MiMeDB: Showing metabocard for orsellinate (MMDBc0056237)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:20:23 UTC

Update Date

2025-10-07 16:09:40 UTC

Metabolite ID

MMDBc0056237

Metabolite Identification

Common Name

orsellinate

Description

Orsellinate is a polyphenolic compound belonging to the class of aromatic metabolites. Its chemical structure features a substituted aromatic ring, which plays a crucial role in its chemical reactivity and interactions. In biological pathways, orsellinate is involved in various biosynthetic processes, including the formation of thioesters and subsequent modifications such as O-methylation and iodination. For instance, studies have shown that the formation of the orsellinate thioester is followed by sequential C-2 O-methylation, C-5 iodination, and C-3 oxidation, highlighting its complex metabolic transformations (PMID:40540714 ). Additionally, multi-omics analyses suggest that specific polyketide synthases, such as PpPKS1, are likely involved in the biosynthesis of ethyl orsellinate, while other enzymes contribute to the synthesis of related compounds like 6-methylsalicylic acid (PMID:4027 ...). Furthermore, orsellinate and its derivatives have been noted for their efficacy in absorbing radiation beyond 1500 nm, particularly in sunscreens, where less-substituted aromatic compounds like methyl orsellinate exhibit superior performance compared to more substituted variants (PMID:40599062 ).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4    5                                                       
CONECT    3    5    6                                                       
CONECT    4    1    2    7                                                  
CONECT    5    2    3    9                                                  
CONECT    6    3    7   10                                                  
CONECT    7    4    6    8                                                  
CONECT    8    7   11   12                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
Orsellinate	ChEBI
Orsellinic acid	Generator
O-Orsellinic acid	Generator

Molecular Formula

C₈H₇O₄

Average Mass

167.141

Monoisotopic Mass

167.034982285

IUPAC Name

4-carboxy-3-hydroxy-5-methylbenzen-1-olate

Traditional Name

4-carboxy-3-hydroxy-5-methylbenzenolate

CAS Registry Number

Not Available

SMILES

CC1=CC([O-])=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)/p-1

InChI Key

AMKYESDOVDKZKV-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives 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

Substituents

Hydroxybenzoic acid
Benzoic acid
Benzoyl
M-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Phenoxide
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydroxybenzoate (CHEBI:16162 )
a small molecule (CPD-47 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.19	ChemAxon
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.87 m³·mol⁻¹	ChemAxon
Polarizability	15.39 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

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

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

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	Basidiomycota	1
Eukaryota/Fungi	Ascomycota	5

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

4573900

KEGG Compound ID

Not Available

BioCyc ID

CPD-47

BiGG ID

Not Available

Wikipedia Link

Orsellinic acid

METLIN ID

Not Available

PubChem Compound

5460334

PDB ID

Not Available

ChEBI ID

16162

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for orsellinate (MMDBc0056237)

MOL for #<Metabolite:0x00007fade0d76438>

3D MOL for #<Metabolite:0x00007fade0d76438>

3D SDF for #<Metabolite:0x00007fade0d76438>

3D-SDF for #<Metabolite:0x00007fade0d76438>

PDB for #<Metabolite:0x00007fade0d76438>

3D PDB for #<Metabolite:0x00007fade0d76438>

SMILES for #<Metabolite:0x00007fade0d76438>

INCHI for #<Metabolite:0x00007fade0d76438>

Structure for #<Metabolite:0x00007fade0d76438>

3D Structure for #<Metabolite:0x00007fade0d76438>