Juglone

Details

• Internal ID: 346c46be-b7f1-4dad-adec-35cfe650ee09
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxynaphthalene-1,4-dione
• SMILES (Canonical): C1=CC2=C(C(=O)C=CC2=O)C(=C1)O
• SMILES (Isomeric): C1=CC2=C(C(=O)C=CC2=O)C(=C1)O
• InChI: InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
• InChI Key: KQPYUDDGWXQXHS-UHFFFAOYSA-N
• Popularity: 1,563 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆O₃
• Molecular Weight: 174.15 g/mol
• Exact Mass: 174.031694049 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 481-39-0
• 5-Hydroxy-1,4-naphthoquinone
• 5-Hydroxy-1,4-naphthalenedione
• 5-Hydroxynaphthalene-1,4-dione
• Regianin
• Nucin
• Juglon
• 5-Hydroxynaphthoquinone
• Akhnot
• Yuglon
• C.I. Natural Brown 7
• 8-Hydroxy-1,4-naphthoquinone
• 1,4-NAPHTHALENEDIONE, 5-HYDROXY-
• 5-Hydroxy-p-naphthoquinone
• C.I. 75500
• 1,4-Naphthoquinone, 5-hydroxy-
• Juglane
• Jugnlon
• Iuglon
• Caswell No. 515AA
• 1,4-Naphthoquinone, 8-hydroxy-
• 5-Hydroxy-1,4-naphthosemiquinone
• 5-Hydroxy-1,4-naftochinon
• NSC 153189
• NSC 622948
• CCRIS 5423
• 5-hydroxy-1,4-dihydronaphthalene-1,4-dione
• EINECS 207-567-5
• 5-Hydroxy-1,4-naftochinon [Czech]
• JUGLONE CRYSTALLIZED
• BRN 1909764
• UNII-W6Q80SK9L6
• CHEMBL43612
• W6Q80SK9L6
• 5-Hydroxy-[1,4]Naphthoquinone
• 8-Hydroxy-1,4-naphthalenedione
• CHEBI:15794
• NCI 2323
• NSC34266
• NSC153189
• NSC622948
• NSC-153189
• NSC-622948
• 481-13-0
• 1, 8-hydroxy-
• 4-08-00-02368 (Beilstein Handbook Reference)
• WLN: L66 BV EVJ GQ
• Antibiotic PD7
• 5-hydroxy-1,4- naphthalenedione
• Avastin+/-Tarceva
• MFCD00001684
• Spectrum_000415
• 3b7j
• JUGLONE [MI]
• Spectrum2_000778
• Spectrum3_001228
• Spectrum4_001769
• Spectrum5_000357
• D02FPF
• D08PZH
• D0C0NH
• 5-HNQ
• SCHEMBL34185
• BSPBio_001157
• BSPBio_002676
• KBioGR_000497
• KBioGR_002257
• KBioGR_002470
• KBioSS_000497
• KBioSS_000895
• KBioSS_002477
• SPECTRUM300038
• DivK1c_001026
• SPBio_000856
• -Hydroxy-1,4-naphthalenedione
• DTXSID0031504
• BDBM24777
• HMS503M13
• KBio1_001026
• KBio2_000497
• KBio2_000895
• KBio2_002470
• KBio2_003065
• KBio2_003463
• KBio2_005038
• KBio2_005633
• KBio2_006031
• KBio2_007606
• KBio3_000913
• KBio3_000914
• KBio3_002176
• KBio3_002948
• 5-hydroxy-naphthalene-1,4-dione
• cMAP_000058
• NINDS_001026
• Bio1_000441
• Bio1_000930
• Bio1_001419
• Bio2_000409
• Bio2_000889
• HMS1362I19
• HMS1792I19
• HMS1923G07
• HMS1990I19
• HMS3403I19
• Juglone - CAS 481-39-0
• 5-hydroxy-1,4-naphthoquinone, 4
• HY-N6949
• CCG-40256
• NSC-34266
• s5512
• ZB1862
• 5-Hydroxy-1,4-naphthoquinone, 97%
• AKOS001576598
• 5-Hydroxy-1,4-naphthalenedione, 9CI
• CS-W017516
• LS-2142
• SDCCGMLS-0066542.P001
• IDI1_001026
• IDI1_002164
• SMP1_000168
• NCGC00095247-01
• NCGC00095247-02
• NCGC00095247-03
• NCGC00095247-04
• NCGC00095247-05
• CI 75500
• CI-75500
• 1,4-dihydro-1,4-dioxo-5-hydroxynaphthalene
• AM20040546
• FT-0627559
• H0286
• C03840
• EN300-160375
• F17689
• A827478
• A936425
• Q900912
• SR-05000002406
• J-650071
• Q-100522
• SR-05000002406-1
• F0451-0746
• InChI=1/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8238	82.38%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7875	78.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9545	95.45%
OATP1B3 inhibitior	+	0.9806	98.06%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9422	94.22%
