Compounds > 4-nitrophenylalanine
Page last updated: 2024-11-06

4-nitrophenylalanine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-Nitrophenylalanine (4-NPA) is a synthetic analog of the amino acid phenylalanine, modified by the addition of a nitro group at the para position. It is an important tool for studying protein structure and function, as it can be incorporated into proteins during biosynthesis, acting as a structural probe. 4-NPA can be synthesized via various methods, such as the nitration of phenylalanine or the condensation of nitro-substituted benzaldehydes with glycine. 4-NPA's presence in a protein can be detected by its distinct UV absorbance at 310 nm, and its incorporation can lead to changes in protein structure and stability due to the nitro group's electronic and steric effects. Studies have shown that 4-NPA can affect protein folding, enzyme activity, and even protein-protein interactions. These effects can be exploited to study protein dynamics and the role of specific amino acids in protein function. Importantly, 4-NPA's properties make it useful in the development of fluorescent probes for bioimaging and in the design of novel pharmaceuticals.'

4-nitrophenylalanine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65089
CHEBI ID48496
SCHEMBL ID26443
SCHEMBL ID14904486
MeSH IDM0119919

Synonyms (57)

Synonym
2922-40-9
nsc-14786
nsc14786
dl-p-nitrophenylalanine
nsc-152925
1991-83-9
nsc148865
l-.beta.-nitrophenylalanine
wln: wnr d1yzvq -l
nsc152925
l-3-(p-nitrophenyl)alanine
nsc-148865
wln: wnr d1yzvq
4-nitro-dl-phenylalanine, 98%
SR-01000634331-1
4-nitrophenylalanine
CHEBI:48496
p-nitrophenylalanine
AKOS000187404
2-amino-3-(4-nitrophenyl)propanoic acid
p-nitro-dl-phenylalanine
ai3-52611
4-nitro-dl-phenylalanine
p-nitrophenylalanine, dl-
einecs 220-868-6
nsc 14786
dl-phenylalanine, 4-nitro-
phenylalanine, 4-nitro-
nsc 148865
FT-0627632
FT-0624396
FT-0634555
h-dl-phe(4-no2)-oh
SCHEMBL26443
2-amino-3-(4-nitrophenyl)propionic acid
AKOS016843486
NCGC00253665-01
SCHEMBL14904486
4-nitrophenylalanine #
N0952
mfcd00051221
mfcd00066016
mfcd00007384
4-nitro-dl-phenylalanine (h-dl-phe(4-no2)-oh)
J-017441
h-p-nitro-dl-phe-oh
d,l-p-nitrophenylalanine
4-nitro-d,l-phenylalanine
AS-38157
Q27121246
EN300-123066
CS-W015121
DTXSID40862482
HY-W014405
SY037130
SY015497
PD196703
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (8.70)18.7374
1990's6 (26.09)18.2507
2000's5 (21.74)29.6817
2010's10 (43.48)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.82 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.89 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
anthranilic acid
anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.		1.9910aminobenzoic acidhuman metabolite;
mouse metabolite
dapsone
[no description available]		2.0810substituted aniline;
sulfone		anti-inflammatory drug;
antiinfective agent;
antimalarial;
leprostatic drug
glutaral
Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.		2.0110dialdehydecross-linking reagent;
disinfectant;
fixative
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		2.4420alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
aspartic acid
Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.		2.1710aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		3.2660amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		4.5230amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
asparagine
Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.		2.1710amino acid zwitterion;
asparagine;
aspartate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		2.4120erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
phosphotyrosine
Phosphotyrosine: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis.. O(4)-phospho-L-tyrosine : A non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group.		2.0110L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid;
O(4)-phosphotyrosine		Escherichia coli metabolite;
immunogen
azides
Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.		2.0510pseudohalide anionmitochondrial respiratory-chain inhibitor
peroxynitrous acid
Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).		2.4420nitrogen oxoacid
dehydroalanine
2-ammonioprop-2-enoate : An amino acid zwitterion resulting from a transfer of a proton from the carboxy group to the amino group of 2-aminoacrylic acid.. 2-aminoacrylic acid : A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.		1.98102,3-dehydroamino acid;
alpha,beta-unsaturated monocarboxylic acid;
amino acid zwitterion;
enamine;
non-proteinogenic alpha-amino acid		alkylating agent;
human metabolite;
mouse metabolite
4-boronophenylalanine
4-boronophenylalanine: neutron absorbing (10)B-cpd used in thermal neutron capturetherapy of malignant melanoma; RN given refers to (L)-isomer; structure given in first source		2.0510
biotin
vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.		2.0110biotins;
vitamin B7		coenzyme;
cofactor;
Escherichia coli metabolite;
fundamental metabolite;
human metabolite;
mouse metabolite;
nutraceutical;
prosthetic group;
Saccharomyces cerevisiae metabolite
3-nitrotyrosine
3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.		2.74302-nitrophenols;
C-nitro compound;
nitrotyrosine;
non-proteinogenic alpha-amino acid
tyrosine o-sulfate
O(4')-sulfo-L-tyrosine : An O-sulfoamino acid that is L-tyrosine in which the phenolic hydrogen has been replaced by a sulfo group.		2.0610aryl sulfate;
L-tyrosine derivative;
O-sulfoamino acid		human metabolite
p-cyanophenylalanine
p-cyanophenylalanine: structure in first source		2.1710
4-azidophenylalanine
4-azidophenylalanine: RN given refers to (L)-isomer. 4-azido-L-phenylalanine : A 4-azidophenylalanine that has L-configuration. It is used as a bioorthogonal click-chemistry reagent.. 4-azidophenylalanine : A phenylalanine derivative that is phenylalanine substituted by an azido group at position 4.		2.0510
3-aminotyrosine
[no description available]		2.0110
sodium borohydride
sodium borohydride: RN given refers to parent cpd		1.9810inorganic sodium salt;
metal tetrahydridoborate
3-tyrosine
3-tyrosine: RN given refers to cpd with unspecified isomeric designation. L-m-tyrosine : A hydroxyphenylalanine that is L-phenylalanine with a substituent hydroxy group at position 3.		2.0710hydroxyphenylalanine;
L-alpha-amino acid zwitterion;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
phenols		plant metabolite
4-benzoylphenylalanine
4-benzoylphenylalanine: structure in first source; do not confuse with N-benzoylphenylalanine		2.0510
angiotensinogen
Angiotensinogen: An alpha-globulin of about 453 amino acids, depending on the species. It is produced by the liver in response to lowered blood pressure and secreted into blood circulation. Angiotensinogen is the inactive precursor of the ANGIOTENSINS produced in the body by successive enzyme cleavages. Cleavage of angiotensinogen by RENIN yields the decapeptide ANGIOTENSIN I. Further cleavage of angiotensin I (by ANGIOTENSIN CONVERTING ENZYME) yields the potent vasoconstrictor octapeptide ANGIOTENSIN II; and then, via other enzymes, other angiotensins also involved in the hemodynamic-regulating RENIN-ANGIOTENSIN SYSTEM.		1.9810
anticodon
Anticodon: The sequential set of three nucleotides in TRANSFER RNA that interacts with its complement in MESSENGER RNA, the CODON, during translation in the ribosome.		2.4220
epidermal growth factor
Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
Bone Loss, Osteoclastic
[description not available]		02.1710
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		01.9610