6-hydroxydopa quinone

Identification

Name
6-hydroxydopa quinone
Accession Number
DB04334  (EXPT03094)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2,4,5-trihydroxyphenylalanine quinone
  • 5-(2-carboxy-2-aminoethyl)-2-hydroxy-1,4-benzoquinone
  • 5-(2-carboxy-2-aminoethyl)-4-hydroxy-1,2-benzoquinone
  • Topa quinone
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 211.1715
Monoisotopic: 211.048072403
Chemical Formula
C9H9NO5
InChI Key
AGMJSPIGDFKRRO-YFKPBYRVSA-N
InChI
InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,13H,1,10H2,(H,14,15)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-3-(4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)propanoic acid
SMILES
N[[email protected]@H](CC1=CC(=O)C(O)=CC1=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMembrane primary amine oxidaseNot AvailableHuman
UPrimary amine oxidaseNot AvailableEscherichia coli (strain K12)
UPhenylethylamine oxidaseNot AvailableArthrobacter globiformis
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
123871
PubChem Substance
46505126
ChemSpider
16744234
ChEBI
36076
HET
TPQ
PDB Entries
1a2v / 1av4 / 1avl / 1dyu / 1iqx / 1iqy / 1iu7 / 1ivw / 1ivx / 1jrq
show 50 more

Clinical Trials

Clinical Trials
Not Available

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 Solubility2.01 mg/mLALOGPS
logP-2ALOGPS
logP-2.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.37 m3·mol-1ChemAxon
Polarizability19.04 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9061
Blood Brain Barrier-0.9277
Caco-2 permeable-0.7825
P-glycoprotein substrateNon-substrate0.5775
P-glycoprotein inhibitor INon-inhibitor0.9227
P-glycoprotein inhibitor IINon-inhibitor0.9701
Renal organic cation transporterNon-inhibitor0.9199
CYP450 2C9 substrateNon-substrate0.903
CYP450 2D6 substrateNon-substrate0.8728
CYP450 3A4 substrateNon-substrate0.6898
CYP450 1A2 substrateNon-inhibitor0.9402
CYP450 2C9 inhibitorNon-inhibitor0.9502
CYP450 2D6 inhibitorNon-inhibitor0.9228
CYP450 2C19 inhibitorNon-inhibitor0.9435
CYP450 3A4 inhibitorNon-inhibitor0.942
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9866
Ames testNon AMES toxic0.7644
CarcinogenicityNon-carcinogens0.9343
BiodegradationReady biodegradable0.7104
Rat acute toxicity1.9074 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9749
hERG inhibition (predictor II)Non-inhibitor0.9821
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
P-benzoquinones / Vinylogous acids / Amino acids / Monocarboxylic acids and derivatives / Enols / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
L-alpha-amino acid / P-benzoquinone / Quinone / Vinylogous acid / Ketone / Amino acid / Cyclic ketone / Carboxylic acid / Enol / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, topaquinone (CHEBI:36076)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
Cell adhesion protein that participates in lymphocyte extravasation and recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-in...
Gene Name
AOC3
Uniprot ID
Q16853
Uniprot Name
Membrane primary amine oxidase
Molecular Weight
84621.27 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
The enzyme prefers aromatic over aliphatic amines.
Gene Name
tynA
Uniprot ID
P46883
Uniprot Name
Primary amine oxidase
Molecular Weight
84378.17 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P46881
Uniprot Name
Phenylethylamine oxidase
Molecular Weight
70645.405 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:26