Kynurenine

Identification

Generic Name
Kynurenine
DrugBank Accession Number
DB02070
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 208.2139
Monoisotopic: 208.08479226
Chemical Formula
C10H12N2O3
Synonyms
  • (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
  • 3-Anthraniloyl-L-alanine
  • L-kynurenine
External IDs
  • CCRIS 4425

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Butyrophenones / L-alpha-amino acids / Gamma-keto acids and derivatives / Benzoyl derivatives / Aryl alkyl ketones / Aniline and substituted anilines / Beta-amino ketones / Vinylogous amides / Amino acids / Monocarboxylic acids and derivatives
show 5 more
Substituents
Alkyl-phenylketone / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, kynurenine (CHEBI:16946)
Affected organisms
Not Available

Chemical Identifiers

UNII
02JW4J5R44
CAS number
2922-83-0
InChI Key
YGPSJZOEDVAXAB-QMMMGPOBSA-N
InChI
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
IUPAC Name
(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0000684
KEGG Compound
C00328
PubChem Compound
161166
PubChem Substance
46507622
ChemSpider
141580
BindingDB
31880
ChEBI
57959
ChEMBL
CHEMBL498416
ZINC
ZINC000000895186
PDBe Ligand
KYN
Wikipedia
Kynurenine
PDB Entries
1t5m / 1t5n / 1xt7 / 2r2n / 2vov / 2vox / 3av7 / 3e2z / 4bz4 / 5nak
show 8 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherHeadache1
1RecruitingBasic ScienceDrug Drug Interaction (DDI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.67 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.9Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19Chemaxon
pKa (Strongest Basic)8.96Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.41 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity55.05 m3·mol-1Chemaxon
Polarizability20.59 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.64
Blood Brain Barrier-0.6044
Caco-2 permeable-0.6701
P-glycoprotein substrateNon-substrate0.6651
P-glycoprotein inhibitor INon-inhibitor0.9296
P-glycoprotein inhibitor IINon-inhibitor0.9811
Renal organic cation transporterNon-inhibitor0.9436
CYP450 2C9 substrateNon-substrate0.8208
CYP450 2D6 substrateNon-substrate0.8674
CYP450 3A4 substrateNon-substrate0.7961
CYP450 1A2 substrateNon-inhibitor0.9409
CYP450 2C9 inhibitorNon-inhibitor0.95
CYP450 2D6 inhibitorNon-inhibitor0.954
CYP450 2C19 inhibitorNon-inhibitor0.954
CYP450 3A4 inhibitorNon-inhibitor0.96
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9772
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8487
BiodegradationReady biodegradable0.5252
Rat acute toxicity1.8739 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9725
hERG inhibition (predictor II)Non-inhibitor0.9518
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014l-0931000000-29fa7c323b035cb399d3
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dl-9500000000-d7bf6a26c74e0dcabf40
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014l-0931000000-29fa7c323b035cb399d3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014l-0931000000-a43ae0acafac266101c4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-1910000000-fdc25d09b4da4b1d7657
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0006-2910000000-366ce08b5736d68dfad0
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-01bd-5900000000-c18e10be7e029474cf03
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00kf-9300000000-0f8238d38819f6f30d12
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0a4i-0790000000-3fa45266412288bf1c62
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0007-3900000000-a66f45aff81960af7575
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00xv-5900000000-15442ec5aaef005401ae
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00r7-7900000000-0833fe9d2739d329f197
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9400000000-d5d45364462a730de436
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0006-0900000000-13929f0bde71b6326d3f
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0f6w-2900000000-b2d4f361ffee9fd93bb7
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-004j-0900000000-96930a886f7bbcc44df3
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000i-0900000000-2441a358973abdb063da
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0udi-0900000000-dc4fee4751d629575157
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0900000000-4ec06cc06a3eab2625d6
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0900000000-319acefac99779fa7552
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0059-0890000000-4280b92b875a6f754a91
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0059-0890000000-664e2c8904363418682e
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00dj-0139000000-aa6188977ba2f460f5bc
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00dj-0139000000-ee71a364df13bd095feb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0920000000-607dee4a3efb718339b6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00ds-0900000000-19c838d5478f570ffb50
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00r2-0900000000-275bef748b04de950909
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ba-1900000000-64ee050c4ce47392ea0e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01bd-2900000000-069fda767e994e9546a0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0790000000-3fa45266412288bf1c62
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0007-3900000000-a66f45aff81960af7575
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00xv-5900000000-37f1dd3063f8363f8d71
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r7-7900000000-4f3a2d7ad57bfa7eeb24
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9400000000-d5d45364462a730de436
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0006-0900000000-35275991e526ffdfcaf6
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0006-0900000000-18c5c7fabe5faeb6acfe
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-1900000000-8af401eac841ea498e90
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-1900000000-223f2a2cb57eefe67ffc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-053r-0193000000-7caaee57b13f2d541ba1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0291000000-77cdbde7a930024fafed
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-074j-0910000000-64146ef6e86f89a56769
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-007n-4910000000-d2c7bdc4573133eb161f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2900000000-1dbfd915128ba8b2e01a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-7900000000-521cbbb8ffda1f041b4e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-9300000000-5411f0425dbd11625cfb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-1ee7a6213cf30a4f2006
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-152.4929719
predicted
DarkChem Lite v0.1.0
[M-H]-152.3894719
predicted
DarkChem Lite v0.1.0
[M-H]-141.86374
predicted
DeepCCS 1.0 (2019)
[M+H]+153.0688719
predicted
DarkChem Lite v0.1.0
[M+H]+153.0375719
predicted
DarkChem Lite v0.1.0
[M+H]+144.2593
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.2833719
predicted
DarkChem Lite v0.1.0
[M+Na]+152.4309719
predicted
DarkChem Lite v0.1.0
[M+Na]+150.26167
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52