Identification
Name6-hydroxydopa quinone
Accession NumberDB04334  (EXPT03094)
TypeSmall Molecule
GroupsExperimental
DescriptionNot 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
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 211.1715
Monoisotopic: 211.048072403
Chemical FormulaC9H9NO5
InChI KeyAGMJSPIGDFKRRO-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[C@@H](CC1=CC(=O)C(O)=CC1=O)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Membrane primary amine oxidaseProteinunknownNot AvailableHumanQ16853 details
Primary amine oxidaseProteinunknownNot AvailableEscherichia coli (strain K12)P46883 details
Phenylethylamine oxidaseProteinunknownNot AvailableArthrobacter globiformisP46881 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-alpha-amino acids
Alternative ParentsP-benzoquinones / Vinylogous acids / Amino acids / Monocarboxylic acids and derivatives / Enols / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
SubstituentsL-alpha-amino acid / P-benzoquinone / Quinone / Vinylogous acid / Ketone / Amino acid / Cyclic ketone / Carboxylic acid / Enol / Monocarboxylic acid or derivatives
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptorsnon-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-independent fashion. Has semicarbazide-sensitive (SSAO) monoamine oxidase activity. May play a role in adipogenesis.
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 June 11, 2017 20:54