Page last updated: 2024-12-05

alpha-chlorohydrin

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Description

alpha-Chlorohydrin: A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-chloropropane-1,2-diol : A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3. [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]

Cross-References

ID SourceID
PubMed CID7290
CHEMBL ID3185949
CHEBI ID18721
SCHEMBL ID19213
MeSH IDM0000786

Synonyms (134)

Synonym
a-chlorohydrin
3-mcpd
3-monochloropropane-1,2-diol
3-chloro-propane-1,2-diol
MLS000028887
CHEBI:18721 ,
3-monochloro-1,2-propanediol
1-chloro-2,3-propanediol
smr000059152
(rs)-3-chloro-1,2-propanediol
alpha-chlorohydrin
chlorodeoxyglycerol
1,2-propanediol, 3-chloro-
.alpha.-chlorohydrin
epibloc
3-chloro-1,2-dihydroxypropane
chlorohydrin
2,3-dihydroxypropyl chloride
chloropropylene glycol
chloro-1,2-propanediol
3-chloropropylene glycol
glycerine alpha-monochlorohydrin
1-chloropropane-2,3-diol
chloro-1,2-dihydroxypropane
u-5897
monochlorohydrin
glycerol chlorohydrin
1-chloro-2,3-dihydroxypropane
glycerol alpha-monochlorohydrin
3-chloro-1,2-propanediol
96-24-2
3-chloropropane-1,2-diol
glycerin alpha-monochlorhydrin
ccris 4607
hsdb 2052
einecs 202-492-4
u 5897
3-chloro-1,2-propylene glycol
(+-)-2,3-dihydroxychloropropane
epa pesticide chemical code 117101
1-chloro-1-deoxyglycerol
1,2-dihydroxy-3-chloropropane
chloropropanediol
glyceryl-alpha-chlorohydrin
glycerol 3-chlorohydrin
brn 0635684
beta,beta'-dihydroxyisopropyl chloride
glyceryl chloride
glycerin epichlorohydrin
1,2-propanediol, 3-dichloro-
ai3-11200
glyceryl alpha-chlorohydrin
chlorhydrin
un2689
alpha-chlorohydrine
monochlorhydrin
3-chloropropanediol
caswell no. 214a
(+/-)-3-chloro-1,2-propanediol, 98%
alpha-monochlorohydrin
AKOS000121375
NCGC00249201-01
qgs78a3t6p ,
3-mcdp
ec 202-492-4
unii-qgs78a3t6p
u5897
glycerol alpha-monochlorohydrin [un2689] [keep away from food]
4-01-00-02484 (beilstein handbook reference)
C18676
cas-96-24-2
NCGC00256557-01
dtxsid4020664 ,
tox21_302959
dtxcid00664
NCGC00259811-01
tox21_202262
BBL011374
a-monochlorohydrin
a-glycerol chlorohydrin
STL146471
FT-0605055
FT-0605261
(s)-( )-3-chloro-1,2-propanediol
chlorohydrin-
(+/-)-2,3-dihydroxychloropropane
.alpha.-chlorohydrin [mi]
.alpha.-chlorohydrin, (+/-)-
3-chloro-1,2-proandiol
3-chloropropylene glycol. epibloc (pestcon)
dl-.alpha.-chlorohydrin
ekorod a
glycerin .alpha.-monochlorhydrin
(+/-)-3-chloro-1,2-propanediol
.alpha.-monochlorohydrin
AKOS016370740
SCHEMBL19213
3-chloro-1,2-dihydroxy-n-propane
3-chloro-1,2-propan-diol
3-chloro-1,2-propandiol
3-chloro-1,2-propane-diol
3-chloro1,2-propanediol
3-chloro-1,2-propane diol
racemic 3-chloro-1,2-propanediol
.beta.,.beta.'-dihydroxyisopropyl chloride
3-chloropropandiol-(1,2)
glycerol .alpha.-chlorohydrin
un 2689
(.+/-.)-2,3-dihydroxychloropropane
glyceryl .alpha.-chlorohydrin
glycerol-.alpha.-monochlorohydrin
.alpha.-monochlorohydrine
CHEMBL3185949
mfcd00004712
(+/-)-3-chloro-1,2-propanediol, purum, >=98.0% (gc)
(+/-)-3-chloro-1,2-propanediol, analytical standard
EN300-21131
glycerol a-monochlorohydrin
3-dichloro-1,2-propanediol
glycerin alpha -monochlorhydrin
alpha-glycerol chlorohydrin
glycerol-alpha -monochlorohydrin
glyceryl alpha -chlorohydrin
glycerol alpha -chlorohydrin
VS-02932
Q223066
(+/-)-alpha-chlorohydrin
3-chloro-1,2-propanediol 100 microg/ml in acetonitrile
AMY21866
BCP31835
3-chloropropane-1,2-diol;chlorodeoxyglycerol
(s)-acetylthio-3-phenylpropionicacid
SB44720
3-chloro-1,2-propanediol 100 microg/ml in ethyl acetate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"alpha-Chlorohydrin (ACH) was administered to rats in a short-term male reproductive toxicity study to examine the usefulness of the method and to provide reference data with a substance that is known to elicit adverse effects on both sperm production and sperm quality within or following a 2-week treatment period."( Utilization of a short-term male reproductive toxicity study design to examine effects of alpha-chlorohydrin (3-chloro-1,2-propanediol).
Fisher, LF; Hoffman, WP; Hoyt, JA; Seyler, DE; Swisher, DK,
)
1.8
" The results from this study indicate that m-DNB may have direct toxic effects on brain endothelial cells which lead to loss of barrier function."( Acute energy deprivation syndromes: investigation of m-dinitrobenzene and alpha-chlorohydrin toxicity on immortalized rat brain microvessel endothelial cells.
Abbott, NJ; Chan, MW; Rist, RJ; Romero, IA, 1997
)
0.53
" The literature on the toxic effects of these contraceptive agents was reviewed and was found to be wanting in respect to the rigour of scientific methods applied (impure compounds were used, inappropriate target populations were studied, excessive doses were employed, abstracts were cited from which no full publications subsequently arose)."( A re-appraisal of the post-testicular action and toxicity of chlorinated antifertility compounds.
Cooper, TG; Jones, AR, 1999
)
0.3
" In cultures from untreated animals the primary alcohol, 2,3-dichloropropanol, was not toxic and did not significantly deplete glutathione."( Effect of cyanamide on toxicity and glutathione depletion in rat hepatocyte cultures: differences between two dichloropropanol isomers.
Fry, JR; Hammond, AH, 1999
)
0.3
" An in vitro model was developed to study the direct toxic effects that follow the metabolic activation of chemicals."( A Genetically engineered cell-based system for detecting metabolism-mediated toxicity.
Bull, S; Clothier, R; Coecke, S; Langezaal, I,
)
0.13
" We suggest that 1,3-DCA could be embryotoxic at doses that do not cause adverse maternal hepatic damage."( The relative embryotoxicity of 1,3-dichloro-2-propanol on primary chick embryonic cells.
Clothier, RH; L'Huillier, N; Pratten, MK, 2002
)
0.31
" 1) A marked elevation of serum AST and ALT with massive necrosis of the liver was noted in the 1/2 x, the 1 x and 2 x LD50 (0."( [Toxicity of dichloropropanols].
Fueta, Y; Imai, H; Katoh, T; Kohshi, K; Kuroda, Y; Nakao, H, 2002
)
0.31
"The LD50 (95% CI) of R, S and (R,S)-3-MCPD were 290."( [Study on acute toxicity of R, S and (R,S)-3-monchloropropane-1,2-diol].
Qian, G; Yin, L; Zhang, G; Zhang, H, 2007
)
0.34
" LD50 (median lethal dose) value of 3-MCPD 1-monopalmitate was determined 2676."( Acute oral toxicity of 3-MCPD mono- and di-palmitic esters in Swiss mice and their cytotoxicity in NRK-52E rat kidney cells.
Gao, BY; Jiang, YR; Liu, M; Luo, W; Ma, AN; Qin, F; Shi, HM; Wu, PP; Xu, XB; Yu, LL, 2012
)
0.38
" The LD50 value of 3-MCPD dipalmitate was determined to be 1780 mg/kg body weight (bw) for Wistar rats."( The toxicity of 3-chloropropane-1,2-dipalmitate in Wistar rats and a metabonomics analysis of rat urine by ultra-performance liquid chromatography-mass spectrometry.
Du, X; Li, J; Shi, W; Sun, C; Wang, M; Wang, S, 2013
)
0.39
"The food contaminants 3-chloro-1,2-propanediol (3-MCPD) and 3-MCPD fatty acid esters have attracted considerable attention in the past few years due to their toxic properties and their occurrence in numerous foods."( 2-Chloro-1,3-propanediol (2-MCPD) and its fatty acid esters: cytotoxicity, metabolism, and transport by human intestinal Caco-2 cells.
Buhrke, T; Frenzel, F; Kuhlmann, J; Lampen, A, 2015
)
0.42
" Toxic properties of 3-MCPD in kidney and testis have extensively been characterized."( Comparative proteomic analysis of 2-MCPD- and 3-MCPD-induced heart toxicity in the rat.
Braeuning, A; Buhrke, T; Frenzel, F; Lampen, A; Oberemm, A; Schultrich, K, 2017
)
0.46
"3-Monochloropropane-1,2-diol (3-MCPD), as a heat-induced food process contaminant, possesses strongly toxic effect on kidney."( Nephrotoxicity evaluation of 3-monochloropropane-1,2-diol exposure in Sprague-Dawley rats using data-independent acquisition-based quantitative proteomics analysis.
Jin, C; Liu, Q; Luo, R; Min, F; Peng, X; Sun, D; Zhong, Y, 2022
)
0.72

Compound-Compound Interactions

ExcerptReferenceRelevance
"This study proposes a method for identifying 1,3-dichloro-2-propanol and 3-chloro-1,2-propandiol in aqueous matrices by using headspace on-fiber derivatization following solid-phase microextraction combined with gas chromatography-mass spectrometry."( Determination of 1,3-dichloro-2-propanol and 3-chloro-1,2-propandiol in soy sauce by headspace derivatization solid-phase microextraction combined with gas chromatography-mass spectrometry.
Chiu, TC; Dou, J; Lee, MR, 2007
)
0.34

Bioavailability

ExcerptReferenceRelevance
" Although potency was retained, acute oral toxicity was greatly reduced, due to a combination of factors - the esters were poorly absorbed in high dosage whilst relatively slow breakdown permitted effective levels to be attained on epididymal spermatozoa."( Antifertility and toxicological studies with aromatic esters of alpha-chlorohydrin in male rats.
Jackson, H; Rooney, FR, 1980
)
0.5
" 3-MCPD mono- and diesters, is important to assess the contribution of foods to the bioavailability of 3-MCPD."( Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD.
Scanlan, FP; Seefelder, W; Stadler, RH; Studer, A; Varga, N; Williamson, G, 2008
)
0.35
" However, the real oral bioavailability may be lower."( Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acid esters in food.
Abraham, K; Appel, KE; Bakhiya, N; Gürtler, R; Lampen, A, 2011
)
0.37
"In order to quantify the relative oral bioavailability of 3-chloropropane-1,2-diol (3-MCPD) from 3-MCPD fatty acid diesters in vivo, 1,2-dipalmitoyl-3-chloropropane-1,2-diol (3-MCPD diester) and 3-MCPD were orally applied to rats in equimolar doses."( Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats.
Abraham, K; Apel, E; Appel, KE; Berger-Preiss, E; Creutzenberg, O; Gerling, S; Lampen, A; Mielke, H, 2013
)
0.39

Dosage Studied

Male rats dosed orally with S alpha-chlorohydrin (3-25 mg/kg/day) became much less fertile than controls. Those dosed with R alpha- chlorohydrin did not.

ExcerptRelevanceReference
"Male Wistar Strain rats of known fertility were given subcutaneous dosage of three drugs, alpha-chlorohydrin, amino-alpha-chlorohydrin, and busulphan alone or in combination for a period of thirty days."( Agonistic properties of low doses of antifertility compounds in male rats.
Hafez, ES; Shandilya, LN; Snydle, FE, 1979
)
0.48
" Although testosterone and other androgens suppress spermatogenesis in man, the feasibility of their use for contraception depends on the establishment of a dosage and mode of adminstration that provide antispermatogenic action without causing more general metabolic alterations."( Target sites for suppressing fertility in the male.
Prasad, MR; Rajalakshmi, M, 1976
)
0.26
" Male rats dosed orally with S alpha-chlorohydrin (3-25 mg/kg/day) became much less fertile than controls but those dosed with R alpha-chlorohydrin (13 mg/kg/day) did not."( Effects of the optical isomers of alpha-chlorohydrin on glycolysis by ram testicular spermatozoa and the fertility of male rats.
Ford, WC; Harrison, A; Waites, GM, 1977
)
0.82
" Significant changes in endpoints describing sperm swimming vigor (curvilinear velocity and straight-line velocity) and pattern (linearity and amplitude of lateral head displacement) were observed for rats dosed with each agent when evaluations included mean values and other statistical parameters (i."( Effects of three male reproductive toxicants on rat cauda epididymal sperm motion.
McCarthy, H; Smith, MK; Tocco, DR; Toth, GP; Wang, SR, 1992
)
0.28
" In this study, male Fischer 344 rats were dosed (6 mg/kg) orally with [2-14C]ECH (98% radiochemically pure) as an aqueous solution and killed after 3 days."( Disposition and metabolism of [2-14C]epichlorohydrin after oral administration to rats.
Beatty, PW; Dzidic, I; Gingell, R; Mitschke, HR; Page, AC; Sawin, VL,
)
0.13
"The present study was undertaken to determine the effects of alpha-chlorohydrin at a dosage of 50, 100 or 150 mg/kg body weight and were killed 2 or 10 days later."( Effects of alpha-chlorohydrin on the reproductive organs of the male bandicoot rat (Bandicota bengalensis).
Shinha Hikim, AP,
)
0.76
" Although potency was retained, acute oral toxicity was greatly reduced, due to a combination of factors - the esters were poorly absorbed in high dosage whilst relatively slow breakdown permitted effective levels to be attained on epididymal spermatozoa."( Antifertility and toxicological studies with aromatic esters of alpha-chlorohydrin in male rats.
Jackson, H; Rooney, FR, 1980
)
0.5
" Further comparisons of the validity of 4 or 9 weeks treatment require the testing of other compounds with different targets/mechanism of actions, as well as evaluation of dose-response relationships."( Improved risk assessment by screening sperm parameters.
Plassmann, S; Urwyler, H, 2001
)
0.31
" The pregnancy rates have been very low to zero depending on the dosage and the mode of administration."( New developments in contraceptive agents.
Hofmann, F, 1971
)
0.25
"3-MCPD was administrated with a single oral dosage of 75 mg/kg BW to each rat."( [Study on the absorption, distribution and excretion of 3-chloro-1,2-propandiol in rats].
Luo, RC; Xiao, Y; Zhang, Z; Zhou, Y, 2003
)
0.32
" Currently, adequate dose-response relationships and mechanistic information regarding carcinogenicity of acrylamide are lacking."( Human health risk assessment of processing-related compounds in food.
Tritscher, AM, 2004
)
0.32
" Additionally, 3-MCPD (5 mg/kg) significantly reduced sperm motility, copulation, fertility indices, and the number of live fetuses showed steep dose-response curves."( Mechanism of antifertility in male rats treated with 3-monochloro-1,2-propanediol (3-MCPD).
Chae, SY; Choi, KS; Choi, YW; Da Lee, R; Kim, SS; Kwack, SJ; Lee, BM; Lim, KJ; Park, KL; Rhee, GS; Seok, JH; Won, YH, 2004
)
0.32
" Benchmark dose analysis of the dose-response data for renal tubular hyperplasia in male and female rats exposed to 3-MCPD in drinking water for 2 years was conducted."( Toxicity value for 3-monochloropropane-1,2-diol using a benchmark dose methodology.
Hwang, M; Jang, DD; Kim, J; Yoo, TM; Yoon, E, 2009
)
0.35
" One such tool is the International Life Sciences Institute (ILSI) Key Events Dose-Response Framework (KEDRF)."( Application of the International Life Sciences Institute Key Events Dose-Response Framework to food contaminants.
Fenner-Crisp, PA, 2012
)
0.38
" Enrichment and dose-response showed a linear relationship to 3-MCPD ester formation and indicated that the sphingolipid-based organochlorine compounds are the most active precursors of 3-MCPD esters."( Natural Organochlorines as Precursors of 3-Monochloropropanediol Esters in Vegetable Oils.
Appleton, DR; Lai, OM; Md Noor, A; Md Zain, MZB; Neoh, BK; Ng, TLM; Saparin, N; Tan, CP; Teh, HF; Tiong, SH, 2018
)
0.48
" The combination of high dosage phosphoric acid during degumming with the use of acid activated bleaching earth eliminated almost all glycidyl esters during refining."( New Insights on Degumming and Bleaching Process Parameters on The Formation of 3-Monochloropropane-1,2-Diol Esters and Glycidyl Esters in Refined, Bleached, Deodorized Palm Oil.
Abas, F; Khor, YP; Lai, OM; Muhamad, H; Nehdi, IA; Sim, BI; Tan, CP; Yeoh, CB, 2018
)
0.48
" The motivation, development, and assessment of new methods for risk assessment is facilitated by the availability of a set of experimental studies that span a range of dose-response patterns that are observed in practice."( Quantal Risk Assessment Database: A Database for Exploring Patterns in Quantal Dose-Response Data in Risk Assessment and its Application to Develop Priors for Bayesian Dose-Response Analysis.
Bailer, AJ; Piegorsch, WW; Wheeler, MW, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
chloropropane-1,2-diolAn organochlorine compound that is propane-1,2-diol substituted by a chlorine atom at unspecified position.
[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]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.48980.000229.305416,493.5996AID743075
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency61.13060.000627.21521,122.0200AID743202
Cellular tumor antigen p53Homo sapiens (human)Potency0.96790.002319.595674.0614AID651631
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (124)

Processvia Protein(s)Taxonomy
negative regulation of cell population proliferationCellular tumor antigen p53Homo sapiens (human)
regulation of cell cycleCellular tumor antigen p53Homo sapiens (human)
regulation of cell cycle G2/M phase transitionCellular tumor antigen p53Homo sapiens (human)
DNA damage responseCellular tumor antigen p53Homo sapiens (human)
ER overload responseCellular tumor antigen p53Homo sapiens (human)
cellular response to glucose starvationCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
regulation of apoptotic processCellular tumor antigen p53Homo sapiens (human)
positive regulation of transcription by RNA polymerase IICellular tumor antigen p53Homo sapiens (human)
positive regulation of miRNA transcriptionCellular tumor antigen p53Homo sapiens (human)
negative regulation of transcription by RNA polymerase IICellular tumor antigen p53Homo sapiens (human)
mitophagyCellular tumor antigen p53Homo sapiens (human)
in utero embryonic developmentCellular tumor antigen p53Homo sapiens (human)
somitogenesisCellular tumor antigen p53Homo sapiens (human)
release of cytochrome c from mitochondriaCellular tumor antigen p53Homo sapiens (human)
hematopoietic progenitor cell differentiationCellular tumor antigen p53Homo sapiens (human)
T cell proliferation involved in immune responseCellular tumor antigen p53Homo sapiens (human)
B cell lineage commitmentCellular tumor antigen p53Homo sapiens (human)
T cell lineage commitmentCellular tumor antigen p53Homo sapiens (human)
response to ischemiaCellular tumor antigen p53Homo sapiens (human)
nucleotide-excision repairCellular tumor antigen p53Homo sapiens (human)
double-strand break repairCellular tumor antigen p53Homo sapiens (human)
regulation of DNA-templated transcriptionCellular tumor antigen p53Homo sapiens (human)
regulation of transcription by RNA polymerase IICellular tumor antigen p53Homo sapiens (human)
protein import into nucleusCellular tumor antigen p53Homo sapiens (human)
autophagyCellular tumor antigen p53Homo sapiens (human)
DNA damage responseCellular tumor antigen p53Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrestCellular tumor antigen p53Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediatorCellular tumor antigen p53Homo sapiens (human)
transforming growth factor beta receptor signaling pathwayCellular tumor antigen p53Homo sapiens (human)
Ras protein signal transductionCellular tumor antigen p53Homo sapiens (human)
gastrulationCellular tumor antigen p53Homo sapiens (human)
neuroblast proliferationCellular tumor antigen p53Homo sapiens (human)
negative regulation of neuroblast proliferationCellular tumor antigen p53Homo sapiens (human)
protein localizationCellular tumor antigen p53Homo sapiens (human)
negative regulation of DNA replicationCellular tumor antigen p53Homo sapiens (human)
negative regulation of cell population proliferationCellular tumor antigen p53Homo sapiens (human)
determination of adult lifespanCellular tumor antigen p53Homo sapiens (human)
mRNA transcriptionCellular tumor antigen p53Homo sapiens (human)
rRNA transcriptionCellular tumor antigen p53Homo sapiens (human)
response to salt stressCellular tumor antigen p53Homo sapiens (human)
response to inorganic substanceCellular tumor antigen p53Homo sapiens (human)
response to X-rayCellular tumor antigen p53Homo sapiens (human)
response to gamma radiationCellular tumor antigen p53Homo sapiens (human)
positive regulation of gene expressionCellular tumor antigen p53Homo sapiens (human)
cardiac muscle cell apoptotic processCellular tumor antigen p53Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic processCellular tumor antigen p53Homo sapiens (human)
glial cell proliferationCellular tumor antigen p53Homo sapiens (human)
viral processCellular tumor antigen p53Homo sapiens (human)
glucose catabolic process to lactate via pyruvateCellular tumor antigen p53Homo sapiens (human)
cerebellum developmentCellular tumor antigen p53Homo sapiens (human)
negative regulation of cell growthCellular tumor antigen p53Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayCellular tumor antigen p53Homo sapiens (human)
mitotic G1 DNA damage checkpoint signalingCellular tumor antigen p53Homo sapiens (human)
negative regulation of telomere maintenance via telomeraseCellular tumor antigen p53Homo sapiens (human)
T cell differentiation in thymusCellular tumor antigen p53Homo sapiens (human)
tumor necrosis factor-mediated signaling pathwayCellular tumor antigen p53Homo sapiens (human)
regulation of tissue remodelingCellular tumor antigen p53Homo sapiens (human)
cellular response to UVCellular tumor antigen p53Homo sapiens (human)
multicellular organism growthCellular tumor antigen p53Homo sapiens (human)
positive regulation of mitochondrial membrane permeabilityCellular tumor antigen p53Homo sapiens (human)
cellular response to glucose starvationCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
positive regulation of apoptotic processCellular tumor antigen p53Homo sapiens (human)
negative regulation of apoptotic processCellular tumor antigen p53Homo sapiens (human)
