3,4-Dihydroxybenzoic Acid

Identification

Name
3,4-Dihydroxybenzoic Acid
Accession Number
DB03946  (EXPT01187)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-16631
Categories
UNII
36R5QJ8L4B
CAS number
99-50-3
Weight
Average: 154.1201
Monoisotopic: 154.02660868
Chemical Formula
C7H6O4
InChI Key
YQUVCSBJEUQKSH-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
IUPAC Name
3,4-dihydroxybenzoic acid
SMILES
OC(=O)C1=CC=C(O)C(O)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with 3,4-Dihydroxybenzoic Acid.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with 3,4-Dihydroxybenzoic Acid.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with 3,4-Dihydroxybenzoic Acid.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of 3,4-Dihydroxybenzoic Acid.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01856
KEGG Compound
C00230
PubChem Compound
72
PubChem Substance
46505638
ChemSpider
71
BindingDB
50100861
ChEBI
36062
ChEMBL
CHEMBL37537
HET
DHB
PDB Entries
1b4u / 1eob / 1n8q / 1phh / 1ykl / 1ykn / 1ykp / 2bsl / 2buv / 2bv0
show 15 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)221 dec °CPhysProp
water solubility1.82E+004 mg/L (at 14 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.86HANSCH,C ET AL. (1995)
pKa4.26 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility12.4 mg/mLALOGPS
logP1.32ALOGPS
logP1.02ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
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
Polarizability13.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8811
Blood Brain Barrier-0.6376
Caco-2 permeable+0.5553
P-glycoprotein substrateNon-substrate0.6756
P-glycoprotein inhibitor INon-inhibitor0.9829
P-glycoprotein inhibitor IINon-inhibitor0.9948
Renal organic cation transporterNon-inhibitor0.9377
CYP450 2C9 substrateNon-substrate0.8227
CYP450 2D6 substrateNon-substrate0.9151
CYP450 3A4 substrateNon-substrate0.7227
CYP450 1A2 substrateNon-inhibitor0.9545
CYP450 2C9 inhibitorNon-inhibitor0.9568
CYP450 2D6 inhibitorNon-inhibitor0.9636
CYP450 2C19 inhibitorNon-inhibitor0.9707
CYP450 3A4 inhibitorNon-inhibitor0.9535
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9564
Ames testNon AMES toxic0.9326
CarcinogenicityNon-carcinogens0.9154
BiodegradationReady biodegradable0.8871
Rat acute toxicity1.6414 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9818
hERG inhibition (predictor II)Non-inhibitor0.9508
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) (3 TMS)GC-MSsplash10-0006-0913000000-0933eeed3701393aa41f
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0006-0911000000-ca1452bfe34749c0d8c1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00dl-9711000000-595a58baf84bb73670ae
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0006-4912000000-a095cbdb4d3809a9b775
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0gb9-9800000000-f08a8e55f19d388091c0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0913000000-0933eeed3701393aa41f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0911000000-ca1452bfe34749c0d8c1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dl-9711000000-595a58baf84bb73670ae
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-4912000000-a095cbdb4d3809a9b775
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-0911000000-c141d09a094e57440cd4
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-0900000000-9e8a76eec66c42952ee9
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0296-9100000000-145f71b183841a31fdc8
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014i-9000000000-9044e5839d8d0b8f8ee6
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-0gb9-9800000000-f08a8e55f19d388091c0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-0900000000-58c9b8232fbc187217d4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0900000000-99ac3661fc7809f28796
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0900000000-df55ffdd340947acfac9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pc9-9500000000-201668ae66ab0379946f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0900000000-99ac3661fc7809f28796
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0900000000-df55ffdd340947acfac9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pc9-9500000000-201668ae66ab0379946f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-0595d63853a488b9c6cf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-0900000000-d794b62eb087aaa84f94
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9700000000-32a6fa42639cb300cdc9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-0595d63853a488b9c6cf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-0900000000-d794b62eb087aaa84f94
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9700000000-32a6fa42639cb300cdc9
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0900000000-58c9b8232fbc187217d4
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0a4i-0900000000-43a650326b83e2dfe589
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0900000000-61ebd9558aeeb60dda89
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hydroxybenzoic acid derivatives
Alternative Parents
Benzoic acids / Catechols / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Dihydroxybenzoic acid / Hydroxybenzoic acid / Benzoic acid / Benzoyl / Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Carboxylic acid derivative / Carboxylic acid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catechols, dihydroxybenzoic acid (CHEBI:36062)

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:35