propiolic acid profile

Propiolic acid, also known as 3-propynoic acid, is a highly reactive organic compound with a triple bond between the second and third carbon atoms. It is a colorless liquid with a pungent odor.

**Synthesis:** Propiolic acid can be synthesized through various methods, including:
* **Reaction of acetylene with carbon dioxide in the presence of a catalyst:** This is a common method for industrial-scale production.
* **Dehydration of tartaric acid:** This method involves heating tartaric acid in the presence of a dehydrating agent.
* **Reaction of propiolic acid derivatives with strong acids:** This method involves the use of propiolic acid esters or amides as starting materials.

**Effects:** Propiolic acid is a strong acid with a pKa of 1.8. It is also a highly reactive compound that can undergo various reactions, including:
* **Nucleophilic addition:** The triple bond in propiolic acid can react with nucleophiles, such as alcohols and amines, to form adducts.
* **Cycloaddition:** Propiolic acid can participate in cycloaddition reactions with dienes, forming cyclic compounds.
* **Polymerization:** Propiolic acid can polymerize under certain conditions to form polypropargyl polymers.

**Importance and Research:** Propiolic acid is of significant interest in various fields, including:
* **Organic synthesis:** It is a versatile building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and polymers.
* **Materials science:** Propiolic acid and its derivatives are used in the production of polymers, resins, and adhesives with unique properties.
* **Medicinal chemistry:** Some derivatives of propiolic acid have shown potential as antibacterial, antifungal, and anticancer agents.

**Why it is studied:**
* **Highly reactive nature:** Its highly reactive triple bond makes it a valuable synthetic intermediate for various reactions.
* **Potential applications:** Propiolic acid and its derivatives have potential applications in a wide range of fields, including materials science, medicinal chemistry, and organic synthesis.
* **Understanding its chemistry:** Research on propiolic acid helps to better understand its chemical properties and reactivity, which is crucial for its safe and efficient use in various applications.'

propiolic acid: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond. [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]

ID Source	ID
PubMed CID	10110
CHEMBL ID	1213530
CHEBI ID	33199
MeSH ID	M0057897

Synonym
CHEMBL1213530
hc#ccooh
propinsaeure
propiolsaeure
CHEBI:33199 ,
prop-2-ynoic acid
propinic acid
hc.equiv.ccooh
nsc 16152
einecs 207-437-8
propynoic acid
2-propynoic acid
propargylic acid
nsc-16152
nsc16152
carboxyacetylene
acetylenecarboxylic acid
propiolic acid
471-25-0
C00804
propiolic acid, 95%
P0497
AKOS000121542
BBL011346
STL146436
p2qw39g9lz ,
hsdb 7857
unii-p2qw39g9lz
2-propyne-1-carboxylic acid
acetylenemonocarboxylic acid
propiolic acid [mi]
S6108
acetylene carboxylic acid
DTXSID6060050
STR03210
hc.$.ccooh
mfcd00004360
F2191-0185
propiolic acid, technical, >=95% (t)
BCP18740
Q257590
AMY7000
F10329
26969-44-8
EN300-21202
Z104493798

Excerpt	Reference	Relevance
" In our continuing efforts to identify small molecule alpha(V)beta(3) and alpha(V)beta(5) dual antagonists, we recently reported indoles 2-4 as potent and selective alpha(V)beta(3)/alpha(V)beta(5) antagonists with good oral bioavailability profile."	( Novel potent and selective alphavbeta3/alphavbeta5 integrin dual antagonists with reduced binding affinity for human serum albumin. Chaikin, M; Crysler, C; Lattanze, J; Leonard, K; Manthey, CL; Marugán, JJ; Pan, W; Raboisson, P; Tomczuk, BE, 2006)	0.33

Role	Description
xenobiotic metabolite	Any metabolite produced by metabolism of a xenobiotic compound.
[role 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]

