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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:41 UTC

Update Date

2023-02-21 17:22:47 UTC

HMDB ID

HMDB0032923

Secondary Accession Numbers

HMDB32923

Metabolite Identification

Common Name

Kojic acid

Description

Kojic 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 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. Based on a literature review a significant number of articles have been published on Kojic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-2-(hydroxymethyl)-4-pyrone	ChEBI
5-Hydroxy-2-hydroxymethyl-4-pyrone	ChEBI
Acido kojico	ChEBI
Kojisaeure	ChEBI
Kojate	Generator
2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one	HMDB
2-Hydroxymethyl-5-hydroxy-gamma-pyrone	HMDB
5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one	HMDB
5-Hydroxy-2-(hydroxymethyl)pyran-4-one	HMDB
5-Hydroxy-2-hydroxymethyl-4H-4-pyranone	HMDB
KOJ	HMDB
Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)	HMDB
Kojyl-appa	MeSH, HMDB
5-((3-Aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4H-pyran-4-one	MeSH, HMDB

Chemical Formula

C₆H₆O₄

Average Molecular Weight

142.1094

Monoisotopic Molecular Weight

142.02660868

IUPAC Name

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Traditional Name

kojic acid

CAS Registry Number

501-30-4

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 Key

BEJNERDRQOWKJM-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

primary alcohol (CHEBI:43572 )
pyranone (CHEBI:43572 )
enol (CHEBI:43572 )

Ontology

Physiological effect

Health effect

Endocrine system disorder

Thyroidal or parathyroidal disorder

Thyroid cancer (HMDB: HMDB0032923)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032923)
Cytoplasm (HMDB: HMDB0032923)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0032923)
Inhalation (HMDB: HMDB0032923)

Enteral

Ingestion (HMDB: HMDB0032923)

Source

Exogenous

Food

Food (HMDB: HMDB0032923)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0032923)

Endogenous

Fungi

Aspergillus (HMDB: HMDB0032923)

Process

Not Available

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0032923)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0032923)

Biological role

Nutrient (HMDB: HMDB0032923)
Aspergillus metabolite (HMDB: HMDB0032923)

Modulator

Inhibitor

NF-kappaB inhibitor (HMDB: HMDB0032923)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 °C	Not Available
Boiling Point	401.67 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	934600 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.64	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	121.87	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001135

Predicted Molecular Properties

Property	Value	Source
Water Solubility	92.3 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.5	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.27 m³·mol⁻¹	ChemAxon
Polarizability	12.63 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.046	31661259
DarkChem	[M-H]-	126.443	31661259
DeepCCS	[M+H]+	128.852	30932474
DeepCCS	[M-H]-	125.6	30932474
DeepCCS	[M-2H]-	162.814	30932474
DeepCCS	[M+Na]+	137.743	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.5	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	125.0	32859911
AllCCS	[M+Na-2H]-	126.6	32859911
AllCCS	[M+HCOO]-	128.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kojic acid	OCC1=CC(=O)C(O)=CO1	2239.5	Standard polar	33892256
Kojic acid	OCC1=CC(=O)C(O)=CO1	1279.0	Standard non polar	33892256
Kojic acid	OCC1=CC(=O)C(O)=CO1	1408.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kojic acid,1TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O)=CO1	1626.1	Semi standard non polar	33892256
Kojic acid,1TMS,isomer #2	C[Si](C)(C)OC1=COC(CO)=CC1=O	1610.8	Semi standard non polar	33892256
Kojic acid,2TMS,isomer #1	C[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C)=CO1	1695.4	Semi standard non polar	33892256
Kojic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O)=CO1	1852.8	Semi standard non polar	33892256
Kojic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=COC(CO)=CC1=O	1874.0	Semi standard non polar	33892256
Kojic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(=O)C(O[Si](C)(C)C(C)(C)C)=CO1	2164.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Kojic acid GC-MS (2 TMS)	splash10-00di-3950000000-d1e6f5b2e47ac5626c5f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kojic acid EI-B (Non-derivatized)	splash10-05p6-9300000000-704def65872ec878b268	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kojic acid EI-B (Non-derivatized)	splash10-00ko-9500000000-8c8ed21581e5ce62d657	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kojic acid EI-B (Non-derivatized)	splash10-00dj-0972200000-d2e1134bffb7759fab36	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kojic acid GC-EI-TOF (Non-derivatized)	splash10-00dj-1940000000-7a8f18adc19d5275d098	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Kojic acid GC-MS (Non-derivatized)	splash10-00di-3950000000-d1e6f5b2e47ac5626c5f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kojic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03kc-6900000000-d96f98a42148a6e47233	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kojic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9650000000-945de47e75f8ec9b9eaf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kojic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9400000000-15508d600420b309e528	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kojic acid LC-ESI-QTOF , negative-QTOF	splash10-0006-0900000000-7497f496112e599fe169	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kojic acid Linear Ion Trap , negative-QTOF	splash10-001i-9200000000-79391fb0052779fa15a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kojic acid 10V, Negative-QTOF	splash10-0006-0900000000-7497f496112e599fe169	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 10V, Positive-QTOF	splash10-0006-0900000000-b4f5c76df606bee2639b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 20V, Positive-QTOF	splash10-0006-1900000000-8c591424fe1f23b4f463	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 40V, Positive-QTOF	splash10-0a6r-9300000000-2f1a2b3413e8f032697f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 10V, Negative-QTOF	splash10-0006-0900000000-a3e3f8a5e8ce22a6cba3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 20V, Negative-QTOF	splash10-01ox-2900000000-4f881cf1625489e94838	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 40V, Negative-QTOF	splash10-052f-9000000000-82a828b03c7d45e6515f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 10V, Positive-QTOF	splash10-004l-1900000000-9f54abebd3fd9066985d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 20V, Positive-QTOF	splash10-00ov-9600000000-4e5e43090310b4854d93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 40V, Positive-QTOF	splash10-0006-9100000000-20c19898fd61a4ca36ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 10V, Negative-QTOF	splash10-0006-0900000000-781e0069db86c3955b89	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 20V, Negative-QTOF	splash10-0006-9400000000-c6bf0fd6d0995684723a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kojic acid 40V, Negative-QTOF	splash10-0006-9000000000-63243637491eb161d9df	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01759

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Kojic_acid

METLIN ID

Not Available

PubChem Compound

3840

PDB ID

KOJ

ChEBI ID

43572

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1253161

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Kojic acid (HMDB0032923)

MOL for HMDB0032923 (Kojic acid)

3D MOL for HMDB0032923 (Kojic acid)

3D SDF for HMDB0032923 (Kojic acid)

3D-SDF for HMDB0032923 (Kojic acid)

PDB for HMDB0032923 (Kojic acid)

3D PDB for HMDB0032923 (Kojic acid)

SMILES for HMDB0032923 (Kojic acid)

INCHI for HMDB0032923 (Kojic acid)

Structure for HMDB0032923 (Kojic acid)

3D Structure for HMDB0032923 (Kojic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra