(S)-3-hydroxybutanoate

362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API

144 compounds within 3 steps: 2 in 1, 16 in 2, 126 in 3

Three steps

N-(acetyl)-sphing-4-enineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetate and acetoacetate (cytosol to extracellular)
3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A6 and 3 moremitochondrial matrix, extracellular space, cytosol
all-trans-13,14-dihydroretinolReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
Catalysed by ADHFE1, D2HGDH, RETSATmitochondrial matrix
3,3',5-triiodo-L-thyronineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. 3,3',5-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2
Catalysed by ADHFE1, D2HGDH, DIO1, DIO2mitochondrial matrix
3,3',5'-triiodo-L-thyronineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. 3,3',5'-triiodo-L-thyronine + iodide + A + H(+) = L-thyroxine + AH2
Catalysed by ADHFE1, D2HGDH, DIO1, DIO3mitochondrial matrix
a 3-acylpyruvateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H(+)
Catalysed by ADHFE1, FAHD1mitochondrial matrix, cytosol
succinyl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA
3. 3-hydroxy-3-methylglutarate + succinyl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + succinate
Catalysed by ADHFE1, HMGCL, HMGCLL1, SUGCTmitochondrial matrix
(3S)-3-hydroxybutanoyl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate
3. (3S)-3-hydroxybutanoyl-CoA + NAD(+) = acetoacetyl-CoA + NADH + H(+)
Catalysed by ADHFE1, AACS, HADH, HSD17B10mitochondrial matrix
butanoyl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and butyrate (cytosol to extracellular)
3. Butanoate:CoA ligase (AMP-forming)
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A7 and 8 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes
glutaryl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA
3. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate
Catalysed by ADHFE1, HMGCL, HMGCLL1, SUGCTmitochondrial matrix
prostaglandin H2Reach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS1, PTGS2mitochondrial matrixOne of 2 routes
(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + AH2 = (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, TBXAS1, PTGS2 and 1 moremitochondrial matrix
N-acetyl-D-glucosamine 6-phosphateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetate and acetoacetate (cytosol to extracellular)
3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A6 and 3 moremitochondrial matrix, extracellular space, cytosol
2-oxo-3-sulfanylpropanoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. 2-oxo-3-sulfanylpropanoate + [thioredoxin]-dithiol = [thioredoxin]-disulfide + hydrogen sulfide + pyruvate + H(+)
Catalysed by ADHFE1, MPSTmitochondrial matrix, cytosol
2-methyl-3-oxopropanoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine
Catalysed by ADHFE1, AGXT2mitochondrial matrix, cytosol
succinate semialdehydeReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. 4-hydroxybutanoate + 2-oxoglutarate = (R)-2-hydroxyglutarate + succinate semialdehyde
3. 4-hydroxybutanoate + 2-oxoglutarate = (R)-2-hydroxyglutarate + succinate semialdehyde
Catalysed by ADHFE1mitochondrial matrixOne of 2 routes
L-methionineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
Catalysed by ADHFE1, TYW1B, TYW1mitochondrial matrix, cytosolOne of 5 routes
L-alanineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
Catalysed by ADHFE1, AGXT2mitochondrial matrix, cytosolOne of 20 routes
N-acetylputrescineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetate and acetoacetate (cytosol to extracellular)
3. N-acetylputrescine + H2O = putrescine + acetate
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A6 and 3 moremitochondrial matrix, extracellular space, cytosol
N(8)-acetylspermidineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetate and acetoacetate (cytosol to extracellular)
3. N(8)-acetylspermidine + H2O = spermidine + acetate
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A6 and 3 moremitochondrial matrix, extracellular space, cytosol
(3S)-citramalyl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA
Catalysed by ADHFE1, CLYBLmitochondrial matrix, cytosol
an N-acetyl-L-cysteine-S-conjugateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetate and acetoacetate (cytosol to extracellular)
3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate
Catalysed by ADHFE1, SLC16A4, SLC16A5, SLC16A6 and 3 moremitochondrial matrix, extracellular space, cytosol
5-amino-2-oxopentanoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine
Catalysed by ADHFE1, AGXT2mitochondrial matrix, cytosol
(4R)-4-hydroxy-2-oxoglutarateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate
Catalysed by ADHFE1, HOGA1mitochondrial matrix, cytosol
a 2,3-saturated acyl-CoAReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2
Catalysed by ADHFE1, D2HGDH, ACAD10mitochondrial matrix
(4S)-4-hydroxy-2-oxoglutarateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate
Catalysed by ADHFE1, HOGA1mitochondrial matrix, cytosol
(9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9S)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS1, PTGS2mitochondrial matrix
(9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9R)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS1, PTGS2mitochondrial matrix
(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
thio-Mo-molybdopterinReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
Catalysed by ADHFE1, D2HGDH, MOCOSmitochondrial matrix
O-3-oxobutanoyl-(R)-carnitineReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate
3. acetoacetyl-CoA + (R)-carnitine = O-3-oxobutanoyl-(R)-carnitine + CoA
Catalysed by ADHFE1, AACS, CRATmitochondrial matrix
2-glyceryl-prostaglandin H2Reach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
prostaglandin H1Reach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS2mitochondrial matrix
(13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. (R)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2
3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13S)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O
Catalysed by ADHFE1, D2HGDH, PTGS1, PTGS2mitochondrial matrix
2-(1-hydroxyethyl)thiamine diphosphateReach from here →
1. AKG[m] + (S)-3-hydroxybutanoate[m] = acetoacetate[m] + (R)-2-hydroxyglutarate[m]
2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)
Catalysed by ADHFE1, PDHA1, PDHB, PDHA2mitochondrial matrix, cytosol