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Details

Stereochemistry ACHIRAL
Molecular Formula C10H6O2
Molecular Weight 158.1538
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,4-NAPHTHOQUINONE

SMILES

c1ccc2c(c1)C(=O)C=CC2=O

InChI

InChIKey=FRASJONUBLZVQX-UHFFFAOYSA-N
InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

HIDE SMILES / InChI

Molecular Formula C10H6O2
Molecular Weight 158.1538
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

1,4-naphthoquinone is a chemical studied as a potential inhibitor of monoamine oxidase and DNA topoisomerase activities as well as acetyltransferase activity. 1,4-Naphthoquinone is a potent inhibitor of human cancer cell growth and angiogenesis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.8000000000000007 µM [IC50]
1.5 µM [Ki]
7.70000000000000018 µM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
A new naphthoquinone from Pyrola japonica.
2001 Dec
Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases.
2001 Mar
Mutational analyses of cysteine residues of bovine dihydrodiol dehydrogenase 3.
2001 May 5
Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen.
2002 Feb
Solubilization of a naphthoquinone derivative by hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and polyvinylpyrrolidone (PVP-K30). The influence of PVP-K30 and pH on solubilizing effect of HP-beta-CD.
2002 Jan-Feb
Cellular pharmacology studies of shikonin derivatives.
2002 May
Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.
2002 May
Cyclooxygenase-2 inhibitory 1,4-naphthoquinones from Impatiens balsamina L.
2002 May
Why do co-solvents enhance the solubility of solutes in supercritical fluids? New evidence and opinion.
2002 Nov 15
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.
2003 Feb
Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.
2003 Feb 25
[Succivil efficacy in endogenous intoxication].
2003 Jul-Aug
Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.
2003 Jul-Aug
A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS.
2003 Nov
Alternative quinone substrates and inhibitors of human electron-transfer flavoprotein-ubiquinone oxidoreductase.
2004 Mar 1
Patents

Sample Use Guides

In Vivo Use Guide
Rat LD50 (oral) 190mg/kg
Route of Administration: Oral
1,4-naphthoquinone exhibited cytotoxic
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:16:41 UTC 2021
Edited
by admin
on Sat Jun 26 13:16:41 UTC 2021
Record UNII
RBF5ZU7R7K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,4-NAPHTHOQUINONE
HSDB   MI  
Systematic Name English
1,4-NAPHTHOQUINONE [HSDB]
Common Name English
NAPHTHOQUINONE, 1,4-
Systematic Name English
1,4-NAPHTHOQUINONE [MI]
Common Name English
.ALPHA.-NAPHTHOQUINONE
Common Name English
1,4-DIHYDRO-1,4-DIKETONAPHTHALENE
Systematic Name English
NSC-9583
Code English
1,4-NAPHTHALENEDIONE
Systematic Name English
Code System Code Type Description
EPA CompTox
130-15-4
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
PUBCHEM
8530
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
HSDB
2037
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-977-6
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
FDA UNII
RBF5ZU7R7K
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
RXCUI
1602556
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M7750
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
1,4-NAPHTHOQUINONE
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
CAS
130-15-4
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
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