1,4-Naphthoquinone

Details

• Internal ID: d5097b77-e204-4666-b52b-fd8d55d7e57a
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: naphthalene-1,4-dione
• SMILES (Canonical): C1=CC=C2C(=O)C=CC(=O)C2=C1
• SMILES (Isomeric): C1=CC=C2C(=O)C=CC(=O)C2=C1
• InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
• InChI Key: FRASJONUBLZVQX-UHFFFAOYSA-N
• Popularity: 4,786 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆O₂
• Molecular Weight: 158.15 g/mol
• Exact Mass: 158.036779430 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.62
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 130-15-4
• naphthalene-1,4-dione
• 1,4-Naphthalenedione
• p-Naphthoquinone
• NAPHTHOQUINONE
• alpha-Naphthoquinone
• a-naphthoquinone
• 1,4-Naphthylquinone
• 1,4-Dihydro-1,4-diketonaphthalene
• 1,4-Naphthaquinone
• USAF CY-10
• 1,4-Naftochinon
• RCRA waste number U166
• 1,4-dihydronaphthalene-1,4-dione
• .alpha.-Naphthoquinone
• 1,4-Naftochinon [Czech]
• NSC 9583
• CCRIS 5424
• 1,4-naphtho-quinone
• HSDB 2037
• Naphthoquinone, 1,4-
• EINECS 204-977-6
• UNII-RBF5ZU7R7K
• RBF5ZU7R7K
• RCRA waste no. U166
• CHEMBL55934
• AI3-24292
• NQ-1
• DTXSID5040704
• CHEBI:27418
• NSC9583
• NSC-9583
• 1,4 naphthoquinone
• napthoquinone
• p-Naftoquinona
• naphthalene-1
• Naphthoquinone #
• Naphthoquinone 1
• 1,4naphtaquinone
• para-naphthoquinone
• 1,4-Naftoquinona
• 1,4-naphtoquinone
• .Alfa.-Naftoquinona
• 1,4-Naftalenodiona
• 1,4-Naphtilquinone
• MFCD00001676
• 1 4-Naphthylquinone
• 1,4-diketonaphthalene
• 1,4-naphthalene-dione
• Dithianon metabolite NQ
• Spectrum2_000481
• Spectrum3_000754
• Spectrum4_001245
• 1,4-naphtho-quinone, 3
• D09LVO
• D0DQ6Z
• 14-Naphthoquinone (8CI)
• WLN: L66 BV EVJ
• SCHEMBL42139
• 1 4-Naphthoquinone (8CI)
• 1,4-Naphthoquinone, 97%
• BSPBio_002368
• KBioGR_001770
• MLS000069814
• SPBio_000341
• DTXCID3020704
• BDBM24776
• KBio3_001588
• 14-Dihydro-14-diketonaphthalene
• 1,4-dihidro-1,4-dicetonaftaleno
• 1,4-NAPHTHOQUINONE [MI]
• 1,4-NAPHTHOQUINONE [HSDB]
• 1 4-Dihydro-1 4-diketonaphthalene
• Tox21_303967
• CCG-39519
• s9342
• STL146359
• AKOS004907201
• AKOS025243281
• CS-W016206
• FS-2704
• HY-W015490
• NSC 113960
• NCGC00164067-01
• NCGC00164067-02
• NCGC00357275-01
• AC-34538
• CAS-130-15-4
• LS-95611
• SMR000059173
• FT-0606918
• N0040
• EN300-21246
• C02617
• D70977
• 1,4-Naphthoquinone, purum, >=96.5% (HPLC)
• Q161542
• Q-200085
• Z104494806
• 1,4-Naphthoquinone, 97% (dry wt.), cont. up to 5% water
• InChI=1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8501	85.01%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6497	64.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9714	97.14%
OATP1B3 inhibitior	+	0.9757	97.57%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8927	89.27%
P-glycoprotein inhibitior	-	0.9748	97.48%
P-glycoprotein substrate	-	0.9896	98.96%
CYP3A4 substrate	-	0.7358	73.58%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8099	80.99%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	+	0.8085	80.85%
CYP2C19 inhibition	+	0.7633	76.33%
CYP2D6 inhibition	+	0.5518	55.18%
CYP1A2 inhibition	+	0.9232	92.32%
CYP2C8 inhibition	-	0.9881	98.81%
CYP inhibitory promiscuity	+	0.5354	53.54%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7898	78.98%
Carcinogenicity (trinary)	Non-required	0.5631	56.31%
Eye corrosion	-	0.8606	86.06%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.6803	68.03%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8417	84.17%
Micronuclear	-	0.6318	63.18%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	+	0.9311	93.11%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.7810	78.10%
Acute Oral Toxicity (c)	II	0.7364	73.64%
Estrogen receptor binding	-	0.7357	73.57%
Androgen receptor binding	-	0.6121	61.21%
Thyroid receptor binding	-	0.6357	63.57%
Glucocorticoid receptor binding	-	0.8557	85.57%
Aromatase binding	-	0.7014	70.14%
PPAR gamma	-	0.7533	75.33%
Honey bee toxicity	-	0.9377	93.77%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9439	94.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3587	Q02750	Dual specificity mitogen-activated protein kinase kinase 1	380 nM	IC50	PMID: 18077363
CHEMBL4804	P30305	Dual specificity phosphatase Cdc25B	2760 nM	IC50	PMID: 19028102
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	990 nM; 990 nM; 460 nM	IC50; IC50; IC50	PMID: 18318466; PMID: 20580138; via Super-PRED
CHEMBL1951	P21397	Monoamine oxidase A	7700 nM	Ki	PMID: 22071524
CHEMBL2039	P27338	Monoamine oxidase B	1500 nM	Ki	PMID: 22071524
CHEMBL4282	P31749	Serine/threonine-protein kinase AKT	10980 nM	IC50	PMID: 24321345

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.66%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.63%	98.95%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	88.04%	96.67%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.72%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.79%	91.11%

Plants that contains it

• Arnebia euchroma
• Arnebia guttata
• Juglans regia
• Lawsonia inermis

Cross-Links

• PubChem: 8530
• NPASS: NPC215008
• ChEMBL: CHEMBL55934
• LOTUS: LTS0176662
• wikiData: Q161542