ChemFOnt: Showing chemical card for 5-Methoxysalicylic acid (CFc000001242)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:50 UTC

Chemfont ID

CFc000001242

Molecule Identification

Common Name

5-Methoxysalicylic acid

Definition

5-methoxysalicylic acid is a methoxysalicylic acid that is salicylic acid which is carrying a methoxy group at position 5. It has a role as a bacterial metabolite and a human urinary metabolite. 5-Methoxysalicylic acid is also known as 2-hydroxy-5-methoxybenzoate or 5-methoxy-2-hydroxybenzoate and belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Outside of the human body, 5-Methoxysalicylic acid has been detected, but not quantified in herbs and spices and tea.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-MeOSA	ChEBI
5-Methoxy-2-hydroxybenzoic acid	ChEBI
5-O-Methyl gentisic acid	ChEBI
6-Hydroxy-m-anisic acid	ChEBI
Acid5-methoxysalicylic	ChEBI
5-Methoxy-2-hydroxybenzoate	Generator
5-O-Methyl gentisate	Generator
6-Hydroxy-m-anisate	Generator
5-Methoxysalicylate	Generator
2-Hydroxy-5-methoxybenzoate	HMDB, Generator
2-Hydroxy-5-methoxybenzoic acid	HMDB
6-Methoxy-m-anisate	HMDB
6-Methoxy-m-anisic acid	HMDB
5-Methoxysalicylic acid, sodium salt	MeSH, HMDB
5-Methoxysalicylic acid	MeSH

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2-hydroxy-5-methoxybenzoic acid

Traditional Name

5-methoxysalicylic acid

CAS Registry Number

2612-02-4

SMILES

COC1=CC(C(O)=O)=C(O)C=C1

InChI Identifier

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

InChI Key

IZZIWIAOVZOBLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
4-alkoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001868)

Cell

Red blood cell (HMDB: HMDB0001868)
Erythrocyte (HMDB: HMDB0001868)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Cellular substructure

Cytoplasm (HMDB: HMDB0001868)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001868)

Source

Exogenous

Exogenous (HMDB: HMDB0001868)

Food

Food (HMDB: HMDB0001868)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0001868)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.38 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.82	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.52	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.76 m³·mol⁻¹	ChemAxon
Polarizability	15.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001868

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011959

KNApSAcK ID

C00055625

Chemspider ID

68296

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Methoxysalicylic_acid

METLIN ID

4164

PubChem Compound

75787

PDB ID

Not Available

ChEBI ID

89830

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Nagasawa, Masaaki; Nishioka, Hiroyasu; Suzuki, Takanori; Nagano, Eiichi; Ishii, Katsuyuki; Nakao, Ryu. Preparation of salicylic acids from 2-methoxybenzoic acids. Jpn. Kokai Tokkyo Koho (2000), 6 pp.

Showing chemical card for 5-Methoxysalicylic acid (CFc000001242)

MOL for CFc000001242 (5-Methoxysalicylic acid)

3D MOL for CFc000001242 (5-Methoxysalicylic acid)

3D SDF for CFc000001242 (5-Methoxysalicylic acid)

3D-SDF for CFc000001242 (5-Methoxysalicylic acid)

PDB for CFc000001242 (5-Methoxysalicylic acid)

3D PDB for CFc000001242 (5-Methoxysalicylic acid)

SMILES for CFc000001242 (5-Methoxysalicylic acid)

INCHI for CFc000001242 (5-Methoxysalicylic acid)

Structure for CFc000001242 (5-Methoxysalicylic acid)

3D Structure for CFc000001242 (5-Methoxysalicylic acid)