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Term:
4-hydroxybutyric acid (CHEBI:30830)
Annotations: Rat: (2) Mouse: (2) Human: (2) Chinchilla: (0) Bonobo: (0) Dog: (0) Squirrel: (0) Pig: (0)
Parent Terms Term With Siblings Child Terms
(2S)-2-[(\{4-[2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl\}carbonyl)amino]-4-(2H-tetrazol-5-yl)butanoic acid 
(2S)-3-methyl-2-((2R,3S)-3-[(methylsulfonyl)amino]-1-\{[2-(pyrrolidin-1-ylmethyl)-1,3-oxazol-4-yl]carbonyl\}pyrrolidin-2-yl)butanoic acid 
(2S,3R)-2-[(3S,6R)-3-amino-6-hydroxy-2-oxopiperidinyl]-3-hydroxybutanoic acid 
(4R)-4-hydroxypentanoic acid +  
(R)-2-hydroxy-4-(hydroxymethylphosphinyl)butyric acid 
(R)-3,4-dihydroxy-2-oxobutanoic acid 
(R)-3-[(R)-3-hydroxybutanoyloxy]butanoic acid 
(R)-3-hydroxy-2-oxo-4-phosphonooxybutanoic acid 
(R)-sarin +   
(R)-thalidomide +   
(S)-2,4-dihydroxy-3-oxobutanoic acid 
(S)-2-acetyl-2-hydroxybutanoic acid 
(S)-2-chloropropanoic acid 
(S)-3,4-dihydroxy-2-oxobutanoic acid 
(S)-amphetamine +   
(S)-nicotine +   
(S)-sarin +   
1,2,3-trimethylbenzene +  
1,2,4-trimethylbenzene +   
1,2,5,6,9,10-hexabromocyclododecane 
1,2-dibutyryl-sn-glycero-3-phospho-(1'D-myo-inositol) 
1,2-dibutyryl-sn-glycero-3-phospho-(1'D-myo-inositol-5'-phosphate) 
1,3-dinitrobenzene  
1-bromopropane  
1-butyryl-2-oleoyl-sn-glycerol 
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine +   
1-palmitoyl-2-butanoyl-sn-glycero-3-phosphocholine 
2,2,4-trihydroxybutanoic acid 
2,3,4-trihydroxybutanoic acid +   
2,3-dihydroxy-3-methylbutanoic acid +  
2,3-dihydroxybutanoic acid +  
2,4-diaminobutyric acid +  
2,4-dihydroxybutanoic acid 
2,5-hexanedione  
2-(hydroxymethyl)-4-oxobutanoic acid 
2-acetyllactic acid +  
2-amino-2-hydroxybutanoic acid 
2-amino-2-methylbutanoic acid 
2-amino-3-oxobutanoic acid +  
2-dehydro-3-deoxy-D-arabinonic acid 
2-hydroxybutyric acid +  
2-methylacetoacetic acid +  
2-oxobutanoic acid  
2-phenylbutyric acid 
3,4-dihydroxybutyric acid 
3,4-dihydroxymandelaldehyde 
3,4-methylenedioxymethamphetamine  
3-(indol-3-yl)-2-oxobutyric acid +  
3-aminobutanoic acid +  
3-dehydroquinic acid 
3-dehydroshikimic acid 
3-hydroxy-2-methylbutanoic acid +  
3-hydroxybutyric acid +   
3-hydroxyisovaleric acid +   
3-methyl-2-oxobutanoic acid  
3-methylfentanyl 
3-nitropropanoic acid  
3alpha-hydroxy-5beta-pregnan-20-one  
4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid 
4-(2-amino-5-hydroxyphenyl)-2,4-dioxobutanoic acid 
4-(2-aminophenyl)-2,4-dioxobutanoic acid 
4-(2-thienyl)butyric acid 
4-(5-ethyl-2-thienyl)-4-oxobutyric acid 
4-(hydroxymethylphosphinyl)-2-oxobutyric acid 
4-(methylamino)butyric acid 
4-[3-(3-nitrophenyl)-1,2,4-oxadiazol-5-yl]butanoic acid 
4-[4-(2,5-dioxopyrrolidin-1-yl)phenylamino]-4-hydroxybutyric acid 
4-[4-(3,5-dioxohexyl)phenylcarbamoyl]butyric acid 
4-guanidinobutanoic acid 
4-hydroxy-2-oxohexanoic acid +  
4-hydroxy-2-oxopentanoic acid +  
4-hydroxybutyric acid +   
A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.
