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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Methoxysalicylic acid (HMDB01868)

Record Information
Version 3.5
Creation Date 2006-02-23 04:14:42 -0700
Update Date 2013-02-08 17:10:54 -0700
HMDB ID HMDB01868
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Methoxysalicylic acid
Description 5-Methoxysalicylic acid is an aminosalicylic acid that has been found to. enhance intestinal absorption of insulin in rats and insulin uptake into human red blood cells (PMID 6319944 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Hydroxy-5-methoxybenzoate
  2. 2-Hydroxy-5-methoxybenzoic acid
  3. 5-Methoxy-2-hydroxybenzoate
  4. 5-Methoxy-2-hydroxybenzoic acid
  5. 5-Methoxysalicylate
  6. 5-Methoxysalicylic acid
  7. 6-Hydroxy-m-Anisate
  8. 6-Hydroxy-m-Anisic acid
  9. 6-Methoxy-m-anisate
  10. 6-Methoxy-m-anisic acid
Chemical Formula C8H8O4
Average Molecular Weight 168.1467
Monoisotopic Molecular Weight 168.042258744
IUPAC Name 2-hydroxy-5-methoxybenzoic acid
Traditional IUPAC Name 2-hydroxy-5-methoxybenzoic 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
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Hydroxybenzoic Acid Derivatives
Other Descriptors
  • Benzoic Acid and Derivatives
  • Methoxyphenols and Derivatives
  • Organic Compounds
  • Salicylic Acid and Derivatives
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Benzoyl
  • Carboxylic Acid
  • Phenol
  • Phenol Derivative
Direct Parent Hydroxybenzoic Acid Derivatives
Ontology
Status Detected and Quantified
Origin
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 142 - 146 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 9 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.38 g/L ALOGPS
LogP 1.85 ALOGPS
LogP 1.82 ChemAxon
LogS -1.70 ALOGPS
pKa (strongest acidic) 2.52 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 41.76 ChemAxon
Polarizability 15.8 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum MALDI-TOF (Voyager DE-PRO, Applied Biosystems)
MS/MS Spectrum MALDI-TOF (Voyager DE-PRO, Applied Biosystems)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Red Blood Cell
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.14 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011959
KNApSAcK ID Not Available
Chemspider ID 68296 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01868 Link_out
Metagene Link HMDB01868 Link_out
METLIN ID 4164 Link_out
PubChem Compound 75787 Link_out
PDB ID Not Available
ChEBI ID 545920 Link_out
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.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Nishihata T, Higuchi T, Kamada A: Possible mechanism of uptake for several compounds in ionized form through human erythrocyte membrane. Life Sci. 1984 Jan 30;34(5):427-36. Pubmed: 6694531 Link_out