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Information on EC 1.1.1.30 - 3-hydroxybutyrate dehydrogenase
for references in articles please use BRENDA:EC1.1.1.30
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.30 3-hydroxybutyrate dehydrogenase
IUBMB Comments
Also oxidizes other 3-hydroxymonocarboxylic acids.
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
- 1.1.1.30
- ketone
- succinate
- acetoacetate
-
lipid-requiring
- lecithin
-
coa-transferase
- acetoacetyl-coa
- alpha-glycerophosphate
-
thiolase
-
3-oxoacid
-
submitochondrial
-
ketogenesis
-
enzyme-phospholipid
- analysis
- diagnostics
- synthesis
showSynonyms
beta-hydroxybutyrate dehydrogenase, 3-hydroxybutyrate dehydrogenase, d-beta-hydroxybutyrate dehydrogenase, d-3-hydroxybutyrate dehydrogenase, beta-hydroxybutyric dehydrogenase, dhrs6, beta-hydroxybutyric acid dehydrogenase, 3-hbdh, 3-hydroxybutyrate dehydrogenase-2, 3hbdh, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-D-hydroxybutyrate dehydrogenase
-
-
-
-
3-HBDH
-
-
-
-
3-hydroxybutyrate dehydrogenase
-
-
-
-
3HBDH
BDH
BDH1
BDH2
BDH3
BdhA
beta-hydroxybutyrate dehydrogenase
beta-hydroxybutyric acid dehydrogenase
-
-
-
-
beta-hydroxybutyric dehydrogenase
-
-
-
-
D-(-)-3-hydroxybutyrate dehydrogenase
D-3-hydroxybutyrate dehydrogenase
D-beta-hydroxybutyrate dehydrogenase
HBD
HBDH
hydroxybutyrate oxidoreductase
-
-
-
-
NAD-beta-hydroxybutyrate dehydrogenase
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-
-
-
Psyc_1428
additional information
BDH
-
-
-
-
beta-hydroxybutyrate dehydrogenase
-
-
-
-
D-(-)-3-hydroxybutyrate dehydrogenase
-
-
-
-
D-3-hydroxybutyrate dehydrogenase
-
-
-
-
D-beta-hydroxybutyrate dehydrogenase
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-
-
-
additional information
-
the enzyme belongs to the family of short-chain dehydrogenases/reductases
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+
-
-
-
-
(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+
ordered Bi Bi mechanism, NAD+ first substrate, NADH last product to leave
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-
-
(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+
enzyme is completely dependent on the presence of phospholipid for activity
-
(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+
the enzyme shows a dynamical reaction mechanism. In the catalytic site, a water molecule is trapped by the catalytic Tyr155 and Ser142 residues in the vicinity of the bound NAD+ and acetate, substrate binding structure, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
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-
-
-
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SYSTEMATIC NAME
IUBMB Comments
(R)-3-hydroxybutanoate:NAD+ oxidoreductase
Also oxidizes other 3-hydroxymonocarboxylic acids.
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CAS REGISTRY NUMBER
COMMENTARY
9028-38-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-2-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: isoenzyme from heavy mitochondria and isoenzyme from light mitochondria show no significant difference in activity
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(R)-3-hydroxybutanoate + 3-acetylpyridine adenine dinucleotide
acetoacetate + 3-acetylpyridine adenine dinucleotideH2
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Substrates: -
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r
(R)-3-hydroxybutanoate + NADP+
acetoacetate + NADPH
Substrates: activity with NADP+ is 2% of the activity with NAD+
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?
2-hydroxypropansulfonate + NAD+
acetonylsulfonate + NADH
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Substrates: -
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r
2-methyl-3-hydroxybutyrate + NAD+
2-methylacetoacetate + NADH
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Substrates: -
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r
4-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: isoenzyme from heavy mitochondria shows 40% lower activity than enzyme fromlight mitochondria
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?
acetoacetate + NADH + H+
(R)-3-hydroxybutanoate + NAD+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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286513, 286514, 286516, 286517, 286521, 286522, 286525, 286527, 286528, 286530, 286535, 286538, 286540, 286542, 286543
Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: model of the binding mode of the substrate D-3-hydroxybutyrate, Gln193 is the only residue of the substrate-binding loop that interacts directly with the substrate, NAD+ binding increases the flexibility of the substrate-binding loop and shifts the equilibrium between the open and closed forms towards the closed form, overview
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NADH + H+
acetoacetate + NAD+
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Substrates: -
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r
(R)-3-hydroxybutanoate + NADH + H+
acetoacetate + NAD+
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Substrates: the enzyme is involved in poly(3-hydroxybutyrate) biosynthesis together with acetoacetyl-CoA thiolase and PHB synthase, pathway overview, intracellular concentrations of key metabolites, i.e. CoA, acetyl-CoA, 3HB-CoA, NAD+/NADH, determine whether a cell accumulates or degrades PHB
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r
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: strain SA1 can degrade poly((R)-3-hydroxybutyrate), i.e. PHB
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r
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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r
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
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Substrates: -
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(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
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Substrates: during hibernation, the enzyme is responsible for bioconvertion of high amounts of ketone bodies, i.e. acetoacetate and (R)-3-hydroxybutyrate, in the liver for usage as energetic fuel
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r
3-hydroxyvalerate + NAD+
3-oxovalerate + NADH + H+
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Substrates: -
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?
3-hydroxyvalerate + NAD+
3-oxovalerate + NADH + H+
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Substrates: -
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?
