NAV

8-Hydroxy-4-(1-Hydroxyethyl)Quinoline-2-Carboxylic Acid

Identification

Generic Name
8-Hydroxy-4-(1-Hydroxyethyl)Quinoline-2-Carboxylic Acid
DrugBank Accession Number
DB02566
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 235.2359
Monoisotopic: 235.084457909
Chemical Formula
C12H13NO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThiostreptonNot AvailableStreptomyces azureus
U50S ribosomal protein L11Not AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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 quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Hydroquinolines / Pyridinecarboxylic acids / Heteroaromatic compounds / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Alcohol / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Dihydroquinoline / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FCGZNXGKWUHBKD-WKEGUHRASA-N
InChI
InChI=1S/C12H13NO4/c1-6(14)8-5-9(12(16)17)13-11-7(8)3-2-4-10(11)15/h2-3,5-6,10,14-15H,4H2,1H3,(H,16,17)/t6-,10-/m0/s1
IUPAC Name
(8S)-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7,8-dihydroquinoline-2-carboxylic acid
SMILES
[H][C@@](C)(O)C1=CC(=NC2=C1C=CC[C@]2([H])O)C(O)=O

References

General References
Not Available
PubChem Compound
5289243
PubChem Substance
46504771
ChemSpider
4451244
ZINC
ZINC000006929734
PDBe Ligand
QUA
PDB Entries
1e9w / 1oln / 2jq7 / 2l2w / 2l2x / 2l2y / 2l2z / 3cf5 / 4hp2 / 5d8h …
show 1 more

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 Solubility2.99 mg/mLALOGPS
logP0.31ALOGPS
logP-1.5Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.05Chemaxon
pKa (Strongest Basic)6.64Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area90.65 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity61.69 m3·mol-1Chemaxon
Polarizability23.66 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.993
Blood Brain Barrier+0.5978
Caco-2 permeable+0.5991
P-glycoprotein substrateSubstrate0.5592
P-glycoprotein inhibitor INon-inhibitor0.9517
P-glycoprotein inhibitor IINon-inhibitor0.9878
Renal organic cation transporterNon-inhibitor0.9166
CYP450 2C9 substrateNon-substrate0.688
CYP450 2D6 substrateNon-substrate0.7967
CYP450 3A4 substrateNon-substrate0.5943
CYP450 1A2 substrateNon-inhibitor0.75
CYP450 2C9 inhibitorNon-inhibitor0.8497
CYP450 2D6 inhibitorNon-inhibitor0.9326
CYP450 2C19 inhibitorNon-inhibitor0.8483
CYP450 3A4 inhibitorNon-inhibitor0.8898
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9228
Ames testNon AMES toxic0.8617
CarcinogenicityNon-carcinogens0.9681
BiodegradationNot ready biodegradable0.7601
Rat acute toxicity2.4023 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9822
hERG inhibition (predictor II)Non-inhibitor0.9316
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-MSsplash10-01bc-0950000000-0bde898c8d1ecf149f9e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0090000000-cba6352a202c897255ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0950000000-bbd394e486bf1ff412d8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0890000000-dcbc47fe03b7f7d9f4e0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0910000000-e9773705731693765ba1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0910000000-bbf560f12c055f3c46a7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03k9-0900000000-d42d4c2fbf552e277c62
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]-152.0304
predicted
DeepCCS 1.0 (2019)
[M+H]+154.3884
predicted
DeepCCS 1.0 (2019)
[M+Na]+161.27142
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thiostrepton
Kind
Protein
Organism
Streptomyces azureus
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Has bacteriocidal activity. Inhibits bacterial protein biosynthesis by acting on the elongation factor Tu (EF-Tu) (By similarity).
Gene Name
tpdA
Uniprot ID
P0C8P8
Uniprot Name
Thiostrepton
Molecular Weight
7550.295 Da
References
  1. 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. [Article]
Details2. 50S ribosomal protein L11
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Structural constituent of ribosome
Specific Function
Forms part of the ribosomal stalk which helps the ribosome interact with GTP-bound translation factors.
Gene Name
rplK
Uniprot ID
P29395
Uniprot Name
50S ribosomal protein L11
Molecular Weight
15088.79 Da
References
  1. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:43