entrainment of circadian clock by photoperiodCellular tumor antigen p53Homo sapiens (human)
mitochondrial DNA repairCellular tumor antigen p53Homo sapiens (human)
regulation of DNA damage response, signal transduction by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
positive regulation of neuron apoptotic processCellular tumor antigen p53Homo sapiens (human)
transcription initiation-coupled chromatin remodelingCellular tumor antigen p53Homo sapiens (human)
negative regulation of proteolysisCellular tumor antigen p53Homo sapiens (human)
negative regulation of DNA-templated transcriptionCellular tumor antigen p53Homo sapiens (human)
positive regulation of DNA-templated transcriptionCellular tumor antigen p53Homo sapiens (human)
positive regulation of RNA polymerase II transcription preinitiation complex assemblyCellular tumor antigen p53Homo sapiens (human)
positive regulation of transcription by RNA polymerase IICellular tumor antigen p53Homo sapiens (human)
response to antibioticCellular tumor antigen p53Homo sapiens (human)
fibroblast proliferationCellular tumor antigen p53Homo sapiens (human)
negative regulation of fibroblast proliferationCellular tumor antigen p53Homo sapiens (human)
circadian behaviorCellular tumor antigen p53Homo sapiens (human)
bone marrow developmentCellular tumor antigen p53Homo sapiens (human)
embryonic organ developmentCellular tumor antigen p53Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationCellular tumor antigen p53Homo sapiens (human)
protein stabilizationCellular tumor antigen p53Homo sapiens (human)
negative regulation of helicase activityCellular tumor antigen p53Homo sapiens (human)
protein tetramerizationCellular tumor antigen p53Homo sapiens (human)
chromosome organizationCellular tumor antigen p53Homo sapiens (human)
neuron apoptotic processCellular tumor antigen p53Homo sapiens (human)
regulation of cell cycleCellular tumor antigen p53Homo sapiens (human)
hematopoietic stem cell differentiationCellular tumor antigen p53Homo sapiens (human)
negative regulation of glial cell proliferationCellular tumor antigen p53Homo sapiens (human)
type II interferon-mediated signaling pathwayCellular tumor antigen p53Homo sapiens (human)
cardiac septum morphogenesisCellular tumor antigen p53Homo sapiens (human)
positive regulation of programmed necrotic cell deathCellular tumor antigen p53Homo sapiens (human)
protein-containing complex assemblyCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to endoplasmic reticulum stressCellular tumor antigen p53Homo sapiens (human)
thymocyte apoptotic processCellular tumor antigen p53Homo sapiens (human)
positive regulation of thymocyte apoptotic processCellular tumor antigen p53Homo sapiens (human)
necroptotic processCellular tumor antigen p53Homo sapiens (human)
cellular response to hypoxiaCellular tumor antigen p53Homo sapiens (human)
cellular response to xenobiotic stimulusCellular tumor antigen p53Homo sapiens (human)
cellular response to ionizing radiationCellular tumor antigen p53Homo sapiens (human)
cellular response to gamma radiationCellular tumor antigen p53Homo sapiens (human)
cellular response to UV-CCellular tumor antigen p53Homo sapiens (human)
stem cell proliferationCellular tumor antigen p53Homo sapiens (human)
signal transduction by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathway by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
reactive oxygen species metabolic processCellular tumor antigen p53Homo sapiens (human)
cellular response to actinomycin DCellular tumor antigen p53Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondriaCellular tumor antigen p53Homo sapiens (human)
cellular senescenceCellular tumor antigen p53Homo sapiens (human)
replicative senescenceCellular tumor antigen p53Homo sapiens (human)
oxidative stress-induced premature senescenceCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathwayCellular tumor antigen p53Homo sapiens (human)
oligodendrocyte apoptotic processCellular tumor antigen p53Homo sapiens (human)
positive regulation of execution phase of apoptosisCellular tumor antigen p53Homo sapiens (human)
negative regulation of mitophagyCellular tumor antigen p53Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic processCellular tumor antigen p53Homo sapiens (human)
regulation of intrinsic apoptotic signaling pathway by p53 class mediatorCellular tumor antigen p53Homo sapiens (human)
positive regulation of miRNA transcriptionCellular tumor antigen p53Homo sapiens (human)
negative regulation of G1 to G0 transitionCellular tumor antigen p53Homo sapiens (human)
negative regulation of miRNA processingCellular tumor antigen p53Homo sapiens (human)
negative regulation of glucose catabolic process to lactate via pyruvateCellular tumor antigen p53Homo sapiens (human)
negative regulation of pentose-phosphate shuntCellular tumor antigen p53Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to hypoxiaCellular tumor antigen p53Homo sapiens (human)
regulation of fibroblast apoptotic processCellular tumor antigen p53Homo sapiens (human)
