Information on EC 1.14.14.18 - heme oxygenase (biliverdin-producing)

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.14.18
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RECOMMENDED NAME
GeneOntology No.
heme oxygenase (biliverdin-producing)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
protoheme + 3 [reduced NADPH-hemoprotein reductase] + 3 O2 = biliverdin + Fe2+ + CO + 3 [oxidized NADPH-hemoprotein reductase] + 3 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
heme degradation
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heme metabolism
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Porphyrin and chlorophyll metabolism
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SYSTEMATIC NAME
IUBMB Comments
protoheme,NADPH-hemoprotein reductase:oxygen oxidoreductase (alpha-methene-oxidizing, hydroxylating)
This mammalian enzyme participates in the degradation of heme. The terminal oxygen atoms that are incorporated into the carbonyl groups of pyrrole rings A and B of biliverdin are derived from two separate oxygen molecules [4]. The third oxygen molecule provides the oxygen atom that converts the alpha-carbon to CO. The enzyme requires NAD(P)H and EC 1.6.2.4, NADPH---hemoprotein reductase. cf. EC 1.14.15.20, heme oxygenase (biliverdin-producing, ferredoxin).
CAS REGISTRY NUMBER
COMMENTARY hide
9059-22-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
two types of isoforms: an inducible heme oxygenase-1, HO1, and a constitutive heme oxygenase-2/3, HO2/3
UniProt
Manually annotated by BRENDA team
gene chuZ
Q5HSH8
UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
guinea pig
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain O157:H7
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Manually annotated by BRENDA team
heme oxygenase-1 is identical to the major 32000 Da mammalian stress-protein inducible by heat shock, H2O2, ultraviolet-A radiation, NaAsO2, pro-inflammatory cytokines, bacterial endotoxins, growth factors, NO, and tumor promotors, heme oxygenase-1 confers protection against oxidative stress
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
C3H/HeN mice
UniProt
Manually annotated by BRENDA team
C57BL/6 mice
UniProt
Manually annotated by BRENDA team
gene hemO; two genes pigA encoding PigA homologues
UniProt
Manually annotated by BRENDA team
; PigA; gene pigA
UniProt
Manually annotated by BRENDA team
; PigA; gene pigA
UniProt
Manually annotated by BRENDA team
two genes pigA encoding PigA homologues
UniProt
Manually annotated by BRENDA team
two genes pigA encoding PigA homologues
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
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isoform HO-1 modulates the function of transcriptional factor Nuclear factor erythroid 2-related factor 2 (Nrf2). In oxidative stress, nuclear isoform HO-1 interacts with Nrf2 and stabilizes it from glycogen synthase kinase 3beta-mediated phosphorylation coupled with ubiquitin-proteasomal degradation, thereby prolonging its accumulation in the nucleus
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
15-phenylheme + electron donor + O2
10-phenylbiliverdin IXalpha + Fe2+ + CO + oxidized eletron donor + H2O
show the reaction diagram
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-
-
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5-phenylheme + electron donor + O2
biliverdin IXalpha + Fe2+ + CO + oxidized eletron donor + H2O + benzoic acid
show the reaction diagram
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-
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alpha-meso-formylmesoheme + NADPH
? + NADP+
show the reaction diagram
-
exclusively oxidized at a non-formyl substituted meso-carbon
-
?
alpha-meso-hydroxyhemin IX + reduced acceptor + O2
verdoheme IXalpha + CO + acceptor + H2O
show the reaction diagram
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-
-
-
?
beta-meso-hydroxyhemin IX + reduced acceptor + O2
verdoheme IXbeta + CO + acceptor + H2O
show the reaction diagram
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-
-
-
?
delta-meso-hydroxyhemin IX + reduced acceptor + O2
verdoheme IXdelta + CO + acceptor + H2O
show the reaction diagram
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-
-
-
?
gamma-CH-Fe(cor) + 3 AH2 + 3 O2
?
show the reaction diagram
gamma-meso-hydroxyhemin IX + reduced acceptor + O2
verdoheme IXgamma + CO + acceptor + H2O
show the reaction diagram
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-
-
-
?
heme + 2 NADH + 2 H+ + 2 O2
biliverdin + Fe2+ + CO + 2 NAD+ + H2O
show the reaction diagram
-
NADH-dependent heme degradation system may have a biological role in regulating the concentration of respiratory hemoproteins and the disposition of the aberrant forms of the mitochondrial hemoproteins
-
?
