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Record Information
Version2.0
Created at2021-01-05 20:36:25 UTC
Updated at2021-07-15 17:06:58 UTC
NP-MRD IDNP0010749
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylorsellinic acid
Provided ByNPAtlasNPAtlas Logo
Description2,4-Dihydroxy-3,6-dimethylbenzoic acid is also known as 3,6-dimethyl-2,4-dihydroxybenzoic acid or beta-orcinolcarboxylic acid. 2,4-Dihydroxy-3,6-dimethylbenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-Methylorsellinic acid is found in Aspergillus nidulans, Aspergillus silvaticus, Cladonia rangiferina, Dolichousnea longissima and Ricinodendron heudelotii. 3-Methylorsellinic acid was first documented in 1975 (PMID: 1155879). Based on a literature review a small amount of articles have been published on 2,4-dihydroxy-3,6-dimethylbenzoic acid (PMID: 15307685) (PMID: 28029061).
Structure
Thumb
Synonyms
ValueSource
3,6-Dimethyl-2,4-dihydroxybenzoic acidChEBI
beta-Orcinolcarboxylic acidChEBI
3,6-Dimethyl-2,4-dihydroxybenzoateGenerator
b-OrcinolcarboxylateGenerator
b-Orcinolcarboxylic acidGenerator
beta-OrcinolcarboxylateGenerator
Β-orcinolcarboxylateGenerator
Β-orcinolcarboxylic acidGenerator
2,4-Dihydroxy-3,6-dimethylbenzoateGenerator
3-MethylorsellinateGenerator
Chemical FormulaC9H10O4
Average Mass182.1750 Da
Monoisotopic Mass182.05791 Da
IUPAC Name2,4-dihydroxy-3,6-dimethylbenzoic acid
Traditional Name2,4-dihydroxy-3,6-dimethylbenzoic acid
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=C(C)C(O)=C1C(O)=O
InChI Identifier
InChI=1S/C9H10O4/c1-4-3-6(10)5(2)8(11)7(4)9(12)13/h3,10-11H,1-2H3,(H,12,13)
InChI KeyVHNLJRRECIZZPX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus nidulansNPAtlas
Aspergillus silvaticusLOTUS Database
Cladonia rangiferinaLOTUS Database
Dolichousnea longissimaLOTUS Database
Ricinodendron heudelotiiLOTUS Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid
  • P-xylenol
  • Xylenol
  • Benzoyl
  • M-cresol
  • O-cresol
  • Resorcinol
  • P-xylene
  • Xylene
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.54ALOGPS
logP2.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.36 m³·mol⁻¹ChemAxon
Polarizability17.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA017203
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID643358
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound736228
PDB IDNot Available
ChEBI ID146309
Good Scents IDNot Available
References
General References
  1. Verachtert H, Hanssens L: Isolation and identification of phenolic substances from the fungus Penicillium spinulosum. Ann Microbiol (Paris). 1975 Feb-Mar;126(2):143-9. [PubMed:1155879 ]
  2. Yunmei B, Lei B, Wei B, Yanling F: [Studies on antibacterial activities of secondary metabolites from fungus Cephalosporium sp. AL031]. Zhong Yao Cai. 2004 Apr;27(4):270-2. [PubMed:15307685 ]
  3. Zrnzevic I, Jovanovic O, Zlatanovic I, Stojanovic I, Petrovic G, Stojanovic G: Constituents of Ramalina capitata (Ach.) Nyl. extracts. Nat Prod Res. 2017 Apr;31(7):857-860. doi: 10.1080/14786419.2016.1272112. Epub 2016 Dec 28. [PubMed:28029061 ]