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Record Information
Version1.0
Created at2006-02-23 11:14:42 UTC
Updated at2023-06-08 20:02:08 UTC
NP-MRD IDNP0000067
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methoxysalicylic acid
Description5-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
Thumb
Synonyms
ValueSource
5-MeOSAChEBI
5-Methoxy-2-hydroxybenzoic acidChEBI
5-O-Methyl gentisic acidChEBI
6-Hydroxy-m-anisic acidChEBI
Acid5-methoxysalicylicChEBI
5-Methoxy-2-hydroxybenzoateGenerator
5-O-Methyl gentisateGenerator
6-Hydroxy-m-anisateGenerator
5-MethoxysalicylateGenerator
2-Hydroxy-5-methoxybenzoateHMDB
2-Hydroxy-5-methoxybenzoic acidHMDB
6-Methoxy-m-anisateHMDB
6-Methoxy-m-anisic acidHMDB
5-Methoxysalicylic acid, sodium saltHMDB
5-Methoxysalicylic acidMeSH
Chemical FormulaC8H8O4
Average Mass168.1467 Da
Monoisotopic Mass168.04226 Da
IUPAC Name2-hydroxy-5-methoxybenzoic acid
Traditional Name5-methoxysalicylic acid
CAS Registry Number2612-02-4
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 KeyIZZIWIAOVZOBLF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-10-09View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-10-09View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-10-09View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-10-09View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-10-09View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-08View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Conyza bonariensisLOTUS Database
Epehdra sinica-
Primula verisKNApSAcK Database
Thalictrum fargesiiLOTUS Database
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 146 °CNot Available
Boiling Point347.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9 mg/mLNot Available
LogP2.100 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility3.38 g/LALOGPS
logP1.85ALOGPS
logP1.82ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001868
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011959
KNApSAcK IDC00055625
Chemspider ID68296
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Methoxysalicylic_acid
METLIN ID4164
PubChem Compound75787
PDB IDNot Available
ChEBI ID89830
Good Scents IDrw1210831
References
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 ]
  2. Nishihata T, Higuchi T, Kamada A: Salicylate-promoted permeation of cefoxitin, insulin and phenylalanine across red cell membrane. Possible mechanism. Life Sci. 1984 Jan 30;34(5):437-45. [PubMed:6319944 ]
  3. Alanis-Sanchez BM, Perez-Tapia SM, Vazquez-Leyva S, Mejia-Calvo I, Macias-Palacios Z, Vallejo-Castillo L, Flores-Ortiz CM, Guerrero-Barajas C, Cruz-Maya JA, Jan-Roblero J: Utilization of naproxen by Amycolatopsis sp. Poz 14 and detection of the enzymes involved in the degradation metabolic pathway. World J Microbiol Biotechnol. 2019 Nov 14;35(12):186. doi: 10.1007/s11274-019-2764-0. [PubMed:31728655 ]
  4. Lee C, Ni CK: Soft Matrix-Assisted Laser Desorption/Ionization for Labile Glycoconjugates. J Am Soc Mass Spectrom. 2019 Aug;30(8):1455-1463. doi: 10.1007/s13361-019-02208-4. Epub 2019 Apr 16. [PubMed:30993639 ]
  5. Lee D, Cha S: 5-Methoxysalicylic acid matrix for ganglioside analysis with matrix-assisted laser desorption/ionization mass spectrometry. J Am Soc Mass Spectrom. 2015 Mar;26(3):522-5. doi: 10.1007/s13361-014-1037-2. Epub 2014 Dec 11. [PubMed:25503079 ]
  6. Yasuda A, Ishimaru T, Nishihara S, Sakai M, Kawasaki H, Arakawa R, Shigeri Y: A thiophene-containing compound as a matrix for matrix-assisted laser desorption/ ionization mass spectrometry and the electrical conductivity of matrix crystals. Eur J Mass Spectrom (Chichester). 2013;19(1):29-37. doi: 10.1255/ejms.1215. [PubMed:23841223 ]
  7. Ostertag LM, O'Kennedy N, Horgan GW, Kroon PA, Duthie GG, de Roos B: In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations. Mol Nutr Food Res. 2011 Nov;55(11):1624-36. doi: 10.1002/mnfr.201100135. Epub 2011 Sep 5. [PubMed:21898791 ]
  8. Gunes E, Parlak C: DFT, FT-Raman and FT-IR investigations of 5-methoxysalicylic acid. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Nov;82(1):504-12. doi: 10.1016/j.saa.2011.07.089. Epub 2011 Aug 4. [PubMed:21840249 ]
  9. Tsubery H, Mrksich M: Biochemical assays of immobilized oligonucleotides with mass spectrometry. Langmuir. 2008 May 20;24(10):5433-8. doi: 10.1021/la7040482. Epub 2008 Apr 12. [PubMed:18407676 ]
  10. Abou El-Nasr EA, Fujii A, Yahagi T, Ebata T, Mikami N: Laser spectroscopic investigation of salicylic acids hydrogen bonded with water in supersonic jets: Microsolvation effects for excited state proton dislocation. J Phys Chem A. 2005 Mar 24;109(11):2498-504. doi: 10.1021/jp046381a. [PubMed:16833551 ]
  11. Smoluch M, Joshi H, Gerssen A, Gooijer C, van der Zwan G: Fast excited-state intramolecular proton transfer and subnanosecond dynamic stokes shift of time-resolved fluorescence spectra of the 5-methoxysalicylic acid/diethyl ether complex. J Phys Chem A. 2005 Feb 3;109(4):535-41. doi: 10.1021/jp0475281. [PubMed:16833377 ]