heme + 2 NADPH + 2 H+ + 2 O2
biliverdin + Fe2+ + CO + 2 NADP+ + H2O
show the reaction diagram
heme + 3 AH2 + 3 O2
biliverdin + Fe2+ + CO + 3 A + 3 H2O
show the reaction diagram
heme + 3 AH2 + 3 O2
biliverdin IXalpha + Fe2+ + CO + 3 A + 3 H2O
show the reaction diagram
heme + 3 reduced ascorbate + 3 O2
biliverdin + Fe2+ + CO + 3 oxidized ascorbate + 3 H2O
show the reaction diagram
heme + AH2 + O2
biliverdin + Fe2+ + CO + A + H2O
show the reaction diagram
heme + electron donor + O2
alpha-biliverdin + beta-biliverdin + delta-biliverdin + Fe2+ + CO + oxidized eletron donor + H2O
show the reaction diagram
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wild-type, mutant N19K, mutant F117Y, 30% beta- and 70% delta-isomer, N19K/F117Y double mutant, 55% alpha-, 10% beta-, 35% delta-isoform
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?
heme + electron donor + O2
biliverdin + Fe2+ + CO + oxidized electron donor + H2O
show the reaction diagram
heme + electron donor + O2
biliverdin + Fe2+ + CO + oxidized eletron donor + H2O
show the reaction diagram
heme + electron donor + O2
biliverdin IXalpha + Fe2+ + CO + oxidized eletron donor + H2O
show the reaction diagram
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prefers ferredoxin or ascorbate as electron donor
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-
?
heme + ferredoxin + O2
biliverdin IXalpha + Fe2+ + CO + A + H2O
show the reaction diagram
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HY1, HO3, and HO4
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-
?
heme + NADH + O2
biliverdin + Fe2+ + CO + NAD+ + H2O
show the reaction diagram
heme + NADPH + O2
biliverdin IXalpha + Fe2+ + CO + NADP+ + H2O
show the reaction diagram
heme + NADPH + O2
biliverdin IXdelta + biliverdin IXalpha + Fe2+ + CO + NADP+ + H2O
show the reaction diagram
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mutant R183E, yields about 20% of product biliverdin IXdelta
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?
hemin + reduced acceptor + O2
alpha-meso-hydroxyhemin IX + CO + acceptor + H2O
show the reaction diagram
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-
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-
?
methemoglobin + electron donor + O2
?
show the reaction diagram
protoheme + [reduced NADPH-hemoprotein reductase] + O2
biliverdin + Fe2+ + CO + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
verdoheme IXalpha + H2O
biliverdin IXalpha + Fe2+
show the reaction diagram
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additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
heme + 2 NADH + 2 H+ + 2 O2
biliverdin + Fe2+ + CO + 2 NAD+ + H2O
show the reaction diagram
-
NADH-dependent heme degradation system may have a biological role in regulating the concentration of respiratory hemoproteins and the disposition of the aberrant forms of the mitochondrial hemoproteins
-
?
heme + 2 NADPH + 2 H+ + 2 O2
biliverdin + Fe2+ + CO + 2 NADP+ + H2O
show the reaction diagram
heme + 3 AH2 + 3 O2
biliverdin + Fe2+ + CO + 3 A + 3 H2O
show the reaction diagram
heme + 3 AH2 + 3 O2
biliverdin IXalpha + Fe2+ + CO + 3 A + 3 H2O
show the reaction diagram
heme + AH2 + O2
biliverdin + Fe2+ + CO + A + H2O
show the reaction diagram
protoheme + [reduced NADPH-hemoprotein reductase] + O2
biliverdin + Fe2+ + CO + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
ferredoxin-NADP+-oxidoreductase
NADH
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NADPH is more effective than NADH
NADPH
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cd2+
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0.2 mM, induction of enzyme and 4.5fold enhancement of activity, biliverdin partly prevents
CoCl2
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activates
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
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IC50: 0.00006 mM
(+-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
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IC50: 0.0062 mM
(+-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
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IC50: 0.00014 mM
(+-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
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IC50: 0.0005 mM
(+-)-4-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
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IC50: 0.0014 mM
(+/-)-1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanol hydrochloride
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(+/-)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol hydrochloride
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(+/-)-4-(4-bromophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
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(+/-)-4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol hydrochloride
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(2-[2-(4-chlorophenyl)ethyl]-2-[1H-imidazol-1-yl)methyl]-1,3-dioxolane
;
(2E)-2-[4-(dimethylamino)benzylidene]hydrazinecarboximidamide
(2E)-2-[[4-(dimethylamino)phenyl]methylidene]hydrazinecarboximidamide
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-(methoxymethyl)-1,3-dioxolane hydrochloride monohydrate
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potent but non-selective inhibitor of HO-2
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-(phenoxymethyl)-1,3-dioxolane hydrochloride
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potent but non-selective inhibitor of HO-2
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-methyl-1,3-dioxolane
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane dihydrochloride dihydrate
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(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(4-iodophenoxy)methyl]-1,3-dioxolane hydrochloride
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(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(4-methoxyphenoxy)methyl]-1,3-dioxolane hydrochloride
-
moderately high potency and selectivity toward HO-1
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-4-(hydroxymethyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
