Diosquinone

Details

• Internal ID: 2e596157-a931-4b65-8c9f-f4b3d9af3636
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 3-hydroxy-4-(5-hydroxy-7-methyl-1,4-dioxonaphthalen-2-yl)-5-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C=C(C2=O)C3=C(C4=C(C=C3C)C(=O)C5C(C4=O)O5)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C=C(C2=O)C3=C(C4=C(C=C3C)C(=O)C5C(C4=O)O5)O
• InChI: InChI=1S/C22H14O7/c1-7-3-9-15(12(23)4-7)13(24)6-11(17(9)25)14-8(2)5-10-16(19(14)27)20(28)22-21(29-22)18(10)26/h3-6,21-23,27H,1-2H3
• InChI Key: AVBFKEHAFCGOKT-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₄O₇
• Molecular Weight: 390.30 g/mol
• Exact Mass: 390.07395278 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 50886-69-6
• NSC342731
• Batacanone
• 4-(1,4-Dihydro-5-hydroxy-7-methyl-1,4-dioxo-2-naphthalenyl)-1a,7a-dihydro-3-hydroxy-5-methylnaphth(2,3-b)oxirene-2,7-dione
• NSC 342731
• DIOSQUINONE & BATACANONE
• CHEMBL1984064
• DTXSID00965125
• NSC-342731
• 3-Hydroxy-4-(5-hydroxy-7-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-5-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
• NCI60_003044
• 3-hydroxy-4-(5-hydroxy-7-methyl-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-5-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
• 3-hydroxy-4-(5-hydroxy-7-methyl-1,4-dioxo-2-naphthyl)-5-methyl-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
• Naphth(2,3-b)oxirene-2,7-dione, 4-(1,4-dihydro-5-hydroxy-7-methyl-1,4-dioxo-2-naphthalenyl)-1a,7a-dihydro-3-hydroxy-5-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	-	0.5902	59.02%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7297	72.97%
OATP2B1 inhibitior	-	0.7127	71.27%
OATP1B1 inhibitior	+	0.8523	85.23%
OATP1B3 inhibitior	+	0.9310	93.10%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6938	69.38%
P-glycoprotein inhibitior	-	0.7091	70.91%
P-glycoprotein substrate	-	0.8478	84.78%
CYP3A4 substrate	+	0.5884	58.84%
CYP2C9 substrate	-	0.8057	80.57%
CYP2D6 substrate	-	0.8670	86.70%
CYP3A4 inhibition	-	0.7018	70.18%
CYP2C9 inhibition	+	0.7835	78.35%
CYP2C19 inhibition	+	0.7257	72.57%
CYP2D6 inhibition	-	0.8543	85.43%
CYP1A2 inhibition	-	0.5317	53.17%
CYP2C8 inhibition	-	0.6297	62.97%
CYP inhibitory promiscuity	+	0.7592	75.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.7403	74.03%
Skin irritation	-	0.6354	63.54%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6287	62.87%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.7177	71.77%
skin sensitisation	-	0.7136	71.36%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4005	40.05%
Estrogen receptor binding	+	0.6651	66.51%
Androgen receptor binding	+	0.6877	68.77%
Thyroid receptor binding	-	0.7366	73.66%
Glucocorticoid receptor binding	+	0.6584	65.84%
Aromatase binding	-	0.7473	74.73%
PPAR gamma	+	0.5491	54.91%
Honey bee toxicity	-	0.9285	92.85%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.96%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.19%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.84%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.56%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.79%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	90.93%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.61%	99.15%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.11%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.94%	94.00%
CHEMBL4530	P00488	Coagulation factor XIII	83.84%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.21%	96.21%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.55%	93.03%

Plants that contains it

• Diospyros batocana
• Diospyros chamaethamnus
• Diospyros mafiensis
• Diospyros mespiliformis
• Diospyros tricolor
• Diospyros verrucosa

Cross-Links

• PubChem: 122720
• LOTUS: LTS0160072
• wikiData: Q82947305