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Record Information
Version2.0
Created at2022-04-28 22:46:56 UTC
Updated at2025-02-11 15:48:26 UTC
NP-MRD IDNP0077652
Natural Product DOIhttps://doi.org/10.57994/2826
Secondary Accession NumbersNone
Natural Product Identification
Common NameKojic acid
DescriptionKojic acid, also known as acido kojico or kojisaeure, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Kojic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Kojic acid is found in Aspergillus oryzae, Aspergillus terricola, Glycine max , Marrubium cylleneum and Taxus mairei . Kojic acid was first documented in 1999 (PMID: 10466431). Kojic acid is a potentially toxic compound (PMID: 11534762) (PMID: 16198580).
Structure
Thumb
Synonyms
ValueSource
5-Hydroxy-2-(hydroxymethyl)-4-pyroneChEBI
5-Hydroxy-2-hydroxymethyl-4-pyroneChEBI
Acido kojicoChEBI
KojisaeureChEBI
KojateGenerator
2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-oneHMDB
2-Hydroxymethyl-5-hydroxy-gamma-pyroneHMDB
5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-oneHMDB
5-Hydroxy-2-(hydroxymethyl)pyran-4-oneHMDB
5-Hydroxy-2-hydroxymethyl-4H-4-pyranoneHMDB
KOJHMDB
Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)HMDB
Kojyl-appaHMDB
5-((3-Aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4H-pyran-4-oneHMDB
Chemical FormulaC6H6O4
Average Mass142.1094 Da
Monoisotopic Mass142.02661 Da
IUPAC Name5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
Traditional Namekojic acid
CAS Registry NumberNot Available
SMILES
OCC1=CC(=O)C(O)=CO1
InChI Identifier
InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
InChI KeyBEJNERDRQOWKJM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Predicted Spectra
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Aspergillus oryzaeLOTUS Database
Aspergillus terricolaLOTUS Database
Glycine maxPlant
Marrubium cylleneumLOTUS Database
Taxus maireiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Cyclic ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
logP-1ALOGPS
logP-0.5ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.27 m³·mol⁻¹ChemAxon
Polarizability12.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032923
DrugBank IDDB01759
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010906
KNApSAcK IDC00041026
Chemspider ID3708
KEGG Compound IDC14516
BioCyc IDKOJIC-ACID
BiGG IDNot Available
Wikipedia LinkKojic_acid
METLIN IDNot Available
PubChem Compound3840
PDB IDKOJ
ChEBI ID43572
Good Scents IDNot Available
References
General References
  1. Novotny L, Rauko P, Abdel-Hamid M, Vachalkova A: Kojic acid--a new leading molecule for a preparation of compounds with an anti-neoplastic potential. Neoplasma. 1999;46(2):89-92. [PubMed:10466431 ]
  2. Moon KY, Ahn KS, Lee J, Kim YS: Kojic acid, a potential inhibitor of NF-kappaB activation in transfectant human HaCaT and SCC-13 cells. Arch Pharm Res. 2001 Aug;24(4):307-11. doi: 10.1007/BF02975097. [PubMed:11534762 ]
  3. Khan KM, Maharvi GM, Khan MT, Jabbar Shaikh A, Perveen S, Begum S, Choudhary MI: Tetraketones: a new class of tyrosinase inhibitors. Bioorg Med Chem. 2006 Jan 15;14(2):344-51. doi: 10.1016/j.bmc.2005.08.029. Epub 2005 Sep 28. [PubMed:16198580 ]