Dithymoquinone

Details

• Internal ID: cb2fcee2-f707-49bf-8407-bc0818fa056c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Ileabethane, pseudopterane or nor-sandresane diterpenoids
• IUPAC Name: 4b,8b-dimethyl-3,7-di(propan-2-yl)-4a,8a-dihydrobiphenylene-1,4,5,8-tetrone
• SMILES (Canonical): CC(C)C1=CC(=O)C2(C(C1=O)C3(C2C(=O)C(=CC3=O)C(C)C)C)C
• SMILES (Isomeric): CC(C)C1=CC(=O)C2(C(C1=O)C3(C2C(=O)C(=CC3=O)C(C)C)C)C
• InChI: InChI=1S/C20H24O4/c1-9(2)11-7-13(21)19(5)17(15(11)23)20(6)14(22)8-12(10(3)4)16(24)18(19)20/h7-10,17-18H,1-6H3
• InChI Key: FPRGRROJPRIHJP-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 68.30 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.71
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 39461-20-6
• RefChem:927753
• Dithymoquinone
• SCHEMBL29453831
• DTXSID701045771
• NSC709309
• NSC-709309
• 4b,8b-dimethyl-3,7-di(propan-2-yl)-4a,8a-dihydrobiphenylene-1,4,5,8-tetrone
• Q15633913

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.4939	49.39%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7495	74.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9419	94.19%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8327	83.27%
P-glycoprotein inhibitior	-	0.6115	61.15%
P-glycoprotein substrate	-	0.9484	94.84%
CYP3A4 substrate	-	0.5698	56.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8844	88.44%
CYP3A4 inhibition	+	0.5272	52.72%
CYP2C9 inhibition	-	0.6916	69.16%
CYP2C19 inhibition	-	0.6719	67.19%
CYP2D6 inhibition	-	0.8383	83.83%
CYP1A2 inhibition	-	0.7800	78.00%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8466	84.66%
Carcinogenicity (trinary)	Non-required	0.4524	45.24%
Eye corrosion	-	0.9705	97.05%
Eye irritation	-	0.8626	86.26%
Skin irritation	-	0.6063	60.63%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.6937	69.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5635	56.35%
Micronuclear	+	0.5074	50.74%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	+	0.6959	69.59%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.6750	67.50%
Acute Oral Toxicity (c)	III	0.4450	44.50%
Estrogen receptor binding	+	0.6544	65.44%
Androgen receptor binding	+	0.6564	65.64%
Thyroid receptor binding	+	0.5558	55.58%
Glucocorticoid receptor binding	-	0.7342	73.42%
Aromatase binding	-	0.5950	59.50%
PPAR gamma	-	0.5365	53.65%
Honey bee toxicity	-	0.8618	86.18%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9787	97.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.95%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.38%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.13%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.53%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.34%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.81%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	80.68%	94.75%

Plants that contains it

• Nigella sativa

Cross-Links

• PubChem: 398941
• LOTUS: LTS0024603
• wikiData: Q15633913