8a5664b1c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-052e-7900000000-96621f7c85b0781c4f57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-2900000000-73b312a84ece92c5b5e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-4900000000-bf8dda1c50f8619470f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-0930000000-d2d61a7429fefc483673	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-0920000000-bd92ed1676b4db71cee8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0690000000-2458bca60bd4d63d4e0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-2900000000-9f7c3e5d9fdd069332ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05y3-9600000000-0a276981035bdfdaa384	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a7l-0980000000-d29afe0493d7b1747ece	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0c0r-0910000000-05ae10fbc19a32189675	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-03k9-1900000000-0a8a8247ae2ccdceccc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03di-6900000000-d831db1fd30714ed7af0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004j-9400000000-b9afef7c45866b074926	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0190000000-ff6859f21558ded760b7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03xr-0900000000-96098b3be4cea5d8ba14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-006x-0900000000-6393e30c9fa764800712	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0ik9-0900000000-4f9bd3b6476d74c41a74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-972b9ebadf10c99787c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-01qa-0900000000-301763df64398d3bd889	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	22242129	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000732

FooDB ID

FDB022210

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5700

PDB ID

Not Available

Wikipedia Link

3-Hydroxykynurenine

Chemspider ID

ChEBI ID

1547

PubChem Compound ID

Kegg Compound ID

C02794

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Guidetti P, Bates GP, Graham RK, Hayden MR, Leavitt BR, MacDonald ME, Slow EJ, Wheeler VC, Woodman B, Schwarcz R: Elevated brain 3-hydroxykynurenine and quinolinate levels in Huntington disease mice. Neurobiol Dis. 2006 Jul;23(1):190-7. Epub 2006 May 12. [16697652 ]

Showing metabocard for Hydroxykynurenine (LMDB00232)

Structure for LMDB00232 (Hydroxykynurenine)