Class	Description
acetylenic fatty acid	Any unsaturated fatty acid containing at least one triple bond in the carbon chain framework.
monounsaturated fatty acid	Any fatty acid with one double or triple bond in the fatty acid chain and singly bonded carbon atoms in the rest of the chain. MUFAs have positive effects on the cardiovascular system, and in diabetes treatment.
short-chain fatty acid	An aliphatic monocarboxylic acid with a chain length of less than C6. If any non-hydrocarbon substituent is present, the compound is not normally regarded as a short-chain fatty acid.
terminal acetylenic compound	An acetylenic compound which a carbon of the C#C moiety is attached to a hydrogen atom.
alpha,beta-unsaturated monocarboxylic acid	A monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
[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]

Pathway	Proteins	Compounds
Propanoate metabolism ( Propanoate metabolism )	22	22
NAD+ + 2-Propyn-1-al + H2O = NADH + Propiolic acid ( Propanoate metabolism )	7	4

Assay ID	Title	Year	Journal	Article
AID1432754	Time-dependent Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432755	Competitive inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production preincubated with enzyme followed by addition of varying levels of urea as substrate measured for 120 mins by Lineweaver-Burk plot analysis	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID498775	Toxicity in po dosed mouse	2009	Nature chemical biology, Jul, Volume: 5, Issue:7	Identification of the toxic trigger in mushroom poisoning.
AID1432760	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring steady state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432756	Reversible inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring recovery of enzyme activity at 10 times IC50 preincubated for 60 mins followed by 100-fold dilution in to PBS containing urea as subst	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432759	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring initial state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432751	Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate measured for 120 mins by phenol-hypochlorite method	2017	Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6	Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (2.86)	18.7374
1990's	0 (0.00)	18.2507
2000's	28 (40.00)	29.6817
2010's	37 (52.86)	24.3611
2020's	3 (4.29)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (4.23%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	68 (95.77%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.44	2	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.08	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
benzaldehyde [no description available]	2.05	1	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.44	2	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.08	1	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	3.15	5	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	4.65	8	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
2-butynedioic acid 2-butynedioic acid: RN given refers to parent cpd. butynedioic acid : An acetylenic compound that is acetylene in which the hydrogens are replaced by carboxy groups.	2.49	2	acetylenic compound; C4-dicarboxylic acid
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.08	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.03	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.01	1	metal allergen; nickel group element atom	epitope; micronutrient
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.08	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.05	1	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	2.43	2	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.08	1	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
acetohydroxamic acid acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.	2.15	1	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	2.4	2	alpha,beta-unsaturated monocarboxylic acid
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.03	1	benzimidazole; polycyclic heteroarene
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.8	3	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
aniline [no description available]	7.05	1	anilines; primary arylamine
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.4	2	alpha,beta-unsaturated monocarboxylic acid	metabolite
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.08	1	butan-4-olide	metabolite; neurotoxin
4-anisidine 4-anisidine: RN given refers to parent cpd. p-anisidine : A substituted aniline that is aniline in which the hydrogen para to the amino group has been replaced by a methoxy group. It is used as a reagent for the detection of oxidation products such as aldehydes and ketones in fats and oils.	2.11	1	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.05	1	phenylenediamine	allergen; dye; hapten; reagent
3-hydroxybutanal [no description available]	2.03	1
ethyl formate ethyl formate : A formate ester resulting from the formal condensation of formic acid with ethanol.. ethoxycarbonyl group : An organyl group of formula -COOEt.	2.07	1	ethyl ester; formate ester	fumigant; plant metabolite
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.07	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
ethyl vanillin ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.	2.07	1	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent
triethylamine [no description available]	2.03	1	tertiary amine
benzil benzil: structure. benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.	2.1	1	alpha-diketone; aromatic ketone
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.47	2	monohydroxypyridine	plant metabolite
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	2.74	3	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.03	1	adamantanes; polycyclic alkane