4-hydroxylauric acid +  
4-methylthio-2-oxobutanoic acid +   
4-oxo-4-(2-thienyl)butyric acid 
4-oxo-4-phenylbutyric acid 
4-phenylbutyric acid  
5-chloro-4-hydroxy-2-oxopentanoic acid 
A-230 nerve agent 
A-232 nerve agent 
A-234 nerve agent 
aceprometazine +  
acetoacetic acid +   
acromelic acid A 
acrylamide  
adinazolam  
alpha-amino-gamma-cyanobutanoic acid 
alpha-aminobutyric acid +  
alprazolam  
ammonia +   
amphetamine +   
Aroclor 1254  
Batrachotoxin 
benzquinamide +  
bicuculline  
brexanolone 
bromisoval 
buspirone  
buspirone hydrochloride 
butalbital 
butane-1,4-diol +   
butyrate ester +   
butyryl group 
butyryl-CoA +   
butyrylglycine 
capuride 
carbon monoxide  
chloral hydrate  
chlordiazepoxide +   
chlorprothixene +   
chlorzoxazone  
cinolazepam 
D-2,4-diaminobutyric acid 
decabromodiphenyl ether  
decarbamoylsaxitoxin 
dexmedetomidine +   
dexmedetomidine hydrochloride 
dexormaplatin 
dextromethorphan +   
diazepam +   
dibutyrin +   
didesethylflurazepam 
diethyl phthalate  
dimethylbutyric acid +  
dinitrogen oxide  
diphenhydramine +   
diphenhydramine hydrochloride 
diphenhydramine salicylate 
discadenine 
domoic acid  
doxylamine  
edifenphos  
eszopiclone 
ethanol +   
ethchlorvynol 
ethinamate 
etomidate  
etorphine 
eucommiol 
fenadiazole 
flunitrazepam  
flurazepam +   
gamma-amino-beta-hydroxybutyric acid +  
gamma-amino-gamma-cyanobutanoic acid +  
gamma-aminobutyric acid +   
gamma-butyrolactone +  
heptafluorobutyric anhydride 
hexane +   
hexyl butyrate 
hydrogen peroxide +   
hydroxybutyric acid +   
hydroxyethylflurazepam 
Ibotenic acid  
indole-3-butyric acid +   
inhalation anaesthetic +   
intravenous anaesthetic +   
isooctanediol dibutyrate 
ketamine +   
L-2,4-diaminobutyric acid +  
L-2-amino-4-(hydroxymethylphosphinoyl)butanoic acid 
L-BMAA 
L-dopa +  
lactucin +  
lactucopicrin 
lead chromate  
lead(0) +   
lormetazepam 
mancozeb  
maneb +   
mercury(0)  
methamphetamine +   
methapyrilene +   
methapyrilene hydrochloride 
methaqualone 
methionine +   
methylbutyric acid +   
mianserin +   
midazolam +   
midazolam hydrochloride 
monobutyrin 
N-(butanoyl)ethanolamine 
N-butanoylserotonin 
N-butylbenzenesulfonamide  
N-butyryl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine 
N-hydroxy-PhIP  
N-methyl-4-phenylpyridinium  
neonicotinoid insectide +   
nicotine +   
nimetazepam  
nitrazepam +   
nordazepam  
O-butanoylcarnitine +   
O-hydroxybutyryl-L-carnitine +  
oltipraz  
omega-conotoxin GVIA  
ormaplatin 
oxidopamine  
pacatal 
paraldehyde  
perfluorobutyric acid  
periciazine  
phencyclidine  
phenobarbital +   
potassium cyanide  
promethazine  
promethazine hydrochloride 
propiomazine +  
propofol +   
rac-gabaculine 
remifentanil +   
remifentanil hydrochloride 
rolicyclidine 
S-butyryl-4'-phosphopantetheine 
sarin  
saxitoxin +   
secobarbital  
secobarbital sodium 
terpinolene +   
tetrodotoxin  
thalidomide +   
thallium(I) acetate  
thiamylal  
thiopental  
tinyatoxin 
toluene +   
trans-4-hydroxycyclohexanecarboxylic acid 
trazodone +   
trazodone hydrochloride 
triazolam  
tributyrin  
tricaine  
tricaine methanesulfonate 
trimethyltin  
TX-1875 
valerenic acid 
VR nerve agent 
VX nerve agent  
zaleplon  
zolpidem +   
zopiclone +   

Synonyms
Related Synonyms: 3-carboxypropoxy acid ;   4-Hydroxyalkanoic acid ;   4-Hydroxybutanoate ;   4-Hydroxybutanoic acid ;   4-Hydroxycarboxylic acid ;   4-hydroxy-butyric acid ;   Formula=C4H8O3 ;   GHB ;   Gamma Hydroxybutyric Acid ;   InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) ;   InChIKey=SJZRECIVHVDYJC-UHFFFAOYSA-N ;   SMILES=OCCCC(O)=O ;   Xyrem ;   oxy-n-butyric acid
Alternate IDs: CHEBI:1860 ;   CHEBI:20402 ;   CHEBI:386065
Xrefs: Beilstein:1720582 "Beilstein" ;   CAS:591-81-1 "ChemIDplus" ;   CAS:591-81-1 "DrugBank" ;   CAS:591-81-1 "KEGG COMPOUND" ;   CAS:591-81-1 "NIST Chemistry WebBook" ;   DrugBank:DB01440 ;   KEGG:C00989 ;   KEGG:C01991 ;   LIPID_MAPS_instance:LMFA01050006 "LIPID MAPS"
Xref Mesh: MESH:C111420
Xrefs: PMID:15927467 "ChEMBL" ;   PMID:3361576 "ChEMBL" ;   Reaxys:1720582 "Reaxys" ;   Wikipedia:Oxybate
Cyclic Relationships: is_conjugate_base_of CHEBI:16724

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.