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Hypotaurine
Names
IUPAC name
2-Aminoethanesulfinic acid
Identifiers
ChEBI
ChemSpider
ECHA InfoCard
100.155.825
KEGG
UNII
InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
Y Key: VVIUBCNYACGLLV-UHFFFAOYSA-N
Y InChI=1/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
Key: VVIUBCNYACGLLV-UHFFFAOYAM
Properties
C2 H7 NO2 S
Molar mass
109.15 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Hypotaurine is a sulfinic acid that is an intermediate in the biosynthesis of taurine . Like taurine, it also acts as an endogenous neurotransmitter via action on the glycine receptors .[ 1]
Hypotaurine is derived from cysteine (and homocysteine ). In mammals, the biosynthesis of hypotaurine from cysteine occurs in the pancreas. In the cysteine sulfinic acid pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase . Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine . Hypotaurine is enzymatically oxidized to yield taurine by hypotaurine dehydrogenase .[ 2]
Hypotaurine (3) is an intermediate in the conversion of cysteine (1) to taurine (4).
References
^ Kalir, Asher; Kalir, Henry H. "Biological activity of sulfinic acid derivatives" in Chemistry of Sulphinic Acids, Esters Their Derivatives Edited by Patai, Saul. Wiley, New York, 1990, pp. 665.
^ Sumizu K (1962). "Oxidation of hypotaurine in rat liver". Biochim. Biophys. Acta . 63 : 210–212. doi :10.1016/0006-3002(62)90357-8 . PMID 13979247 .
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P) , tribromoethanol , trichloroethanol , trifluoroethanol )
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g., pentobarbital , sodium thiopental )
Chlormethiazole
D12-116
Dihydropyridines (e.g., nicardipine )
Etomidate
Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )
Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )
Xenon
Zinc
Antagonists: 2-Aminostrychnine
2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
Cacotheline
Caffeine
Colchicine
Colubrine
Cyanotriphenylborate
Dendrobine
Diaboline
Endocannabinoids (e.g., 2-AG , anandamide (AEA) )
Gaboxadol (THIP)
Gelsemine
iso-THAZ
Isobutyric acid
Isonipecotic acid
Isostrychnine
Laudanosine
N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid
Pitrazepin
Pseudostrychnine
Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )
RU-5135
Sinomenine
Strychnine
Thiocolchicoside
Tutin
Negative modulators: Amiloride
Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )
Furosemide
Genistein
Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))
Imipramine
NBQX
Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )
Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )
Picrotoxin (i.e., picrotin and picrotoxinin )
PMBA
Riluzole
Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )
Verapamil
Zinc
NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2