kojic acid (CHEBI:43572)

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CHEBI:43572 - kojic acid

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ChEBI Name	kojic acid

ChEBI ID	CHEBI:43572

Definition	A pyranone that is 4H-pyran substituted by a hydroxy group at position 5, a hydroxymethyl group at position 2 and an oxo group at position 4. It has been isolated from the fungus Aspergillus oryzae.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:43568, CHEBI:34805

Supplier Information	ChemicalBook:CB8120056, eMolecules:876432, Selleckchem:Gefitinib, ZINC000019632614

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

Mrv0541 02271410443D

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Time for openFile(

Mrv0541 02271410443D

16 16 0 0 0 0 999 V2000

0.6435 -0.2794 -0.2672 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4264 -0.8412 0.3457 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.1017 1.8173 0.1765 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3706 -0.0064 0.8897 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7253 0.9888 -0.3037 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2074 1.3600 0.8054 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3473 -0.4966 1.4407 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0213 2.1502 1.2754 O 0 0 0 0 0 0 0 0 0 0 0 0

1.6862 -1.0705 -0.8819 C 0 0 2 0 0 0 0 0 0 0 0 0

1.1238 -1.8710 -1.9177 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5287 -1.8305 0.3969 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0844 2.7881 0.0774 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7414 1.8528 1.6844 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1533 -1.7113 -0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4667 -0.4428 -1.3184 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8618 -2.4075 -2.2725 H 0 0 0 0 0 0 0 0 0 0 0 0

1 9 1 0 0 0 0

1 2 2 0 0 0 0

4 2 1 0 0 0 0

4 7 2 0 0 0 0

3 5 1 0 0 0 0

5 1 1 0 0 0 0

4 6 1 0 0 0 0

6 3 2 0 0 0 0

6 8 1 0 0 0 0

9 10 1 0 0 0 0

2 11 1 0 0 0 0

3 12 1 0 0 0 0

8 13 1 0 0 0 0

9 14 1 0 0 0 0

9 15 1 0 0 0 0

10 16 1 0 0 0 0

M END): 20 ms

reading 16 atoms

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16 atoms created

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Wikipedia	License
Gefitinib, sold under the brand name Iressa, is a medication used for certain breast, lung and other cancers. Gefitinib is an EGFR inhibitor, like erlotinib, which interrupts signaling through the epidermal growth factor receptor (EGFR) in target cells. Therefore, it is only effective in cancers with mutated and overactive EGFR, but resistances to gefitinib can arise through other mutations. It is marketed by AstraZeneca and Teva. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.
Read full article at Wikipedia

Formula

C6H6O4

Net Charge

Average Mass

142.10940

Monoisotopic Mass

142.02661

InChI

InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2

InChIKey

BEJNERDRQOWKJM-UHFFFAOYSA-N

SMILES

OCc1cc(=O)c(O)co1

Metabolite of Species	Details
Aspergillus oryzae (NCBI:txid5062)	See: PubMed

Roles Classification
Biological Role(s):	NF-kappaB inhibitor An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA. Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . EC 1.10.3.1 (catechol oxidase) inhibitor Any EC 1.10.3.* (oxidoreductase acting on diphenols and related substances as donors with oxygen as acceptor) inhibitor that interferes with the action of catechol oxidase (EC 1.10.3.1). EC 1.10.3.2 (laccase) inhibitor Any EC 1.10.3.* (oxidoreductase acting on diphenols and related substances as donors with oxygen as acceptor) inhibitor that interferes with the action of laccase (EC 1.10.3.2). EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor Any EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 O atoms) inhibitor that interferes with the action of quercetin 2,3-dioxygenase (EC 1.13.1.24). EC 1.14.18.1 (tyrosinase) inhibitor Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. EC 1.4.3.3 (D-amino-acid oxidase) inhibitor Any EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of D-amino-acid oxidase (EC 1.4.3.3).

Application(s):	skin lightening agent Any cosmetic used to lighten the colour of skin by reducing the concentration of melanin.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	kojic acid (CHEBI:43572) has parent hydride 4H-pyran (CHEBI:35593) kojic acid (CHEBI:43572) has role Aspergillus metabolite (CHEBI:76956) kojic acid (CHEBI:43572) has role EC 1.10.3.1 (catechol oxidase) inhibitor (CHEBI:85049) kojic acid (CHEBI:43572) has role EC 1.10.3.2 (laccase) inhibitor (CHEBI:85050) kojic acid (CHEBI:43572) has role EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor (CHEBI:85051) kojic acid (CHEBI:43572) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997) kojic acid (CHEBI:43572) has role EC 1.4.3.3 (D-amino-acid oxidase) inhibitor (CHEBI:85052) kojic acid (CHEBI:43572) has role NF-κB inhibitor (CHEBI:73240) kojic acid (CHEBI:43572) has role skin lightening agent (CHEBI:85046) kojic acid (CHEBI:43572) is a 4-pyranones (CHEBI:131906) kojic acid (CHEBI:43572) is a enol (CHEBI:33823) kojic acid (CHEBI:43572) is a primary alcohol (CHEBI:15734)

IUPAC Name

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

Synonyms	Sources
5-Hydroxy-2-(hydroxymethyl)-4-pyrone	KEGG COMPOUND
5-hydroxy-2-hydroxymethyl-4-pyrone	ChemIDplus
ácido kójico	ChEBI
Kojic acid	KEGG COMPOUND
Kojisäure	ChEBI

Manual Xrefs	Databases
3977	DrugCentral
AU2012268879	Patent
C14516	KEGG COMPOUND
DB01759	DrugBank
HMDB0032923	HMDB
JP2013017408	Patent
KOJ	PDBeChem
KOJIC-ACID	MetaCyc
Kojic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
120895	Beilstein Registry Number	Beilstein
120895	Reaxys Registry Number	Reaxys
3620	Gmelin Registry Number	Gmelin
501-30-4	CAS Registry Number	KEGG COMPOUND
501-30-4	CAS Registry Number	ChemIDplus
501-30-4	CAS Registry Number	NIST Chemistry WebBook

Citations

Last Modified

19 June 2017

CHEBI:43572 - kojic acid

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