7-Methyljuglone

Details

• Internal ID: b873b4c3-4995-46d8-81d1-54b7afcacc19
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-7-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC2=C(C(=O)C=CC2=O)C(=C1)O
• SMILES (Isomeric): CC1=CC2=C(C(=O)C=CC2=O)C(=C1)O
• InChI: InChI=1S/C11H8O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h2-5,14H,1H3
• InChI Key: OZUSCVSONBBWOR-UHFFFAOYSA-N
• Popularity: 33 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₈O₃
• Molecular Weight: 188.18 g/mol
• Exact Mass: 188.047344113 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Ramentaceone
• 14787-38-3
• 5-hydroxy-7-methylnaphthalene-1,4-dione
• 7-Methyljuglon
• JUGLONE, 7-METHYL-
• 5-Hydroxy-7-methyl-1,4-naphthoquinone
• 5-Hydroxy-7-methyl-1,4-naphthalenedione
• 1,4-Naphthalenedione, 5-hydroxy-7-methyl-
• NSC208733
• ZS3RW9P6DY
• 1,4-NAPHTHOQUINONE, 5-HYDROXY-7-METHYL-
• NSC 208733
• NSC 624625
• BRN 2047829
• 5-Hydroxy-7-methyl-2,3-dihydronaphthal-ene-1,4-dione
• CHEBI:8773
• CHEMBL430853
• 4-08-00-02374 (Beilstein Handbook Reference)
• NSC624625
• NSC-208733
• NSC-624625
• 5-hydroxy-7-methyl-naphthalene-1,4-dione
• 7-Methyl juglon
• Ramentaceone (6CI)
• UNII-ZS3RW9P6DY
• 1, 5-hydroxy-7-methyl-
• SCHEMBL5904880
• DTXSID80163824
• BDBM50107009
• AKOS006278204
• 5-Hydroxy-7-methyl-[1,4]naphthoquinone
• 5-Hydroxy-7-methyll-,1,4-naphtoquinone
• LS-95647
• NCI60_001745
• NCI60_007460
• FT-0728797
• 1,4-Naphthalenedione, 5-hydroxy-7-methyl- (9CI)
• 5-hydroxy-7-methyl-1,4-dihydronaphthalene-1,4-dione
• Q27108145
• N-(3,4-Diethyloxy)phenylethyl-3,4-diethyloxyphenylacetamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8452	84.52%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8329	83.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9319	93.19%
OATP1B3 inhibitior	+	0.9862	98.62%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9231	92.31%
P-glycoprotein inhibitior	-	0.9644	96.44%
P-glycoprotein substrate	-	0.9793	97.93%
CYP3A4 substrate	-	0.5910	59.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.7985	79.85%
CYP2C9 inhibition	+	0.6892	68.92%
CYP2C19 inhibition	-	0.5444	54.44%
CYP2D6 inhibition	-	0.7902	79.02%
CYP1A2 inhibition	+	0.9548	95.48%
CYP2C8 inhibition	-	0.9669	96.69%
CYP inhibitory promiscuity	-	0.6194	61.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7709	77.09%
Carcinogenicity (trinary)	Non-required	0.4622	46.22%
Eye corrosion	-	0.9158	91.58%
Eye irritation	+	0.9769	97.69%
Skin irritation	+	0.7651	76.51%
Skin corrosion	-	0.8925	89.25%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8401	84.01%
Micronuclear	+	0.5949	59.49%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	+	0.5736	57.36%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5960	59.60%
Acute Oral Toxicity (c)	II	0.7955	79.55%
Estrogen receptor binding	-	0.5583	55.83%
Androgen receptor binding	+	0.6185	61.85%
Thyroid receptor binding	-	0.7744	77.44%
Glucocorticoid receptor binding	-	0.6456	64.56%
Aromatase binding	-	0.7359	73.59%
PPAR gamma	-	0.5998	59.98%
Honey bee toxicity	-	0.9757	97.57%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9760	97.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	28000 nM	IC50	PMID: 27173800

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.49%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.70%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	88.25%	91.49%
CHEMBL4208	P20618	Proteasome component C5	88.17%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.01%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.91%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.53%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.27%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.97%	93.03%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.42%	96.95%

Plants that contains it

• Dionaea muscipula
• Diospyros batocana
• Diospyros chamaethamnus
• Diospyros chloroxylon
• Diospyros ferrea
• Diospyros greenwayi
• Diospyros hallieri
• Diospyros hebecarpa
• Diospyros heterotricha
• Diospyros ismailii
• Diospyros kaki
• Diospyros lotus
• Diospyros loureiroana subsp. loureiroana
• Diospyros lycioides
• Diospyros mafiensis
• Diospyros mannii
• Diospyros maritima
• Diospyros paniculata
• Diospyros verrucosa
• Diospyros virginiana
• Diospyros zombensis
• Drosera capensis
• Drosera intermedia
• Drosera madagascariensis
• Drosera ramentacea
• Drosera rotundifolia
• Euclea divinorum
• Euclea natalensis
• Jasminum sambac
• Uvaria kirkii

Cross-Links

• PubChem: 26905
• NPASS: NPC307174
• ChEMBL: CHEMBL430853
• LOTUS: LTS0242366
• wikiData: Q27108145