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Information on EC 5.5.1.6 - chalcone isomerase
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EC Tree
5.5.1.6 chalcone isomeraseSpecify your search results
Word Map
- 5.5.1.6
- flavonoid
- anthocyanins
- dihydroflavonol
-
ammonia-lyase
- naringenin
-
phenylpropanoids
- anthocyanidin
-
4-reductase
- cinnamate
- isoflavone
- flavone
-
4-hydroxylase
-
isoflavonoids
-
3\'-hydroxylase
- 3-o-glucosyltransferase
-
r2r3-myb
-
4-coumarate:coa
-
leucoanthocyanidin
- 4-coumarate
-
3',5'-hydroxylase
- agriculture
- petroselinum
- 2s-naringenin
-
2s-flavanones
- analysis
- lindemuthianum
-
4.3.1.5
- synthesis
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
chalcone isomerase, chalcone-flavanone isomerase, chi-1, chil1, mpchi, chil2, slchi1, chi1a, chalcone isomerase-like protein, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Chalcone isomerase
chalcone isomerase-like protein
Chalcone-flavanone isomerase
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-
-
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CHI
Chi1
CHI1A
CHI1B2
CHI2
Isomerase, chalcone
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-
-
-
taxifolin-isomerizing enzyme
TRANSPARENT TESTA 5 protein
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-
-
-
Chalcone isomerase
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-
-
-
CHI
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
A chalcone = a flavanone
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-
-
-
A chalcone = a flavanone
rate limiting step is an intramolecular Michael addition of a 2-oxyanion to the alpha,beta-double bond. Computational study shows that the active site conformation with larger catalytic power presents a positively charged lysine resiude much closer to the substrate than the second active site. Charge is transferred from the 2-oxyanion to the beta-carbon atom
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
elimination/addition
-
-
intramolecular
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
flavanone lyase (decyclizing)
-
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CAS REGISTRY NUMBER
COMMENTARY
9073-57-8
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E)-3-(2-fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(2-fluorophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
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based on substrate (2E)-3-(2-fluorophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
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-
?
(2E)-3-(2-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
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based on substrate (2E)-3-(2-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
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-
?
(2E)-3-(3-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-5,7-dihydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
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based on substrate (2E)-3-(3-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(4-aminophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(4-aminophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
-
based on substrate (2E)-3-(4-aminophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
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-
?
(2E)-3-(4-fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(4-fluorophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
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based on substrate (2E)-3-(4-fluorophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
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based on substrate (2E)-3-(4-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
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-
?
2',4'-dihydroxy-4-methylchalcone
7-hydroxy-2-(4-methyl-phenyl)-chroman-4-one
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-
-
?
4,2',4',6'-tetrahydroxychalcone
5,7-dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
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-
-
?
4,2',4'-trihydroxychalcone
7-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
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-
-
?
4,2',5'-trihydroxychalcone
6-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
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-
-
?
4,2'-dihydroxychalcone
2-(4-hydroxy-phenyl)-chroman-4-one
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-
-
?
(+)-dihydrokaempferol
maesopsin
60% activity compared to (+)-taxifolin
-
-
?
(+)-dihydrokaempferol
maesopsin
Eubacterium ramulus DSM 16296
60% activity compared to (+)-taxifolin
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-
?
2',4'-dihydroxychalcone
7-hydroxy-2-phenyl-chroman-4-one
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-
-
?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
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i.e. naringenin chalcone
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?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
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-
i.e. naringenin
?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
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-
-
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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no activity
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-
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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highly stereoselective product formation
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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r, at pH 7.6
the product is liquiritigenin
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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-
the product is liquiritigenin
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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i.e. isoliquiritigenin
the product is liquiritigenin
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
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no activity
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-
?
6'-deoxychalcone
?
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
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?
6'-hydroxychalcone
?
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two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
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?
6'-hydroxychalcone
?
