Thymoquinone

Details

• Internal ID: bcd8b121-d266-45a6-b3ad-57a455a511b6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Benzoquinones > P-benzoquinones
• IUPAC Name: 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CC1=CC(=O)C(=CC1=O)C(C)C
• SMILES (Isomeric): CC1=CC(=O)C(=CC1=O)C(C)C
• InChI: InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
• InChI Key: KEQHJBNSCLWCAE-UHFFFAOYSA-N
• Popularity: 2,004 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20 g/mol
• Exact Mass: 164.083729621 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 490-91-5
• Thymoquinon
• p-Cymene-2,5-dione
• 2-Isopropyl-5-methyl-1,4-benzoquinone
• p-Mentha-3,6-diene-2,5-dione
• 2-Isopropyl-5-methylbenzoquinone
• 2,5-CYCLOHEXADIENE-1,4-DIONE, 2-METHYL-5-(1-METHYLETHYL)-
• 2-Isopropyl-5-methyl-p-benzoquinone
• 2-Isopropyl-5-methylbenzo-1,4-quinone
• 5-Isopropyl-2-methyl-1,4-benzoquinone
• NSC 2228
• 2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
• 2-Methyl-5-isopropyl-p-benzoquinone
• 2-Isopropyl-5-methylcyclohexa-2,5-diene-1,4-dione
• CCRIS 7152
• NSC-2228
• EINECS 207-721-1
• O60IE26NUF
• BRN 1939047
• AI3-17758
• NSC2228
• 2,5-Cyclohexadiene-1,4-dione, 5-isopropyl-2-methyl-
• 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
• UNII-O60IE26NUF
• 2-Methyl-5-isopropyl-1,4-benzoquinone
• 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione
• CHEBI:113532
• 5-Isopropyl-2-methyl-p-benzoquinone
• 5-Isopropyl-2-methyl-2,5-Cyclohexadiene-1,4-dione
• thymolquinone
• Thymoil
• 4hco
• MFCD00001602
• p-Mentha-3,5-dione
• Spectrum_001237
• SpecPlus_000457
• Thymoquinone, >=98%
• Spectrum2_000700
• Spectrum3_001345
• Spectrum4_001895
• Spectrum5_000550
• BSPBio_003129
• KBioGR_002455
• KBioSS_001717
• DivK1c_006553
• SCHEMBL542535
• THYMOQUINONE [WHO-DD]
• SPBio_000859
• CHEMBL1672002
• DTXSID9060079
• KBio1_001497
• KBio2_001717
• KBio2_004285
• KBio2_006853
• KBio3_002349
• Thymoquinone, analytical standard
• 2-Methyl-5-iso-propylbenzoquinone
• BDBM166686
• BCP16946
• HY-D0803
• WLN: L6V DVJ B1 EY1&1
• 2,4-dione, 5-isopropyl-2-methyl-
• CCG-40027
• s4761
• AKOS003368628
• NCGC00178250-01
• NCGC00178250-05
• AS-11327
• LS-56283
• p-Mentha-3,6-diene-2,5-dione (8CI)
• 2-Isopropyl-5-methylbenzo-1,4-quinone #
• 2,4-dione, 2-methyl-5-(1-methylethyl)-
• CS-0012226
• FT-0612708
• T0795
• EN300-264364
• T72517
• A827656
• SR-05000002192
• Q7799650
• SR-05000002192-2
• W-202869
• BRD-K97566842-001-03-5
• 'Thymoquinone; 2-isopropyl-5-methylbenzo-1,4-quinone'
• Z1255372388
• '2-methyl-5-(1-methylethyl)cyclohexa-2,5-diene-1,4-dione'
• 2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione (F8)
• 2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione, 9CI
• ethyl 2-hydroxy-5-[[2-(trifluoromethyl)phenyl]carbamoyl]benzoate;Thymoquinon
• InChI=1/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H
• 73940-92-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.7743	77.43%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8182	81.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9700	97.00%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8873	88.73%
P-glycoprotein inhibitior	-	0.9629	96.29%
P-glycoprotein substrate	-	0.9781	97.81%
CYP3A4 substrate	-	0.6890	68.90%
CYP2C9 substrate	-	0.7739	77.39%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.8209	82.09%
CYP2C19 inhibition	-	0.7249	72.49%
CYP2D6 inhibition	-	0.8339	83.39%
CYP1A2 inhibition	-	0.7977	79.77%
CYP2C8 inhibition	-	0.9960	99.60%
CYP inhibitory promiscuity	-	0.6762	67.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6594	65.94%
Carcinogenicity (trinary)	Non-required	0.6030	60.30%
Eye corrosion	+	0.4638	46.38%
Eye irritation	+	0.9624	96.24%
Skin irritation	+	0.6827	68.27%
Skin corrosion	-	0.8590	85.90%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6934	69.34%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	+	0.9360	93.60%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	+	0.6210	62.10%
Acute Oral Toxicity (c)	II	0.6763	67.63%
Estrogen receptor binding	-	0.9568	95.68%
Androgen receptor binding	-	0.8494	84.94%
Thyroid receptor binding	-	0.8221	82.21%
Glucocorticoid receptor binding	-	0.8521	85.21%
Aromatase binding	-	0.9069	90.69%
PPAR gamma	-	0.9352	93.52%
Honey bee toxicity	-	0.9278	92.78%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9030	90.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	2180 nM	IC50	PMID: 25556101

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.97%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.28%	90.71%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	83.10%	85.94%
CHEMBL1937	Q92769	Histone deacetylase 2	82.62%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	81.28%	94.73%

Plants that contains it

• Ayapana triplinervis
• Brucea mollis
• Laggera decurrens
• Monarda fistulosa
• Mosla chinensis
• Nigella sativa
• Origanum dictamnus
• Plectranthus amboinicus
• Tetraclinis articulata
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 10281
• NPASS: NPC166788
• ChEMBL: CHEMBL1672002
• LOTUS: LTS0205347
• wikiData: Q7799650