Natural Product (NP) Details

General Information of the NP (ID: NP9143)
Name
1,4-naphthoquinone
Synonyms
1,4-NAPHTHOQUINONE; 130-15-4; naphthalene-1,4-dione; 1,4-Naphthalenedione; p-Naphthoquinone; NAPHTHOQUINONE; alpha-Naphthoquinone; 1,4-Naphthylquinone; 1,4-Naphthaquinone; USAF CY-10; 1,4-Dihydro-1,4-diketonaphthalene; 1,4-Naftochinon; RCRA waste number U166; 1,4-dihydronaphthalene-1,4-dione; UNII-RBF5ZU7R7K; NSC 9583; .alpha.-Naphthoquinone; MFCD00001676; RBF5ZU7R7K; CHEMBL55934; NQ-1; CHEBI:27418; NSC9583; 1,4-Naftochinon [Czech]; 1,4 naphthoquinone; CCRIS 5424; 1,4-naphtho-quinone; HSDB 2037; 1,4-Naphthoquinone, 99%, contains up to 6% water; EINECS 204-977-6; RCRA waste no. U166; napthoquinone; AI3-24292; naphthalene-1; Naphthoquinone #; Naphthoquinone 1; 1,4naphtaquinone; naphthoquinone group; 1,4-naphtoquinone; 1,4-diketonaphthalene; 1,4-naphthalene-dione; PubChem22093; ACMC-1BTZT; Spectrum2_000481; Spectrum3_000754; Spectrum4_001245; 1,4-naphtho-quinone, 3; DSSTox_CID_20704; WLN: L66 BV EVJ; DSSTox_GSID_40704; SCHEMBL42139; 1,4-Naphthoquinone, 97%; BSPBio_002368; KBioGR_001770; MLS000069814; SPBio_000341; DTXSID5040704; BDBM24776; KBio3_001588; ZINC901405; NSC-9583; Tox21_303967; ANW-19159; BBL025616; CCG-39519; s9342; SBB058659; STL146359; AKOS004907201; AKOS025243281; CS-W016206; FS-2704; HY-W015490; MCULE-4996549760; NE10115; NCGC00164067-01; NCGC00164067-02; NCGC00357275-01; AK-57313; CAS-130-15-4; SMR000059173; DB-005069; FT-0606918; N0040; ST51036980; C02617; 1,4-Naphthoquinone, purum, >=96.5% (HPLC); 1,4-Naphthalenedione-2,3,5,6,7,8-d6(9CI); Q161542; Q-200085; F0001-0400; Z1741972099; 1,4-Naphthoquinone, 97% (dry wt.), cont. up to 5% water; 26473-08-5
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Species Origin Setaria palmifolia ...     Click to Show/Hide
Setaria palmifolia
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Poales
Family: Poaceae
Genus: Setaria
Species: Setaria palmifolia
Disease Staphylococcus infection [ICD-11: 1C41] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.443
 
MDCK Permeability
 -4.52
 
PAMPA
 +++
 
HIA
 -
 
Distribution
VDss
 -0.104
 
PPB
 92.5%
 
BBB
 - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 - -
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 - -
CYP2D6 inhibitor
 +++
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 5.998
 
T1/2
 2.271
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 ++
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 +
 
Genotoxicity
 ++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C10H6O2
PubChem CID
8530
Canonical SMILES
C1=CC=C2C(=O)C=CC(=O)C2=C1
InChI
1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
InChIKey
FRASJONUBLZVQX-UHFFFAOYSA-N
CAS Number
CAS 130-15-4
ChEBI ID
CHEBI:27418
Herb ID
HBIN001534
TTD Drug ID
D0DQ6Z
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Imipenem + Cefuroxime + Cefotaxime     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Micrococcus luteus Microorganism model Micrococcus luteus
Bacillus cereus Microorganism model Bacillus cereus
Methicillin-sensitive Staphylococcus aureus Microorganism model Staphylococcus aureus
Methicillin-Resistant Staphylococcus aureus Microorganism model Staphylococcus aureus
Escherichia coli Microorganism model Escherichia coli
Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
Salmonella choleraesuis Microorganism model Salmonella choleraesuis
                    Experimental
                    Result(s)		 1,4-naphthoquinone combined with ascorbate have significant antitumor effects against MCF-7 cells in vitro and Ehrlich-ascites carcinoma in mice.
Target and Pathway
Target(s) Indoleamine 2,3-dioxygenase 1 (IDO1)  Molecule Info  [3]
Plasmodium dihydroorotate dehydrogenase (Malaria DHOdehase)  Molecule Info  [4]
BioCyc Superpathway of tryptophan utilization Click to Show/Hide
2 Tryptophan degradation
3 L-kynurenine degradation
4 Tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde
5 NAD de novo biosynthesis
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 Metabolic pathways
3 Tryptophan metabolism
4 African trypanosomiasis
NetPath Pathway TSLP Signaling Pathway Click to Show/Hide
2 IL5 Signaling Pathway
3 TGF_beta_Receptor Signaling Pathway
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
2 Tryptophan Metabolism
Reactome Pyrimidine biosynthesis Click to Show/Hide
2 Tryptophan catabolism
WikiPathways Metabolism of nucleotides Click to Show/Hide
2 Tryptophan metabolism
3 Metabolism of amino acids and derivatives
References
Reference 1 1,4-Naphthoquinone accumulates reactive oxygen species in Staphylococcus aureus: a promising approach towards effective management of biofilm threat. Arch Microbiol. 2021 Apr;203(3):1183-1193.
Reference 2 Synergistic Antibacterial Activity Between 1,4-Naphthoquinone and Beta-Lactam Antibiotics Against Methicillin-Resistant Staphylococcus aureus. Microb Drug Resist. 2021 Feb;27(2):234-240.
Reference 3 Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors. J Med Chem. 2008 Mar 27;51(6):1706-18.
Reference 4 Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76.
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