2-HYDROXY-3,5-DIIODOBENZOIC ACID

Identification

Name
2-HYDROXY-3,5-DIIODOBENZOIC ACID
Accession Number
DB04674
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
1496OH15B6
CAS number
Not Available
Weight
Average: 389.9138
Monoisotopic: 389.824980834
Chemical Formula
C7H4I2O3
InChI Key
DHZVWQPHNWDCFS-UHFFFAOYSA-N
InChI
InChI=1S/C7H4I2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)
IUPAC Name
2-hydroxy-3,5-diiodobenzoic acid
SMILES
OC(=O)C1=C(O)C(I)=CC(I)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEndothelin-1 receptorNot AvailableHuman
UAldo-keto reductase family 1 member C1Not AvailableHuman
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
8631
PubChem Substance
46507861
ChemSpider
8310
ChEMBL
CHEMBL1232243
HET
DIU
PDB Entries
2bxl / 3b56 / 4j2v / 4jk4 / 4luh / 5osw

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 Solubility0.155 mg/mLALOGPS
logP3.13ALOGPS
logP3.84ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.51ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.02 m3·mol-1ChemAxon
Polarizability23.86 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8923
Blood Brain Barrier+0.7116
Caco-2 permeable+0.8475
P-glycoprotein substrateNon-substrate0.7385
P-glycoprotein inhibitor INon-inhibitor0.9801
P-glycoprotein inhibitor IINon-inhibitor0.9958
Renal organic cation transporterNon-inhibitor0.9241
CYP450 2C9 substrateNon-substrate0.8176
CYP450 2D6 substrateNon-substrate0.9158
CYP450 3A4 substrateNon-substrate0.7441
CYP450 1A2 substrateNon-inhibitor0.8298
CYP450 2C9 inhibitorNon-inhibitor0.5384
CYP450 2D6 inhibitorNon-inhibitor0.946
CYP450 2C19 inhibitorNon-inhibitor0.8936
CYP450 3A4 inhibitorNon-inhibitor0.8392
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.815
Ames testNon AMES toxic0.9401
CarcinogenicityNon-carcinogens0.8516
BiodegradationNot ready biodegradable0.9071
Rat acute toxicity2.3995 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9588
hERG inhibition (predictor II)Non-inhibitor0.9727
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 salicylic acids. These are ortho-hydroxylated benzoic acids.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Salicylic acids
Alternative Parents
Halobenzoic acids / 3-halobenzoic acids / Benzoic acids / P-iodophenols / O-iodophenols / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous acids / Monocarboxylic acids and derivatives
show 5 more
Substituents
Salicylic acid / 3-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / 3-halobenzoic acid / Halobenzoic acid / Benzoic acid / 4-halophenol / 2-iodophenol / 2-halophenol / 4-iodophenol
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
Receptor for endothelin-1. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of binding affinities for ET-A is:...
Gene Name
EDNRA
Uniprot ID
P25101
Uniprot Name
Endothelin-1 receptor
Molecular Weight
48721.76 Da
References
  1. Blandin V, Vigne P, Breittmayer JP, Frelin C: Allosteric inhibition of endothelin ETA receptors by 3, 5-dibromosalicylic acid. Mol Pharmacol. 2000 Dec;58(6):1461-9. [PubMed:11093786]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
Gene Name
AKR1C1
Uniprot ID
Q04828
Uniprot Name
Aldo-keto reductase family 1 member C1
Molecular Weight
36788.02 Da
References
  1. Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [PubMed:18045204]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name
TTR
Uniprot ID
P02766
Uniprot Name
Transthyretin
Molecular Weight
15886.88 Da
References
  1. Gales L, Almeida MR, Arsequell G, Valencia G, Saraiva MJ, Damas AM: Iodination of salicylic acid improves its binding to transthyretin. Biochim Biophys Acta. 2008 Mar;1784(3):512-7. Epub 2007 Dec 3. [PubMed:18155178]

Drug created on September 11, 2007 11:49 / Updated on December 01, 2017 15:31