CHEBI:42017 - 2,4-dinitrophenol

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ChEBI Name 2,4-dinitrophenol
ChEBI ID CHEBI:42017
Definition A dinitrophenol having the nitro groups at the 2- and 4-positions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42013, CHEBI:918
Supplier Information ChemicalBook:CB4227430, eMolecules:36749948, eMolecules:1938357, eMolecules:529516
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Proflavine, also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. It has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic. Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. In the presence of light, proflavine can induce double-stranded breaks in DNA. Proflavine absorbs strongly in the blue region at 445 nm (in water at pH 7) with molar extinction coefficient of c. 40,000. Proflavin is a fluorescent dye that is sometimes used in microscopic in-vivo imaging due to its intercalation properties. However, there was concern that women exposed to proflavin could develop cervical cancer since they have mutagenesis potential. However, the retrospective analysis performed by Pantano et. al. demonstrated that there is no increased cervical cancer risk after exposure to proflavin.
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Formula C6H4N2O5
Net Charge 0
Average Mass 184.10640
Monoisotopic Mass 184.01202
InChI InChI=1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H
InChIKey UFBJCMHMOXMLKC-UHFFFAOYSA-N
SMILES Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O
Metabolite of Species Details
Nocardioides sp. (NCBI:txid35761) of strain JS1661 See: PubMed
Roles Classification
Biological Role(s): oxidative phosphorylation inhibitor
Any compound that inhibits oxidative phosphorylation.
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
bacterial xenobiotic metabolite
Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antiseptic drug
A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body).
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ChEBI Ontology
Outgoing 2,4-dinitrophenol (CHEBI:42017) has role allergen (CHEBI:50904)
2,4-dinitrophenol (CHEBI:42017) has role antiseptic drug (CHEBI:48218)
2,4-dinitrophenol (CHEBI:42017) has role bacterial xenobiotic metabolite (CHEBI:76976)
2,4-dinitrophenol (CHEBI:42017) has role geroprotector (CHEBI:176497)
2,4-dinitrophenol (CHEBI:42017) has role oxidative phosphorylation inhibitor (CHEBI:73267)
2,4-dinitrophenol (CHEBI:42017) is a dinitrophenol (CHEBI:39352)
2,4-dinitrophenol (CHEBI:42017) is conjugate acid of 2,4-dinitrophenol(1−) (CHEBI:84561)
Incoming 4,6-dinitro-o-cresol (CHEBI:39349) has functional parent 2,4-dinitrophenol (CHEBI:42017)
2,4-dinitrophenol(1−) (CHEBI:84561) is conjugate base of 2,4-dinitrophenol (CHEBI:42017)
IUPAC Name
2,4-dinitrophenol
Synonyms Sources
1-hydroxy-2,4-dinitrobenzene ChemIDplus
2,4-Dinitrophenol KEGG COMPOUND
2,4-DINITROPHENOL PDBeChem
2,4-DNP NIST Chemistry WebBook
α-dinitrophenol NIST Chemistry WebBook
Manual Xrefs Databases
2,4-Dinitrophenol Wikipedia
C02496 KEGG COMPOUND
CPD-8179 MetaCyc
DB04528 DrugBank
DNF PDBeChem
LSM-20951 LINCS
View more database links
Registry Numbers Types Sources
103005 Gmelin Registry Number Gmelin
1246142 Beilstein Registry Number Beilstein
1246142 Reaxys Registry Number Reaxys
51-28-5 CAS Registry Number ChemIDplus
51-28-5 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
10509480 PubMed citation Europe PMC
10888472 PubMed citation Europe PMC
13532746 PubMed citation Europe PMC
15307184 PubMed citation Europe PMC
16661637 PubMed citation Europe PMC
18505478 PubMed citation Europe PMC
25281383 PubMed citation Europe PMC
5959282 PubMed citation Europe PMC
9129253 PubMed citation Europe PMC
Last Modified
20 September 2021