NAV

2-Hydroxy-Tryptophan

Identification

Generic Name
2-Hydroxy-Tryptophan
DrugBank Accession Number
DB03679
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 220.2246
Monoisotopic: 220.08479226
Chemical Formula
C11H12N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UQuinohemoprotein ethanol dehydrogenase type-1Not AvailableComamonas testosteroni
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
Not Available
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indolyl carboxylic acids and derivatives
Alternative Parents
3-alkylindoles / L-alpha-amino acids / Hydroxyindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives / Azacyclic compounds
show 6 more
Substituents
3-alkylindole / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tryptophan derivative, 2-hydroxytryptophan (CHEBI:74690)
Affected organisms
Not Available

Chemical Identifiers

UNII
TCB9GM9U3X
CAS number
Not Available
InChI Key
VAUYGGXCASQWHK-QMMMGPOBSA-N
InChI
InChI=1S/C11H12N2O3/c12-8(11(15)16)5-7-6-3-1-2-4-9(6)13-10(7)14/h1-4,8,13-14H,5,12H2,(H,15,16)/t8-/m0/s1
IUPAC Name
(2S)-2-amino-3-(2-hydroxy-1H-indol-3-yl)propanoic acid
SMILES
[H][C@](N)(CC1=C(O)NC2=CC=CC=C12)C(O)=O

References

General References
Not Available
PubChem Compound
17754204
PubChem Substance
46508982
ChemSpider
16744237
ChEBI
74690
ZINC
ZINC000100020157
PDBe Ligand
TRO
PDB Entries
1g3p / 1kb0 / 3nzj / 4cp9 / 4cpb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility4.5 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.3Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.2Chemaxon
pKa (Strongest Basic)8.64Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area99.34 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity57.44 m3·mol-1Chemaxon
Polarizability22.11 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9641
Blood Brain Barrier+0.8951
Caco-2 permeable-0.7447
P-glycoprotein substrateNon-substrate0.5473
P-glycoprotein inhibitor INon-inhibitor0.9968
P-glycoprotein inhibitor IINon-inhibitor0.9973
Renal organic cation transporterNon-inhibitor0.9206
CYP450 2C9 substrateNon-substrate0.767
CYP450 2D6 substrateNon-substrate0.794
CYP450 3A4 substrateNon-substrate0.6717
CYP450 1A2 substrateNon-inhibitor0.8141
CYP450 2C9 inhibitorNon-inhibitor0.9087
CYP450 2D6 inhibitorNon-inhibitor0.9117
CYP450 2C19 inhibitorNon-inhibitor0.9187
CYP450 3A4 inhibitorNon-inhibitor0.949
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9356
Ames testNon AMES toxic0.9229
CarcinogenicityNon-carcinogens0.956
BiodegradationNot ready biodegradable0.8303
Rat acute toxicity2.3096 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9969
hERG inhibition (predictor II)Non-inhibitor0.9453
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0095-4920000000-522b053e9c27faa11578
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0190000000-8314dddd87cda45e6feb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9040000000-149455f42678014ff3bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05i0-0950000000-e1730fd0c099607fb143
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-8930000000-695727cb9bf17372626b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-b04a8910406ee24721f5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kai-0900000000-612d65dbfd933e51b3a9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-146.49327
predicted
DeepCCS 1.0 (2019)
[M+H]+148.88884
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.80136
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Quinohemoprotein ethanol dehydrogenase type-1
Kind
Protein
Organism
Comamonas testosteroni
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on ch-oh group of donors
Specific Function
Catalyzes the dye-linked oxidation of primary alcohols to the corresponding aldehydes and the (subsequent) oxidation of the aldehydes to carboxylic acids.
Gene Name
qheDH
Uniprot ID
Q46444
Uniprot Name
Quinohemoprotein ethanol dehydrogenase type-1
Molecular Weight
76822.435 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

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