2,3-Dihydroxy-Benzoic Acid

Identification

Name
2,3-Dihydroxy-Benzoic Acid
Accession Number
DB01672  (EXPT01121)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-27435
Categories
Not Available
UNII
70D5FBB392
CAS number
303-38-8
Weight
Average: 154.1201
Monoisotopic: 154.02660868
Chemical Formula
C7H6O4
InChI Key
GLDQAMYCGOIJDV-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
IUPAC Name
2,3-dihydroxybenzoic acid
SMILES
OC(=O)C1=CC=CC(O)=C1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2,3-dihydroxybenzoate-AMP ligaseNot AvailableBacillus subtilis (strain 168)
UNeutrophil gelatinase-associated lipocalinNot 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
PathwayCategory
2,3-Dihydroxybenzoate BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000397
KEGG Compound
C00196
PubChem Compound
19
PubChem Substance
46504857
ChemSpider
18
BindingDB
92456
ChEBI
18026
ChEMBL
CHEMBL1432
HET
DBH
PDB Entries
1l6m / 1md9 / 1mdb / 2why / 3by0 / 3cmp / 3i0a / 3k3l / 3sao / 3t1d
show 3 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
PropertyValueSource
melting point (°C)204 °CPhysProp
logP1.20HANSCH,C ET AL. (1995)
pKa2.91 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility6.88 mg/mLALOGPS
logP1.42ALOGPS
logP1.67ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.28 m3·mol-1ChemAxon
Polarizability13.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8051
Blood Brain Barrier-0.6225
Caco-2 permeable-0.5611
P-glycoprotein substrateNon-substrate0.6639
P-glycoprotein inhibitor INon-inhibitor0.9825
P-glycoprotein inhibitor IINon-inhibitor0.994
Renal organic cation transporterNon-inhibitor0.9415
CYP450 2C9 substrateNon-substrate0.8198
CYP450 2D6 substrateNon-substrate0.9193
CYP450 3A4 substrateNon-substrate0.7265
CYP450 1A2 substrateNon-inhibitor0.9274
CYP450 2C9 inhibitorNon-inhibitor0.9363
CYP450 2D6 inhibitorNon-inhibitor0.9693
CYP450 2C19 inhibitorNon-inhibitor0.9782
CYP450 3A4 inhibitorNon-inhibitor0.8427
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9318
Ames testNon AMES toxic0.9146
CarcinogenicityNon-carcinogens0.9177
BiodegradationReady biodegradable0.8936
Rat acute toxicity1.8670 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9821
hERG inhibition (predictor II)Non-inhibitor0.9599
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
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0a4i-0924000000-1ed6156dbe82344d29af
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0a4u-3922000000-0b326da278c57df03c1a
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4i-0924000000-1ed6156dbe82344d29af
GC-MS Spectrum - GC-MSGC-MSsplash10-0a4u-3922000000-0b326da278c57df03c1a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4l-0922000000-beddd6836f31d4813a14
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0zfr-0900000000-9d9306f70123d5d263ef
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0a4i-4900000000-702a14e999a2e830a9d5
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0a4i-7900000000-a88a9646fb3070aef98d
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
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0900000000-9bbc26971da28557772e
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0pb9-0900000000-7f5ec409ec11ea326d42
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0900000000-ba9640b66d655cdb3295
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0201-0900000000-40f4ec4c2b33e147f78b
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
Benzoic acids / Catechols / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides
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Substituents
Salicylic acid / Benzoic acid / Benzoyl / Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Vinylogous acid / Carboxylic acid derivative / Carboxylic acid
show 6 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dihydroxybenzoic acid (CHEBI:18026)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Ligase activity
Specific Function
Activation of the carboxylate group of 2,3-dihydroxy-benzoate (DHB), via ATP-dependent PPi exchange reactions, to the acyladenylate.
Gene Name
dhbE
Uniprot ID
P40871
Uniprot Name
2,3-dihydroxybenzoate-AMP ligase
Molecular Weight
59927.77 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
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Iron-trafficking protein involved in multiple processes such as apoptosis, innate immunity and renal development. Binds iron through association with 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderop...
Gene Name
LCN2
Uniprot ID
P80188
Uniprot Name
Neutrophil gelatinase-associated lipocalin
Molecular Weight
22587.915 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 October 01, 2018 13:07