Protocatechualdehyde

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

Identification

Generic Name
Protocatechualdehyde
DrugBank Accession Number
DB11268
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 138.1207
Monoisotopic: 138.031694058
Chemical Formula
C7H6O3
Synonyms
  • 3,4-dihydroxybenzaldehyde
  • Protocatechuic aldehyde
  • Rancinamycin IV
External IDs
  • NSC-22961

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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.
DrugInteraction
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.
AlteplaseThe risk or severity of bleeding can be increased when Alteplase is combined with Protocatechualdehyde.
AncrodThe risk or severity of bleeding can be increased when Ancrod is combined with Protocatechualdehyde.
AnistreplaseThe risk or severity of bleeding can be increased when Anistreplase is combined with Protocatechualdehyde.
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
O Hui White Extreme CellightCream0.032 mL/100mLTopicalLg Household & Health Care Ltd.2011-03-16Not applicableUS flag
O Hui White Extreme CellightEmulsion0.0315 mL/100mLTopicalLg Household & Health Care Ltd.2011-03-07Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
O Hui White Extreme CellightProtocatechualdehyde (0.032 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-03-16Not applicableUS flag
O Hui White Extreme CellightProtocatechualdehyde (0.0315 mL/100mL)EmulsionTopicalLg Household & Health Care Ltd.2011-03-07Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Benzoyl / Catechol / Hydrocarbon derivative / Hydroxybenzaldehyde / Monocyclic benzene moiety / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dihydroxybenzaldehyde (CHEBI:50205) / an aryl aldehyde (CPD-7616)
Affected organisms
Not Available

Chemical Identifiers

UNII
4PVP2HCH4T
CAS number
139-85-5
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
[H]C(=O)C1=CC(O)=C(O)C=C1

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0059965
KEGG Compound
C16700
PubChem Compound
8768
PubChem Substance
347827959
ChemSpider
8438
BindingDB
50192743
RxNav
1362689
ChEBI
50205
ChEMBL
CHEMBL222021
ZINC
ZINC000000013245
PDBe Ligand
H6N
Wikipedia
Protocatechuic_aldehyde
PDB Entries
6i73

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-052r-2900000000-fd0d28650a72226166e6
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0002-0040900010-522c055741661bbc5ba8
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0002-0040900010-522c055741661bbc5ba8
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-0002-0040900010-522c055741661bbc5ba8
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-002r-0905000000-7987816fb8648b0eea18
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-000i-0900000000-aa91c9c469ec39450435
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-000i-0900000000-25b5b2bc87af9df04e91
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSsplash10-000i-0900000000-03d9e2dbe57c9bcfb9ab
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-002r-0905000000-7987816fb8648b0eea18
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-6900000000-8e4ec04e40d3e275961b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-f9ca1cbaf9235226deaa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9200000000-eb3f6947a19d092312c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-8900000000-55a3d62374c7a8136e4e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gbc-9000000000-0d6de1e72018bfc09fa6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uy0-9000000000-b7e3f218b00222914021
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]-127.8288905
predicted
DarkChem Lite v0.1.0
[M-H]-127.7906905
predicted
DarkChem Lite v0.1.0
[M-H]-127.7310905
predicted
DarkChem Lite v0.1.0
[M-H]-127.13828
predicted
DeepCCS 1.0 (2019)
[M+H]+129.5870905
predicted
DarkChem Lite v0.1.0
[M+H]+129.0078905
predicted
DarkChem Lite v0.1.0
[M+H]+128.6131905
predicted
DarkChem Lite v0.1.0
[M+H]+129.5129
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.1054905
predicted
DarkChem Lite v0.1.0
[M+Na]+127.7565905
predicted
DarkChem Lite v0.1.0
[M+Na]+128.0064905
predicted
DarkChem Lite v0.1.0
[M+Na]+138.24394
predicted
DeepCCS 1.0 (2019)

Drug created at December 03, 2015 16:51 / Updated at July 11, 2020 03:43