NAV

3,6-dihydroxy-xanthene-9-propionic acid

Identification

Generic Name
3,6-dihydroxy-xanthene-9-propionic acid
DrugBank Accession Number
DB01644
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 286.2794
Monoisotopic: 286.084123558
Chemical Formula
C16H14O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutathione reductase, mitochondrialNot AvailableHumans
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 xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Xanthenes
Alternative Parents
Diarylethers / 1-hydroxy-2-unsubstituted benzenoids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-hydroxy-2-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diaryl ether / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PFQGLFBMMPZYEU-UHFFFAOYSA-N
InChI
InChI=1S/C16H14O5/c17-9-1-3-12-11(5-6-16(19)20)13-4-2-10(18)8-15(13)21-14(12)7-9/h1-4,7-8,11,17-18H,5-6H2,(H,19,20)
IUPAC Name
3-(3,6-dihydroxy-9H-xanthen-9-yl)propanoic acid
SMILES
OC(=O)CCC1C2=CC=C(O)C=C2OC2=C1C=CC(O)=C2

References

General References
Not Available
PubChem Compound
449159
PubChem Substance
46507003
ChemSpider
395767
ZINC
ZINC000031977026
PDBe Ligand
HXP
PDB Entries
1xan

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 Solubility0.0589 mg/mLALOGPS
logP2.58ALOGPS
logP2.84Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.6Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.99 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity75.36 m3·mol-1Chemaxon
Polarizability28.86 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8899
Blood Brain Barrier+0.7847
Caco-2 permeable+0.5924
P-glycoprotein substrateSubstrate0.5813
P-glycoprotein inhibitor INon-inhibitor0.9403
P-glycoprotein inhibitor IINon-inhibitor0.9104
Renal organic cation transporterNon-inhibitor0.8723
CYP450 2C9 substrateNon-substrate0.8022
CYP450 2D6 substrateNon-substrate0.8632
CYP450 3A4 substrateNon-substrate0.6599
CYP450 1A2 substrateNon-inhibitor0.6665
CYP450 2C9 inhibitorNon-inhibitor0.8457
CYP450 2D6 inhibitorNon-inhibitor0.8845
CYP450 2C19 inhibitorNon-inhibitor0.7023
CYP450 3A4 inhibitorNon-inhibitor0.8015
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9025
Ames testNon AMES toxic0.8218
CarcinogenicityNon-carcinogens0.9673
BiodegradationReady biodegradable0.5483
Rat acute toxicity2.7610 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8926
hERG inhibition (predictor II)Non-inhibitor0.8758
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-MSsplash10-03xu-1290000000-9ee2af0f9ec2bc55617a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0090000000-5b81a96df7bc074c8a9a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-8090000000-f8e1794d8214666f7117
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0290000000-83385bf1eb4937a6ada5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fu-2090000000-b806acfed3e119f140ab
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0api-0390000000-e3f84651a1d57050b833
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06r6-8690000000-7bd2d1da46f525495bef
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]-163.15466
predicted
DeepCCS 1.0 (2019)
[M+H]+165.51266
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.60582
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutathione reductase, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Maintains high levels of reduced glutathione in the cytosol.
Gene Name
GSR
Uniprot ID
P00390
Uniprot Name
Glutathione reductase, mitochondrial
Molecular Weight
56256.565 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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51