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two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
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?
a chalcone
a flavanone
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-
-
?
butein
(S)-eriodictyol
less than 1% activity compared to (+)-taxifolin
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-
?
butein
(S)-eriodictyol
Eubacterium ramulus DSM 16296
less than 1% activity compared to (+)-taxifolin
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-
?
isoliquiritigenin
liquiritigenin
low activity compared to naringenin chalcone
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-
?
naringenin chalcone
(2S)-naringenin
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naringenin chalcone (6'-hydroxychalcone) is the only substrate
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-
?
additional information
?
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presence of a premature stop codon in the gold CHI gene results in an inactive chalcone isomerase. Inactivation of chalcone isomerase results in a block in the flavonoid biosynthesis pathway and the accumulation of chalcone derivatives, including a yellow pigment which might be responsible for the unusual gold color in onion
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?
additional information
?
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the enzyme plays an important role in flavonoid metabolism
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?
additional information
?
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no activity with (-)-taxifolin, (-)-dihydrokaempferol, naringenin, or eriodictyol
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?
additional information
?
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no activity with (-)-taxifolin, (-)-dihydrokaempferol, naringenin, or eriodictyol
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?
additional information
?
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Eubacterium ramulus DSM 16296
no activity with (-)-taxifolin, (-)-dihydrokaempferol, naringenin, or eriodictyol
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-
?
additional information
?
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the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
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involved in biosynthesis of 5-hydroxyflavonoids, 5-deoxyflavonoids and retrochalcone
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-
?
additional information
?
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-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
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the enzyme is an essential compound in the biosynthesis of anthocyanin pigments, inducers of Rhizobium nodulation genes, and antimicrobial phytoalexins
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?
additional information
?
-
the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
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?
additional information
?
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the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
-
-
?
additional information
?
-
CHI is involved in the anthocyanin biosynthetic pathway
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-
?
additional information
?
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-
CHI is involved in the anthocyanin biosynthetic pathway
-
-
?
additional information
?
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-
light-induced increase in activity, enzyme of phenylpropanoid metabolism
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-
?
additional information
?
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-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
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-
the enzyme catalyzes a step common to the synthesis of flavonoid pigments and isoflavonoid phytoalexins
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
elicitor, heat-released from cell walls of the phytopathogenic fungus Colletotrichum lindemuthianum, induces synthesis of both active and inactive chalcone isomerase
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-
?
additional information
?
-
key role of the enzyme in total flavonoid and apigenin synthesis
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-
?
additional information
?
-
-
key role of the enzyme in total flavonoid and apigenin synthesis
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
6'-deoxychalcone
?
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
6'-hydroxychalcone
?
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
a chalcone
a flavanone
-
-
-
?
additional information
?
-
-
presence of a premature stop codon in the gold CHI gene results in an inactive chalcone isomerase. Inactivation of chalcone isomerase results in a block in the flavonoid biosynthesis pathway and the accumulation of chalcone derivatives, including a yellow pigment which might be responsible for the unusual gold color in onion
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
involved in biosynthesis of 5-hydroxyflavonoids, 5-deoxyflavonoids and retrochalcone
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
the enzyme is an essential compound in the biosynthesis of anthocyanin pigments, inducers of Rhizobium nodulation genes, and antimicrobial phytoalexins
-
?
additional information
?
-
the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
-
-
?
additional information
?
-
-
the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
-
-
?
additional information
?
-
CHI is involved in the anthocyanin biosynthetic pathway
-
-
?
additional information
?
-
-
CHI is involved in the anthocyanin biosynthetic pathway
-
-
?
additional information
?
-
-
light-induced increase in activity, enzyme of phenylpropanoid metabolism
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
the enzyme catalyzes a step common to the synthesis of flavonoid pigments and isoflavonoid phytoalexins
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
additional information
?
-
-
elicitor, heat-released from cell walls of the phytopathogenic fungus Colletotrichum lindemuthianum, induces synthesis of both active and inactive chalcone isomerase
-
-
?
additional information
?
-
key role of the enzyme in total flavonoid and apigenin synthesis
-
-
?
additional information
?
-
-
key role of the enzyme in total flavonoid and apigenin synthesis
-
-
?
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.