MiMeDB: Showing metabocard for Orsellinaldehyde (MMDBc0017428)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:48:52 UTC

Update Date

2025-10-07 16:06:41 UTC

Metabolite ID

MMDBc0017428

Metabolite Identification

Common Name

Orsellinaldehyde

Description

Orsellinaldehyde is a natural product belonging to the class of aromatic aldehydes, specifically characterized as 2,4-dihydroxy-6-methylbenzaldehyde. Its chemical structure features a benzene ring with hydroxyl groups and a methyl group, contributing to its biological activity. In the realm of fungal metabolism, orsellinaldehyde has been implicated in various biosynthetic pathways, notably in the production of triorsellinaldehyde, a novel secondary metabolite derived from a polyketide synthase gene in Aspergillus nidulans (PMID:39334518 ). Interestingly, the deletion of this gene did not halt triorsellinaldehyde production, suggesting alternative biosynthetic routes may exist (PMID:39334518 ). Furthermore, orsellinaldehyde has demonstrated significant antifungal properties, effectively suppressing anthracnose disease in fruits such as mango and cucumber by inhibiting pathogenic fungi (PMID:38802124 ). Its broad-spectrum inhibitory activity against different plant pathogenic fungi highlights its potential utility as a natural fungicide (PMID:38802124 ). The identification of orsellinaldehyde as a potent antifungal compound from mushroom culture filtrates underscores its relevance in agricultural applications for disease management (PMID:38802124 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Orsellinaldehyde	MeSH

Molecular Formula

C₈H₈O₃

Average Mass

152.149

Monoisotopic Mass

152.047344118

IUPAC Name

2,4-dihydroxy-6-methylbenzaldehyde

Traditional Name

2,4-dihydroxy-6-methylbenzaldehyde

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C=O

InChI Identifier

InChI=1S/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3

InChI Key

LJFQTUKKYWDRAT-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
Resorcinol
M-cresol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	8.14 g/L	ALOGPS
logP	1.12	ALOGPS
logP	2.24	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-5.7	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	41.64 m³·mol⁻¹	ChemAxon
Polarizability	14.85 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 (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	86.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	38.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	338.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	598.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	534.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	385.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1417.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	103.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	574.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	315.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	278.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	251.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	128.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	211.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	545.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	187.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	435.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1182.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	934.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Orsellinaldehyde_TMS_1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C=O	standard non polar	2025-10-23	1390.4
Gas Chromatography	Orsellinaldehyde_TMS_2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C=O	standard non polar	2025-10-23	2118.06
Gas Chromatography	Orsellinaldehyde_TMS_3	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C=O	standard non polar	2025-10-23	1611.25
Gas Chromatography	Orsellinaldehyde_TMS_1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C=O	standard polar	2025-10-23	1552.93
Gas Chromatography	Orsellinaldehyde_TMS_2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C=O	standard polar	2025-10-23	1666.2
Gas Chromatography	Orsellinaldehyde_TMS_3	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C=O	standard polar	2025-10-23	1855.7

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0025862	Malonyl-CoA	Orsellinaldehyde	Non-reducing polyketide synthase pkfA	Synthesis	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	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

251690

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Orsellinaldehyde (MMDBc0017428)

MOL for #<Metabolite:0x00007f9acaab9a48>

3D MOL for #<Metabolite:0x00007f9acaab9a48>

3D SDF for #<Metabolite:0x00007f9acaab9a48>

3D-SDF for #<Metabolite:0x00007f9acaab9a48>

PDB for #<Metabolite:0x00007f9acaab9a48>

3D PDB for #<Metabolite:0x00007f9acaab9a48>

SMILES for #<Metabolite:0x00007f9acaab9a48>

INCHI for #<Metabolite:0x00007f9acaab9a48>

Structure for #<Metabolite:0x00007f9acaab9a48>

3D Structure for #<Metabolite:0x00007f9acaab9a48>