Kojic acid

Details

• Internal ID: d7db4301-93a5-4077-a1cd-d1f089de4d52
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: 5-hydroxy-2-(hydroxymethyl)pyran-4-one
• SMILES (Canonical): C1=C(OC=C(C1=O)O)CO
• SMILES (Isomeric): C1=C(OC=C(C1=O)O)CO
• InChI: InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
• InChI Key: BEJNERDRQOWKJM-UHFFFAOYSA-N
• Popularity: 2,172 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆O₄
• Molecular Weight: 142.11 g/mol
• Exact Mass: 142.02660867 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 501-30-4
• 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
• 5-Hydroxy-2-(hydroxymethyl)-4-pyrone
• 5-hydroxy-2-(hydroxymethyl)pyran-4-one
• 4H-PYRAN-4-ONE, 5-HYDROXY-2-(HYDROXYMETHYL)-
• 5-Hydroxy-2-hydroxymethyl-4-pyrone
• acido kojico
• 2-Hydroxymethyl-5-hydroxy-gamma-pyrone
• Kojisaeure
• CCRIS 4131
• 2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one
• NSC 1942
• EINECS 207-922-4
• MFCD00006580
• UNII-6K23F1TT52
• BRN 0120895
• 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone
• DTXSID2040236
• CHEBI:43572
• AI3-02549
• HSDB 7664
• 6K23F1TT52
• NSC-1942
• 123712-78-7
• 5-Hydroxy-2-hydroxymethyl-pyran-4-one
• 5-Hydroxy-2-hydroxymethyl-4H-pyran-4-one
• Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)
• CHEMBL287556
• DTXCID0020236
• NSC1942
• 5-18-02-00516 (Beilstein Handbook Reference)
• NCGC00017325-03
• NCGC00017325-06
• KOJIC ACID (IARC)
• KOJIC ACID [IARC]
• KOJIC ACID (MART.)
• KOJIC ACID [MART.]
• CAS-501-30-4
• Spectrum_000191
• KOJIC ACID [MI]
• Spectrum2_001828
• Spectrum3_001704
• Spectrum4_000571
• Spectrum5_001085
• Natural Kojic Acid Powder
• D0F3CO
• KOJIC ACID [HSDB]
• KOJIC ACID [INCI]
• Kojic Acid Dipalmitate 5kg
• Oprea1_038773
• SCHEMBL36895
• BSPBio_003288
• KBioGR_001002
• KBioSS_000671
• KOJIC ACID [WHO-DD]
• BIDD:ER0501
• DivK1c_000923
• SPBio_001875
• Kojic acid, analytical standard
• MEGxm0_000388
• WLN: T6O DVJ B1Q EQ
• ACon1_000622
• BEJNERDRQOWKJM-UHFFFAOYSA-
• HMS502O05
• KBio1_000923
• KBio2_000671
• KBio2_003239
• KBio2_005807
• KBio3_002508
• NINDS_000923
• HMS3604L04
• KUC106760N
• TNP00261
• 2-Hydroxymethyl-5-hydroxy-?-pyrone
• Tox21_110814
• Tox21_113449
• BBL010645
• BDBM50031467
• CCG-38458
• s5174
• STK801688
• AKOS000120649
• Tox21_110814_1
• 5-Hydroxy-2-hydroxymethyl-I(3)-pyron
• DB01759
• HY-W050154
• IDI1_000923
• SMP1_000171
• NCGC00017325-01
• NCGC00017325-02
• NCGC00017325-04
• NCGC00017325-05
• NCGC00017325-10
• NCGC00142361-01
• NCGC00168903-01
• NCGC00168903-02
• NCGC00181145-01
• AC-11658
• AS-11648
• Kojic acid, purum, >=98.0% (HPLC)
• KSC-11-228-2
• SY018009
• 5- hydroxy- 2- hydroxymethyl- 4- pyrone
• 2-HYDROXYMETHYL-5-HYDROXY-4-PYRONE
• 2-Hydroxymethyl-5-hydroxy-4H-pyran-4-one
• LS-127450
• CS-0032701
• FT-0627581
• K0010
• K0012
• EN300-20919
• 4h-piran-4-ona, 5-hidroxi-2-(hidroximetil)-
• C91105
• K-7000
• 2-HYDROXYMETHYL-5-HYDROXY-.GAMMA.-PYRONE
• Q416285
• SR-01000945134
• SR-01000945134-1
• C65A72E0-0E46-4AF4-AA68-178ECA2E5FCC
• F0001-1307
• Z104484860
• InChI=1/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9139	91.39%
Caco-2	+	0.5133	51.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8131	81.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8971	89.71%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9784	97.84%
P-glycoprotein inhibitior	-	0.9790	97.90%
P-glycoprotein substrate	-	0.9904	99.04%
CYP3A4 substrate	-	0.7325	73.25%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8470	84.70%
CYP3A4 inhibition	-	0.9090	90.90%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9557	95.57%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9807	98.07%
CYP inhibitory promiscuity	-	0.7747	77.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7174	71.74%
Eye corrosion	-	0.9352	93.52%
Eye irritation	+	0.9604	96.04%
Skin irritation	-	0.5544	55.44%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8767	87.67%
Micronuclear	-	0.5401	54.01%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	+	0.5367	53.67%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.6371	63.71%
Acute Oral Toxicity (c)	III	0.6190	61.90%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.5381	53.81%
Thyroid receptor binding	-	0.8145	81.45%
Glucocorticoid receptor binding	-	0.7419	74.19%
Aromatase binding	-	0.7046	70.46%
PPAR gamma	-	0.6419	64.19%
Honey bee toxicity	-	0.9596	95.96%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.7578	75.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5485	P14920	D-amino-acid oxidase	2000 nM	IC50	PMID: 23683589
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL1973	P14679	Tyrosinase	22940 nM; 125000 nM; 9150 nM; 7400 nM; 66550 nM; 133400 nM; 16670 nM; 22940 nM; 125000 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	DOI: 10.1016/0960-894X(96)00221-1; PMID: 12880321; PMID: 26386819; PMID: 21334791; PMID: 19359068; PMID: 16919455; PMID: 16275084; PMID: 15125944; PMID: 14510598

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.70%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.63%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.08%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.34%	94.45%
CHEMBL2581	P07339	Cathepsin D	83.45%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	81.42%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.80%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.49%	89.67%

Plants that contains it

• Chaenomeles sinensis
• Glycine max
• Marrubium cylleneum

Cross-Links

• PubChem: 3840
• NPASS: NPC116366
• ChEMBL: CHEMBL287556
• LOTUS: LTS0125477
• wikiData: Q416285