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Record Information
Version2.0
Created at2021-01-05 20:36:19 UTC
Updated at2021-07-15 17:06:57 UTC
NP-MRD IDNP0010746
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde
Provided ByNPAtlasNPAtlas Logo
Description2,4-Dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde, also known as 3-(2-formyl-3,5-dihydroxy-4-methylphenyl)-2-propanone or DHMBA, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 2,4-Dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde 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. 2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde is found in Aspergillus nidulans. 2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde was first documented in 2012 (PMID: 23001671). Based on a literature review a small amount of articles have been published on 2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde.
Structure
Thumb
Synonyms
ValueSource
3-(2-Formyl-3,5-dihydroxy-4-methylphenyl)-2-propanoneChEBI
DHMBAChEBI
Chemical FormulaC11H12O4
Average Mass208.2130 Da
Monoisotopic Mass208.07356 Da
IUPAC Name2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde
Traditional Name2,4-dihydroxy-3-methyl-6-(2-oxopropyl)benzaldehyde
CAS Registry NumberNot Available
SMILES
CC(=O)CC1=CC(O)=C(C)C(O)=C1C=O
InChI Identifier
InChI=1S/C11H12O4/c1-6(13)3-8-4-10(14)7(2)11(15)9(8)5-12/h4-5,14-15H,3H2,1-2H3
InChI KeyNYFZWIIIOFTTKN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus nidulansNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Phenylpropane
  • Hydroxybenzaldehyde
  • Benzoyl
  • O-cresol
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Toluene
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • 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
logP1.34ALOGPS
logP2.21ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.74ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.5 m³·mol⁻¹ChemAxon
Polarizability21.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA007909
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9270962
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11095820
PDB IDNot Available
ChEBI ID155860
Good Scents IDNot Available
References
General References
  1. Gerke J, Bayram O, Feussner K, Landesfeind M, Shelest E, Feussner I, Braus GH: Breaking the silence: protein stabilization uncovers silenced biosynthetic gene clusters in the fungus Aspergillus nidulans. Appl Environ Microbiol. 2012 Dec;78(23):8234-44. doi: 10.1128/AEM.01808-12. Epub 2012 Sep 21. [PubMed:23001671 ]