MiMeDB: Showing metabocard for 3,4-dihydroxybenzaldehyde (MMDBc0054246)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:01:22 UTC

Update Date

2024-04-30 20:52:09 UTC

Metabolite ID

MMDBc0054246

Metabolite Identification

Common Name

3,4-dihydroxybenzaldehyde

Description

3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
1,2-Dihydroxy-4-formylbenzene	ChEBI
3,4-Dihydroxybenzenecarbonal	ChEBI
4-Formyl-1,2-benzenediol	ChEBI
4-Formyl-1,2-dihydroxybenzene	ChEBI
Protocatechualdehyde	ChEBI
Protocatechuic aldehyde	ChEBI
Protocatechualdehyde, 3H-labeled	MeSH
Rancinamycin IV	MeSH
Protocatechualdehyde, formyl-14C-labeled	MeSH
3,4-Dihydroxybenzaldehyde	HMDB

Molecular Formula

C₇H₆O₃

Average Mass

138.1207

Monoisotopic Mass

138.031694058

IUPAC Name

3,4-dihydroxybenzaldehyde

Traditional Name

3,4-dihydroxybenzaldehyde

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=O)C=C1O

InChI Identifier

InChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H

InChI Key

IBGBGRVKPALMCQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Hydroxybenzaldehyde
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzaldehyde (CHEBI:50205 )
an aryl aldehyde (CPD-7616 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	14.3 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.08	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.6 m³·mol⁻¹	ChemAxon
Polarizability	12.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-2900000000-fd0d28650a72226166e6	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00yi-8690000000-16ccc54dcf22361cffb1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0002-0040900010-522c055741661bbc5ba8	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-002r-0905000000-7987816fb8648b0eea18	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-aa91c9c469ec39450435	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0900000000-25b5b2bc87af9df04e91	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0900000000-03d9e2dbe57c9bcfb9ab	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-002r-0905000000-7987816fb8648b0eea18	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0900000000-aa91c9c469ec39450435	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0900000000-25b5b2bc87af9df04e91	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-aa91c9c469ec39450435	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-25b5b2bc87af9df04e91	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-db13978cfcbc33c6da32	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-ed3a0258f14e4361b25c	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9200000000-cdb54c91531419396213	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-db13978cfcbc33c6da32	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-ed3a0258f14e4361b25c	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9200000000-cdb54c91531419396213	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-882b8375384be94a3491	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-25b2a170eaf9dd74c4a0	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kw4-9300000000-e349b638bc98dcdf0ade	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-882b8375384be94a3491	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1900000000-25b2a170eaf9dd74c4a0	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kw4-9300000000-e349b638bc98dcdf0ade	2015-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015490	(E)-caffeoyl-CoA	3,4-dihydroxybenzaldehyde	Hydroxycinnamoyl-CoA hydratase-lyase	Hydration/dehydration of C-O bond	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	1	Human ; Human subgingival plaque
Eukaryota/Fungi	Basidiomycota	2
Bacteria	Actinobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	3.577	0.566	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	19812218
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0059965

DrugBank ID

DB11268

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Protocatechuic aldehyde

METLIN ID

Not Available

PubChem Compound

8768

PDB ID

Not Available

ChEBI ID

50205

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]

Showing metabocard for 3,4-dihydroxybenzaldehyde (MMDBc0054246)

MOL for #<Metabolite:0x000055c79c643c50>

3D MOL for #<Metabolite:0x000055c79c643c50>

3D SDF for #<Metabolite:0x000055c79c643c50>

3D-SDF for #<Metabolite:0x000055c79c643c50>

PDB for #<Metabolite:0x000055c79c643c50>

3D PDB for #<Metabolite:0x000055c79c643c50>

SMILES for #<Metabolite:0x000055c79c643c50>

INCHI for #<Metabolite:0x000055c79c643c50>

Structure for #<Metabolite:0x000055c79c643c50>

3D Structure for #<Metabolite:0x000055c79c643c50>