2-Methoxystypandrone

Details

• Internal ID: 9cfd82af-fc88-4a2e-9d30-6d33ea5f0ae7
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC2=C(C(=O)C=C(C2=O)OC)C(=C1C(=O)C)O
• SMILES (Isomeric): CC1=CC2=C(C(=O)C=C(C2=O)OC)C(=C1C(=O)C)O
• InChI: InChI=1S/C14H12O5/c1-6-4-8-12(14(18)11(6)7(2)15)9(16)5-10(19-3)13(8)17/h4-5,18H,1-3H3
• InChI Key: SSHJHOVVYKCJJI-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 85122-21-0
• 6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione
• 1,4-Naphthalenedione, 6-acetyl-5-hydroxy-2-methoxy-7-methyl-
• 2-Methoxy-6-acetyl-7-methyljuglone
• CHEMBL322776
• 6-acetyl-5-hydroxy-2-methoxy-7-methyl-naphthalene-1,4-dione
• DTXSID10234258
• CHEBI:169725
• 2-Methoxy-6-acethyl-7-methyljuglone
• BDBM50107000
• AKOS028108639
• 6-Acetyl-5-hydroxy-2-methoxy-7-methyl-[1,4]naphthoquinone
• 6-Acetyl-5-hydroxy-2-methoxy-7-methyl-1,4-naphthoquinone
• 6-acetyl-5-hydroxy-2-methoxy-7-methyl-1,4-dihydronaphthalene-1,4-dione
• 6-Acetyl-5-hydroxy-2-methoxy-7-methyl-2,3-dihydro-[1,4]naphthoquinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8320	83.20%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7664	76.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9533	95.33%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8976	89.76%
P-glycoprotein inhibitior	-	0.8862	88.62%
P-glycoprotein substrate	-	0.8916	89.16%
CYP3A4 substrate	-	0.5073	50.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.5470	54.70%
CYP2C9 inhibition	-	0.8896	88.96%
CYP2C19 inhibition	-	0.7045	70.45%
CYP2D6 inhibition	-	0.8647	86.47%
CYP1A2 inhibition	+	0.8847	88.47%
CYP2C8 inhibition	-	0.6393	63.93%
CYP inhibitory promiscuity	+	0.5439	54.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9156	91.56%
Carcinogenicity (trinary)	Non-required	0.5161	51.61%
Eye corrosion	-	0.9759	97.59%
Eye irritation	+	0.6616	66.16%
Skin irritation	-	0.6029	60.29%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7503	75.03%
Micronuclear	+	0.7359	73.59%
Hepatotoxicity	+	0.7093	70.93%
skin sensitisation	-	0.7584	75.84%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4949	49.49%
Acute Oral Toxicity (c)	II	0.6618	66.18%
Estrogen receptor binding	+	0.6387	63.87%
Androgen receptor binding	-	0.5650	56.50%
Thyroid receptor binding	-	0.8037	80.37%
Glucocorticoid receptor binding	-	0.7884	78.84%
Aromatase binding	-	0.5094	50.94%
PPAR gamma	-	0.5159	51.59%
Honey bee toxicity	-	0.9355	93.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.22%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.85%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.41%	85.14%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.17%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.21%	94.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.42%	92.68%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.95%	96.00%
CHEMBL2535	P11166	Glucose transporter	82.33%	98.75%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.14%	94.42%
CHEMBL4208	P20618	Proteasome component C5	81.27%	90.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.94%	96.67%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.66%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.48%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.12%	96.09%

Plants that contains it

• Aconitum seravschanicum
• Adansonia grandidieri
• Alkekengi officinarum
• Aphyllocladus denticulatus
• Bassia muricata
• Berchemia discolor
• Dendriopoterium menendezii
• Dianthera secunda
• Dodonaea viscosa
• Dysoxylum cumingianum
• Enceliopsis argophylla
• Flacourtia jangomas
• Galatella sedifolia subsp. sedifolia
• Lavandula angustifolia subsp. pyrenaica
• Miliusa velutina
• Neobalanocarpus heimii
• Onobrychis arenaria
• Psychotria stachyoides
• Reynoutria japonica
• Rumex japonicus
• Senecio subdentatus
• Senna didymobotrya
• Senna longiracemosa
• Teucrium yemense
• Trichotosia mollis
• Ventilago denticulata

Cross-Links

• PubChem: 158739
• NPASS: NPC254603
• ChEMBL: CHEMBL322776
• LOTUS: LTS0106925
• wikiData: Q72486064