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-
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-4-[(4-cyanophenoxy)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
potent but non-selective inhibitor of HO-2
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-4-[(4-fluorophenoxy)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
potent but non-selective inhibitor of HO-2
(2R,4R)-2-[2-(4-chlorophenyl)ethyl]-4-[(4-hydroxyphenoxy)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
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(2R,4R)-4-(aminomethyl)-2-[(1H-imidazol-1-yl)methyl]-2-[(2-phenyl)ethyl]-1,3-dioxolane dihydrochloride
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(2R,4R)-4-(azidomethyl)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane
-
moderately high potency and selectivity toward HO-1
(2R,4R)-4-[((4-adamantan-1-yl)phenoxy)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
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(2R,4R)-4-[(4-aminophenoxy)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane dihydrochloride
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(2R,4R)-4-[(4-bromophenoxy)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
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(2R,4R)-4-[(biphenyl-4-yloxy)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
moderately high potency and selectivity toward HO-1
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)-methyl]-4-methyl-1,3-dioxolane
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IC50: 0.0026 mM
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((5-trifluoromethyl)pyridin-2-ylsulfanyl)methyl]-1,3-dioxolane hydrochloride
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(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((5-trifluoromethylpyridin-2-yl)thio)methyl]-1,3-dioxolane
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(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(4-methoxyphenylsulfanyl)methyl]-1,3-dioxolane hydrochloride
-
potent but non-selective inhibitor of HO-2
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(4-nitrophenylsulfanyl)methyl]-1,3-dioxolane hydrochloride
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(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(methylthio)methyl]-1,3-dioxolane hydrochloride
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-
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(naphthalen-2-ylsulfanyl)methyl]-1,3-dioxolane hydrochloride
-
moderately high potency and selectivity toward HO-1
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(phenylsulfanyl)methyl]-1,3-dioxolane hydrochloride
-
moderately high potency and selectivity toward HO-1
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(phenylsulphanyl)methyl]-1,3-dioxolane
-
-
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(pyridin-4-ylsulfanyl)methyl]-1,3-dioxolane dihydrochloride
-
-
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-4-(fluoromethyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
potent but non-selective inhibitor of HO-2
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-4-[(4-chlorophenylsulfanyl)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
-
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-4-[(4-fluorophenylsulfanyl)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
-
(2R,4S)-2-[2-(4-chlorophenyl)ethyl]-4-[(cyclohexylsulfanyl)methyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
moderately high potency and selectivity toward HO-1
(2R,4S)-4-(chloromethyl)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride monohydrate
-
moderately high potency and selectivity toward HO-1
(2R,4S)-4-[(2-bromophenylsulfanyl)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
-
(2R,4S)-4-[(3-bromophenylsulfanyl)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
-
(2R,4S)-4-[(4-bromophenylsulfanyl)methyl]-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolane hydrochloride
-
potent but non-selective inhibitor of HO-2
(2S, 4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[((4-aminophenyl)thio)methyl]-1,3-dioxolane
(2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)-methyl]-4-methyl-1,3-dioxolane
-
IC50: 0.02 mM
(2S,4S)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-methyl-1,3-dioxolane
-
IC50: 0.012 mM
(2Z)-4-[(4-anilinophenyl)amino]-4-oxobut-2-enoic acid
(2Z)-N'-[(1Z)-pyridin-3-ylmethylene]-2-(pyridin-3-ylmethylene)hydrazinecarboximidohydrazide
(2Z)-N'-[(1Z)-pyridin-3-ylmethylidene]-2-(pyridin-3-ylmethylidene)hydrazinecarboximidohydrazide
(R,S)-1-(1H-imidazol-1-yl)-4-phenyl-2-butanol
-
-
(R,S)-1-(4,5-diphenyl-1H-imidazol-1-yl)-4-phenyl-2-butanol
-
-
(R,S)-4-phenyl-1-(1H-1,2,3-triazol-1-yl)-2-butanol
-
-
(R,S)-4-phenyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol
-
-
(R,S)-4-phenyl-1-(1H-tetrazol-1-yl)-2-butanol
-
-
(R,S)-4-phenyl-1-(2H-tetrazol-2-yl)-2-butanol
-
-
(R,S)-4-phenyl-1-(4-phenyl-1H-imidazol-1-yl)-2-butanol
-
-
1,10-phenanthroline
1-((2-(2-(4-bromophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
-
; IC50: 0.0019 mM
1-((2-(2-(4-chlorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
-
; IC50: 0.0043 mM
1-((2-(2-(4-fluorophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
-
; IC50: 0.0038 mM
1-((2-(2-(4-iodophenyl)ethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
-
; IC50: 0.0037 mM
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-1,2,3-triazole
-
-
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole
-
-
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-imidazole hydrochloride
-
; IC50: 0.0007 mM
1-((2-(2-phenylethyl)-1,3-dioxolan-2-yl)methyl)-1H-tetrazole
-
-
1-((2-phenylethyl)-1,3-dioxolan-2-yl)methyl-1H-imidazole
-
-
1-((2-phenylethyl-1,3-dioxolan-2-yl)methyl)-4,5-diphenyl-1H-imidazole
-
-
1-((2-phenylethyl-1,3-dioxolan-2-yl)methyl)-4-phenyl-1H-imidazole
-
-
1-(1H-benzimidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(1H-benzotriazol-1-yl)-4-phenyl-2-butanone
-
-
1-(1H-imidazol-1-yl)-4,4-diphenyl-2-butanone
-
1-(1H-imidazol-1-yl)-4-(4-iodophenyl)-2-butanone hydrochloride