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: the reversible reactions occur by shuttle movements of a hydrogen negative ion from the C3 atom of the substrate to the C4 atom of NAD+ and from the C4 atom of NADH to the C3 atom of the product. The reaction may be further coupled to the withdrawal of a proton from the hydroxyl group of the substrate by the ionized Tyr155 residue
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH1 is needed to regulate the cytoplasmic redox state as well as to utilize 3-hydroxybutyrate
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH2 is needed to regulate the cytoplasmic redox state as well as to utilize 3-hydroxybutyrate
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH3 is specialized to utilize 3-hydroxybutyrate
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH3 is specialized to utilize 3-hydroxybutyrate
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH2 is needed to regulate the cytoplasmic redox state as well as to utilize 3-hydroxybutyrate
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r
D-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: BDH1 is needed to regulate the cytoplasmic redox state as well as to utilize 3-hydroxybutyrate
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r
levulinic acid + NADH + H+
4-hydroxyvaleric acid + NAD+
Substrates: only the recombinant wild type enzyme with N-terminal His-tag shows activity with levulinic acid
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?
levulinic acid + NADH + H+
4-hydroxyvaleric acid + NAD+
Substrates: the wild type enzyme shows low activity with levulinic acid, while it's a good substrate for mutant enzyme H144L/W187F
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?
poly-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
poly-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
additional information
?
-
-
Substrates: no activity of the wild-type enzyme with levulinic acid, enzyme mutant H144L/W187F is active with levulinic acid producing 4-hydroxyvaleric acid
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?
additional information
?
-
-
Substrates: enzyme activity is differently regulated in liver and brain at euthermic, prehibernating,and hibernating state
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?
additional information
?
-
-
Substrates: a ketone body converting enzyme in mitochondria in liver jerboa, enzyme expression, activity and metabolism at different physiological states, overview
Products: -
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-3-hydroxybutanoate + NADH + H+
acetoacetate + NAD+
-
Substrates: the enzyme is involved in poly(3-hydroxybutyrate) biosynthesis together with acetoacetyl-CoA thiolase and PHB synthase, pathway overview, intracellular concentrations of key metabolites, i.e. CoA, acetyl-CoA, 3HB-CoA, NAD+/NADH, determine whether a cell accumulates or degrades PHB
Products: -
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r
acetoacetate + NADH + H+
(R)-3-hydroxybutanoate + NAD+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
Products: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
Products: -
Products: -
r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
286513, 286514, 286516, 286517, 286521, 286522, 286525, 286527, 286528, 286530, 286535, 286538, 286540, 286542, 286543
Substrates: -
Products: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
-
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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r
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
Products: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
Substrates: -
Products: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
-
Substrates: -
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?
(R)-3-hydroxybutanoate + NAD+
acetoacetate + NADH + H+
-
Substrates: -
Products: -
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?
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
Substrates: strain SA1 can degrade poly((R)-3-hydroxybutyrate), i.e. PHB
Products: -
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r
(R)-3-hydroxybutyrate + NAD+
acetoacetate + NADH + H+
-
Substrates: during hibernation, the enzyme is responsible for bioconvertion of high amounts of ketone bodies, i.e. acetoacetate and (R)-3-hydroxybutyrate, in the liver for usage as energetic fuel
Products: -
Products: -
r
additional information
?
-
-
Substrates: enzyme activity is differently regulated in liver and brain at euthermic, prehibernating,and hibernating state
Products: -
Products: -
?
additional information
?
-
-
Substrates: a ketone body converting enzyme in mitochondria in liver jerboa, enzyme expression, activity and metabolism at different physiological states, overview
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
-
-
286513, 286514, 286516, 286517, 286521, 286522, 286525, 286527, 286528, 286530, 286535, 286538, 286540, 286542, 286543
NAD+
NAD+ is bound in a large cleft in the domain. The diphosphate group of NAD+ is covered by the small additional domain, which is supported by two extended arms allowing domain movement
NAD+
the substrate-binding loop, residues 187-210, is partially disordered in several subunits, in both the presence and absence of NAD+, closed conformation in the complex structure with NAD+, interactions of Val185, Thr187 and Leu189 with the cosubstrate induced the conformational change from open to closed, NAD+ binding increases the flexibility of the substrate-binding loop and shifts the equilibrium between the open and closed forms towards the closed form
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Mg2+
Mn2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,4-Dichlorophenoxyacetic acid
-
inhibits the enzyme, in vivo treatment of the animals with 2,4-dichlorophenoxyacetic acid leads to strong decrease of triglycerides level and HDL cholesterol and an increase in GOT level and LDL cholesterol, and necrosis of seminiferous tubules cells in testis, hyperplasia of hepatocytes in liver and presence of multinucleated giant cells in brain, overview
3-hydroxybutyrate
-
substrate inhibition at concentrations above 20 mM, 50% inhibition at 200 mM, cyanylated enzyme is 3fold more active at high substrate concentration
4-mercapto-3-nitrobenzoate
-
derivatization of enzyme sulfhydryl groups, less than 1% residual activity
ADP
-
2.85 mM, 0.025 mM NADH, 63% inhibition, competitive inhibitor vs. NADH and NAD+, pH 7-7.5, noncompetitive vs. acetoacetate
ADP-ribose
-
competitive inhibition vs. coenzyme, noncompetitive vs. substrate
AMP
-
2.85 mM, 0.025 mM NADH, 55% inhibition, competitive inhibitor vs. NADH and NAD+, pH 7-7.5
ATP
-
2.85 mM, 0.025 mM NADH, 79% inhibition, competitive inhibitor vs. NADH and NAD+, pH 7-7.5, noncompetitive vs. acetoacetate
D-lactate
-
5 mM, pH 8.5, 25°, 85% inhibition, uncompetitive vs. coenzyme, competitive vs. substrate
Methyl-2-methoxyphosphinylacetate
-
competitive inhibitor vs. acetoacetate
NAD+
-
substrate inhibition, high concentrations, noncompetitive vs. beta-hydroxybutyrate
pyruvate