Protocatechualdehyde

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Protocatechualdehyde
Accession Number
DB11268
Type
Small Molecule
Groups
Approved
Description

Also known as protocatechuic aldehyde, protocatechualdehyde is a naturally-occuring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza [1]. Protocatechualdehyde possesses antiproliferative and pro-apoptotic properties against human breast cancer cells and colorectal cancer cells by reducing the expression of pro-oncogenes β-catenin and cyclin D1.

Structure
Thumb
Synonyms
  • 3,4-dihydroxybenzaldehyde
  • protocatechuic aldehyde
  • Rancinamycin IV
External IDs
NSC-22961
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
O Hui White Extreme CellightEmulsion0.0315 mL/100mLTopicalLg Household & Health Care Ltd.2011-03-07Not applicableUs
O Hui White Extreme CellightCream0.032 mL/100mLTopicalLg Household & Health Care Ltd.2011-03-16Not applicableUs
Categories
UNII
4PVP2HCH4T
CAS number
Not Available
Weight
Average: 138.1207
Monoisotopic: 138.031694058
Chemical Formula
C7H6O3
InChI Key
IBGBGRVKPALMCQ-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
IUPAC Name
3,4-dihydroxybenzaldehyde
SMILES
OC1=CC=C(C=O)C=C1O

Pharmacology

Indication
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
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with 4-hydroxycoumarin.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Protocatechualdehyde.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Protocatechualdehyde.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with Acetylsalicylic acid.
AlteplaseThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with Alteplase.
AmediplaseThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with Amediplase.
AnagrelideThe risk or severity of bleeding can be increased when Protocatechualdehyde is combined with Anagrelide.
AncrodThe risk or severity of bleeding can be increased when Ancrod is combined with Protocatechualdehyde.
Food Interactions
Not Available

References

General References
  1. Jeong JB, Lee SH: Protocatechualdehyde possesses anti-cancer activity through downregulating cyclin D1 and HDAC2 in human colorectal cancer cells. Biochem Biophys Res Commun. 2013 Jan 4;430(1):381-6. doi: 10.1016/j.bbrc.2012.11.018. Epub 2012 Nov 14. [PubMed:23159608]
  2. Choi J, Jiang X, Jeong JB, Lee SH: Anticancer activity of protocatechualdehyde in human breast cancer cells. J Med Food. 2014 Aug;17(8):842-8. doi: 10.1089/jmf.2013.0159. Epub 2014 Apr 8. [PubMed:24712725]
External Links
Human Metabolome Database
HMDB0059965
KEGG Compound
C16700
PubChem Compound
8768
PubChem Substance
347827959
ChemSpider
8438
ChEBI
50205
ChEMBL
CHEMBL222021
Wikipedia
Protocatechuic_aldehyde

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical0.032 mL/100mL
EmulsionTopical0.0315 mL/100mL
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
logP0.89ALOGPS
logP1.08ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.6 m3·mol-1ChemAxon
Polarizability12.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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/MSsplash10-000i-0900000000-db13978cfcbc33c6da32
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-ed3a0258f14e4361b25c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-9200000000-cdb54c91531419396213
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-db13978cfcbc33c6da32
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-ed3a0258f14e4361b25c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-9200000000-cdb54c91531419396213
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-882b8375384be94a3491
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-25b2a170eaf9dd74c4a0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kw4-9300000000-e349b638bc98dcdf0ade
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-882b8375384be94a3491
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-25b2a170eaf9dd74c4a0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kw4-9300000000-e349b638bc98dcdf0ade
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-000i-0900000000-aa91c9c469ec39450435
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-000i-0900000000-25b5b2bc87af9df04e91

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Hydroxybenzaldehydes
Alternative Parents
Catechols / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organic oxides / Hydrocarbon derivatives
Substituents
Hydroxybenzaldehyde / Catechol / Benzoyl / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Benzenoid / Monocyclic benzene moiety / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dihydroxybenzaldehyde (CHEBI:50205) / an aryl aldehyde (CPD-7616)

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 07:08