-
; IC50: 0.00011 mM
1-(1H-imidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride
-
; IC50: 0.004 mM
1-(2,3-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2,4-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2,4-dinitrophenyl)methanamine
1-(2,5-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2,6-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-bromobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-cyanobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-methyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(2-methylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-methylsulfonyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(2-methylthio-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(2-nitro-1H-imidazol-1-yl)-4-phenyl-2-butanone
-
-
1-(2-nitrobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-phenoxyethyl)-1H-imidazole
-
-
1-(2-phenoxyethyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-phenylethyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2-phenylmethyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(2H-benzotriazol-2-yl)-4-phenyl-2-butanone
-
-
1-(3,4-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
-
1-(3,5-dichlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
-
-
1-(3-bromobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3-cyanobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3-methylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
-
1-(3-methylsulfonyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(3-methylthio-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(3-nitro-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(3-nitrobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(3-phenyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(4,5-dichloro-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(4,5-dicyano-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(4,5-diphenyl-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(4-benzyloxybenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-bromo-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(4-bromobenzyl)-2-(1H-imidazol-1-yl)methyl-1H-benzimidazole
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1-(4-bromobenzyl)-2-(N-morpholinyl)methyl-1H-benzimidazole
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1-(4-bromobenzyl)-2-(norborn-2-yl)methyl-1H-benzimidazole hydrochloride
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1-(4-bromobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-bromobenzyl)-2-cyclopentylmethyl-1H-benzimidazole
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1-(4-bromophenyl)-2-(1H-imidazol-1-yl)ethanone
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1-(4-bromophenyl)-2-[2-(1-methylethyl)-1H-imidazol-1-yl]ethanone
1-(4-chlorobenzyl)-2-(1H-imidazol-1-yl)methyl-1H-benzimidazole
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1-(4-chlorobenzyl)-2-(2-norbornylmethyl)-1H-benzimidazole hydrochloride
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1-(4-chlorobenzyl)-2-(N-morpholinyl)methyl-1H-benzimidazole
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1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-chlorobenzyl)-2-cyclopentylmethyl-1H-benzimidazole
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1-(4-cyanobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-fluorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-iodobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-isopropylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-methoxybenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-methylbenzyl)-2-(N-morpholinyl)methyl-1H-benzimidazole hydrochloride
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1-(4-methylbenzyl)-2-(norborn-2-yl)methyl-1H-benzimidazole hydrochloride
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1-(4-methylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-nitro-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(4-nitrobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-thiomethylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(4-trifluoromethylbenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(5-bromo-1H-imidazol-1-yl)-4-phenyl-2-butanone
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1-(5-methylsulfonyl-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(5-methylsulfonyl-1H-tetrazol-1-yl)-4-phenyl-2-butanone
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1-(5-methylsulfonyl-2H-tetrazol-2-yl)-4-phenyl-2-butanone
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1-(5-methylthio-1H-1,2,4-triazol-1-yl)-4-phenyl-2-butanone
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1-(5-methylthio-1H-tetrazol-1-yl)-4-phenyl-2-butanone
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1-(5-methylthio-2H-tetrazol-2-yl)-4-phenyl-2-butanone
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1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone
1-(cyclohexylmethyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-(n-heptyl)-2-(norborn-2-yl)methyl-1H-benzimidazole hydrochloride
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1-(n-hexyl)-2-(norborn-2-yl)methyl-1H-benzimidazole hydrochloride
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1-(naphthalen-2-ylmethyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-benzhydryl-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole
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1-benzyl-2-(1H-imidazol-1-yl)methyl-1H-benzimidazole
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1-benzyl-2-(N-morpholinyl)methyl-1H-benzimidazole hydrochloride
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1-benzyl-2-(norborn-2-yl)methyl-1H-benzimidazole hydrochloride
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1-benzyl-2-cyclohexylmethyl-1H-benzimidazole hydrochloride
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1-bromo-4-phenyl-2-butanone
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1-bromobenzyl-2-cyclohexylmethyl-1H-benzimidazole hydrochloride
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