P-glycoprotein inhibitior	-	0.9674	96.74%
P-glycoprotein substrate	-	0.9568	95.68%
CYP3A4 substrate	-	0.6123	61.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.5825	58.25%
CYP2C19 inhibition	+	0.5098	50.98%
CYP2D6 inhibition	-	0.7642	76.42%
CYP1A2 inhibition	+	0.9247	92.47%
CYP2C8 inhibition	-	0.9555	95.55%
CYP inhibitory promiscuity	-	0.6480	64.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7709	77.09%
Carcinogenicity (trinary)	Warning	0.4730	47.30%
Eye corrosion	-	0.9098	90.98%
Eye irritation	+	0.9963	99.63%
Skin irritation	+	0.8347	83.47%
Skin corrosion	-	0.9717	97.17%
Ames mutagenesis	+	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9008	90.08%
Micronuclear	+	0.5949	59.49%
Hepatotoxicity	+	0.9375	93.75%
skin sensitisation	+	0.7238	72.38%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.7134	71.34%
Acute Oral Toxicity (c)	II	0.7268	72.68%
Estrogen receptor binding	+	0.6413	64.13%
Androgen receptor binding	-	0.5110	51.10%
Thyroid receptor binding	-	0.5567	55.67%
Glucocorticoid receptor binding	-	0.5502	55.02%
Aromatase binding	-	0.6441	64.41%
PPAR gamma	+	0.6272	62.72%
Honey bee toxicity	-	0.9750	97.50%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	12589.3 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	1995.3 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	4466.8 nM; 7943.3 nM; 1778.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	3162.3 nM; 5623.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	3162.3 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	19952.6 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	1000 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	10000 nM	Potency	via CMAUP
CHEMBL4804	P30305	Dual specificity phosphatase Cdc25B	1980 nM	IC50	PMID: 19028102
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	1000 nM	IC50	PMID: 18318466
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	7079.5 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	6309.6 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	7079.5 nM; 11220.2 nM; 14125.4 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	50118.7 nM; 8912.5 nM; 10000 nM; 39810.7 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	354.8 nM; 354.8 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.48%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.60%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.48%	91.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.60%	96.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.66%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.65%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.33%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.54%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.63%	82.69%
CHEMBL2535	P11166	Glucose transporter	82.28%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	82.02%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.22%	89.00%

Plants that contains it

• Carya illinoinensis
• Diospyros lycioides
• Drosera madagascariensis
• Euclea natalensis
• Foeniculum vulgare
• Juglans mandshurica
• Juglans nigra
• Juglans regia
• Lomatia hirsuta subsp. obliqua
• Platycarya strobilacea
• Pterocarya fraxinifolia
• Speranskia tuberculata

Cross-Links

• PubChem: 3806
• NPASS: NPC108288
• ChEMBL: CHEMBL43612
• LOTUS: LTS0110862
• wikiData: Q900912