negative regulation of reactive oxygen species metabolic processCellular tumor antigen p53Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processCellular tumor antigen p53Homo sapiens (human)
negative regulation of stem cell proliferationCellular tumor antigen p53Homo sapiens (human)
positive regulation of cellular senescenceCellular tumor antigen p53Homo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathwayCellular tumor antigen p53Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (34)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingCellular tumor antigen p53Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingCellular tumor antigen p53Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificCellular tumor antigen p53Homo sapiens (human)
cis-regulatory region sequence-specific DNA bindingCellular tumor antigen p53Homo sapiens (human)
core promoter sequence-specific DNA bindingCellular tumor antigen p53Homo sapiens (human)
TFIID-class transcription factor complex bindingCellular tumor antigen p53Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificCellular tumor antigen p53Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificCellular tumor antigen p53Homo sapiens (human)
protease bindingCellular tumor antigen p53Homo sapiens (human)
p53 bindingCellular tumor antigen p53Homo sapiens (human)
DNA bindingCellular tumor antigen p53Homo sapiens (human)
chromatin bindingCellular tumor antigen p53Homo sapiens (human)
DNA-binding transcription factor activityCellular tumor antigen p53Homo sapiens (human)
mRNA 3'-UTR bindingCellular tumor antigen p53Homo sapiens (human)
copper ion bindingCellular tumor antigen p53Homo sapiens (human)
protein bindingCellular tumor antigen p53Homo sapiens (human)
zinc ion bindingCellular tumor antigen p53Homo sapiens (human)
enzyme bindingCellular tumor antigen p53Homo sapiens (human)
receptor tyrosine kinase bindingCellular tumor antigen p53Homo sapiens (human)
ubiquitin protein ligase bindingCellular tumor antigen p53Homo sapiens (human)
histone deacetylase regulator activityCellular tumor antigen p53Homo sapiens (human)
ATP-dependent DNA/DNA annealing activityCellular tumor antigen p53Homo sapiens (human)
identical protein bindingCellular tumor antigen p53Homo sapiens (human)
histone deacetylase bindingCellular tumor antigen p53Homo sapiens (human)
protein heterodimerization activityCellular tumor antigen p53Homo sapiens (human)
protein-folding chaperone bindingCellular tumor antigen p53Homo sapiens (human)
protein phosphatase 2A bindingCellular tumor antigen p53Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingCellular tumor antigen p53Homo sapiens (human)
14-3-3 protein bindingCellular tumor antigen p53Homo sapiens (human)
MDM2/MDM4 family protein bindingCellular tumor antigen p53Homo sapiens (human)
disordered domain specific bindingCellular tumor antigen p53Homo sapiens (human)
general transcription initiation factor bindingCellular tumor antigen p53Homo sapiens (human)
molecular function activator activityCellular tumor antigen p53Homo sapiens (human)
promoter-specific chromatin bindingCellular tumor antigen p53Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
nuclear bodyCellular tumor antigen p53Homo sapiens (human)
nucleusCellular tumor antigen p53Homo sapiens (human)
nucleoplasmCellular tumor antigen p53Homo sapiens (human)
replication forkCellular tumor antigen p53Homo sapiens (human)
nucleolusCellular tumor antigen p53Homo sapiens (human)
cytoplasmCellular tumor antigen p53Homo sapiens (human)
mitochondrionCellular tumor antigen p53Homo sapiens (human)
mitochondrial matrixCellular tumor antigen p53Homo sapiens (human)
endoplasmic reticulumCellular tumor antigen p53Homo sapiens (human)
centrosomeCellular tumor antigen p53Homo sapiens (human)
cytosolCellular tumor antigen p53Homo sapiens (human)
nuclear matrixCellular tumor antigen p53Homo sapiens (human)
PML bodyCellular tumor antigen p53Homo sapiens (human)
transcription repressor complexCellular tumor antigen p53Homo sapiens (human)
site of double-strand breakCellular tumor antigen p53Homo sapiens (human)
germ cell nucleusCellular tumor antigen p53Homo sapiens (human)
chromatinCellular tumor antigen p53Homo sapiens (human)
transcription regulator complexCellular tumor antigen p53Homo sapiens (human)
protein-containing complexCellular tumor antigen p53Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1149641Toxicity in ip dosed BDF1 mouse1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
3-Fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone) and some esters. Syntheses and effects in BDF mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (508)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990125 (24.61)18.7374
1990's38 (7.48)18.2507
2000's82 (16.14)29.6817
2010's158 (31.10)24.3611
2020's105 (20.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.90

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 Index17.90 (24.57)
Research Supply Index6.29 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.37%)5.53%
Reviews28 (5.20%)6.00%
Case Studies2 (0.37%)4.05%
Observational0 (0.00%)0.25%
Other506 (94.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]