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.08	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
hydrazine diamine : Any polyamine that contains two amino groups.	2.5	2	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
lumazine lumazine: structure. 2,4-dihydroxypteridine : Any dihydroxypteridine in which the two hydroxy substituents are located at positions 2 and 4.. lumazine : A 2,4-dihydroxypteridine.	2.43	2	2,4-dihydroxypteridine
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.03	1	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
acetylenedicarboxylic acid dimethyl ester acetylenedicarboxylic acid dimethyl ester: inhibitor of oxidative phosphorylation	2.15	1
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.15	1	alicyclic ketone; enone	Hsp70 inducer
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.15	1	cyclohexenone
phenylglyoxal [no description available]	2.1	1	phenylacetaldehydes
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	8.58	8	metal allergen; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	2.05	1	cobalt group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.05	1	copper group element atom; elemental silver	Escherichia coli metabolite
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	8.15	5	copper group element atom; elemental gold
cesium fluoride cesium fluoride: RN given refers to above cpd	2.08	1
fluorides [no description available]	2.08	1	halide anion; monoatomic fluorine
iodine [no description available]	2.1	1	halide anion; monoatomic iodine	human metabolite
3-butenoic acid but-3-enoic acid : That isomer of butenoic acid having the double bond at position C-3.	2.03	1	butenoic acid
alkenes [no description available]	7.48	2
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.06	1	pseudohalide anion	mitochondrial respiratory-chain inhibitor
2-bromoethanesulfonic acid 2-bromoethanesulfonic acid: RN given refers to parent cpd; a methanogenic inhibitor	2.46	2
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.08	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.97	4	1,2,3-triazole
alpha-methylene gamma-butyrolactone alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position.	2.08	1	butan-4-olide	anti-ulcer drug; gastrointestinal drug
2-butynoic acid [no description available]	2.15	1
phenylpropiolic acid phenylpropiolic acid: structure. phenylpropiolic acid : An acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.	2.15	1	acetylenic compound; alpha,beta-unsaturated monocarboxylic acid; benzenes
urazole urazole: structure in first source	2.01	1
ethyl 2-butynoate [no description available]	2.96	4
methylenecyclopropane methylenecyclopropane: structure in first source	2.08	1
coenzyme a [no description available]	1.97	1	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
ethylphenylpropiolate ethylphenylpropiolate: structure	2.15	1
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	3.55	2	carbene; methanediyl
1,4-diamino-2-butyne 1,4-diamino-2-butyne: structure given in first source	7.07	1
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.02	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	2.04	1	carbodiimide
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.1	1	divalent inorganic anion; phosphite ion
aconitic acid trans-aconitic acid : The trans-isomer of aconitic acid.	2.15	1	aconitic acid	fundamental metabolite
maleic acid maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.	2.15	1	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.15	1	cinnamic acid	plant metabolite
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.15	1	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
oxazolidine oxazolidine: structure given in first source	2.08	1	oxazolidine
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.05	1	2-butenoic acid	plant metabolite
dimethyl fumarate [no description available]	2.15	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
ethyl cinnamate ethyl cinnamate: a pine weevil antifeedant; structure in first source	2.15	1	alkyl cinnamate; ethyl ester
diethyl fumarate diethyl fumarate : A dieter obtained by the formal condensation of fumaric acid with ethanol.	2.15	1	diester	metabolite
prolinol prolinol: RN given refers to cpd without isomeric designation; structure. prolinol : An amino alcohol formed by reduction of the amino acid proline.	2.06	1
3-(4-methylbenzoyl)acrylic acid [no description available]	2.15	1	carbonyl compound
3-bromopropanesulfonate [no description available]	2.02	1
dimethyl maleate dimethyl maleate: structure. dimethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with methanol. It is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	2.15	1	diester; maleate ester; methyl ester
andrographolide [no description available]	2.31	1	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.08	1	alkali metal atom
ethyl fumarate [no description available]	2.15	1
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.07	1	cysteinium	fundamental metabolite
beta-escin [no description available]	2.08	1
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.06	1
inosine [no description available]	2.08	1	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
Mushroom Poisoning Poisoning from ingestion of mushrooms, primarily from, but not restricted to, toxic varieties.	2.05	1
Rhabdomyolysis Necrosis or disintegration of skeletal muscle often followed by myoglobinuria.	2.05	1
Infections, Yersinia [description not available]	2.6	1
Diabetes Mellitus, Adult-Onset [description not available]	2.06	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.06	1
Cancer of Ovary [description not available]	2.07	1
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	2.07	1

propiolic acid

Description

Cross-References

Synonyms (46)

Research Excerpts

Bioavailability

Roles (1)

Drug Classes (5)

Pathways (2)

Bioassays (7)

Research

Studies (70)

Market Indicators

Research Demand Index: 48.25

Study Types