DB code: D00453

CATH domain 1.10.890.20 : 10k-s Protein, Hypothetical Protein A; Chain A
3.50.70.10 : Chalcone isomerase Catalytic domain
E.C. 5.5.1.6
CSA 1eyp
M-CSA 1eyp
MACiE M0196

CATH domain Related DB codes (homologues)

Uniprot Enzyme Name
UniprotKB Protein name Synonyms Pfam
P28012 Chalcone--flavonone isomerase 1
Chalcone isomerase 1
EC 5.5.1.6
PF02431 (Chalcone)
[Graphical View]

KEGG enzyme name
chalcone isomerase
chalcone-flavanone isomerase

UniprotKB: Accession Number Entry name Activity Subunit Subcellular location Cofactor
P28012 CFI1_MEDSA A chalcone = a flavanone.

KEGG Pathways
Map code Pathways E.C.
MAP00941 Flavonoid biosynthesis

Compound table
Substrates Products Intermediates
KEGG-id C06561 C09321 C08650 C00509 C00766 C09762
E.C.
Compound Isosalipurpol 2'-Hydroxychalcone Isoliquiritigenin Naringenin Flavanone Liquiritigenin
Type aromatic ring (only carbon atom),carbohydrate aromatic ring (only carbon atom),carbohydrate aromatic ring (only carbon atom),carbohydrate aromatic ring (only carbon atom),carbohydrate aromatic ring (only carbon atom),carbohydrate aromatic ring (only carbon atom),carbohydrate
ChEBI 15413
 15413
 		27916
 27916
 		310312
 310312
 		17846
 17846
 		5070
 5070
 		28777
 28777
PubChem 5280960
 5280960
 		638276
 638276
 		638278
 638278
 		439246
 439246
 		10251
 10251
 		114829
 114829
1eypA01 Unbound Unbound Unbound Unbound Unbound Unbound
1eypB01 Unbound Unbound Unbound Unbound Unbound Unbound
1eyqA01 Unbound Unbound Unbound Unbound Unbound Unbound
1eyqB01 Unbound Unbound Unbound Unbound Unbound Unbound
1fm7A01 Unbound Unbound Unbound Unbound Unbound Unbound
1fm7B01 Unbound Unbound Unbound Unbound Unbound Unbound
1fm8A01 Unbound Unbound Unbound Unbound Unbound Unbound
1fm8B01 Unbound Unbound Unbound Unbound Unbound Unbound
1jepA01 Unbound Unbound Unbound Unbound Unbound Unbound
1jepB01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx0A01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx0B01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1A01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1B01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1C01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1D01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1E01 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1F01 Unbound Unbound Unbound Unbound Unbound Unbound
1eypA02 Unbound Unbound Unbound Unbound Unbound Unbound
1eypB02 Unbound Unbound Unbound Unbound Unbound Unbound
1eyqA02 Unbound Unbound Unbound Bound:NAR Unbound Unbound
1eyqB02 Unbound Unbound Unbound Bound:NAR Unbound Unbound
1fm7A02 Unbound Unbound Unbound Unbound Unbound Bound:DFV
1fm7B02 Unbound Unbound Unbound Unbound Unbound Bound:DFV
1fm8A02 Unbound Unbound Unbound Unbound Analogue:DDC Unbound
1fm8B02 Unbound Unbound Unbound Unbound Analogue:DDC Unbound
1jepA02 Unbound Unbound Unbound Unbound Analogue:DFL Unbound
1jepB02 Unbound Unbound Unbound Unbound Analogue:DFL Unbound
1jx0A02 Unbound Unbound Unbound Unbound Unbound Bound:DFV
1jx0B02 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1A02 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1B02 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1C02 Unbound Unbound Unbound Unbound Unbound Bound:DFV
1jx1D02 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1E02 Unbound Unbound Unbound Unbound Unbound Unbound
1jx1F02 Unbound Unbound Unbound Unbound Unbound Unbound

Reference for Active-site residues
resource references E.C.
literature [6], [8] & [13]

Active-site residues
PDB Catalytic residues Cofactor-binding residues Modified residues Main-chain involved in catalysis Comment
1eypA01
1eypB01
1eyqA01
1eyqB01
1fm7A01
1fm7B01
1fm8A01
1fm8B01
1jepA01
1jepB01
1jx0A01
1jx0B01
1jx1A01
1jx1B01
1jx1C01
1jx1D01
1jx1E01
1jx1F01
1eypA02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1eypB02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1eyqA02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1eyqB02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1fm7A02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1fm7B02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1fm8A02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1fm8B02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1jepA02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1jepB02 THR 48;LYS 97;TYR 106;LYS 109;ASN 113;THR 190
1jx0A02 THR 48;LYS 97; ;LYS 109;ASN 113;THR 190 mutant Y106F
1jx0B02 THR 48;LYS 97; ;LYS 109;ASN 113;THR 190 mutant Y106F
1jx1A02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A
1jx1B02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A
1jx1C02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A
1jx1D02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A
1jx1E02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A
1jx1F02 ;LYS 97;TYR 106;LYS 109;ASN 113;THR 190 mutant T48A

References for Catalytic Mechanism
References Sections No. of steps in catalysis
[2]
SCHEME 2, p.396-398 1
[6]
Fig.4, p.788-789 2
[8]
Fig.5, p.5175-5176 2
[9]
Fig.1, p.1367-1369 2
[11]
Chart 1A
[13]
Scheme 1, p.2733 2

References
[1]
Resource
Comments
Medline ID
PubMed ID 2760066
Journal J Biol Chem
Year 1989
Volume 264
Pages 14272-6
Authors Bednar RA, Fried WB, Lock YW, Pramanik B
Title Chemical modification of chalcone isomerase by mercurials and tetrathionate. Evidence for a single cysteine residue in the active site.
Related PDB
Related UniProtKB
[2]
Resource
Comments
Medline ID
PubMed ID 2241159
Journal Arch Biochem Biophys
Year 1990
Volume 282
Pages 393-8
Authors Bednar RA, Adeniran AJ
Title Chemical modification of chalcone isomerase by diethyl pyrocarbonate: histidine residues are not essential for catalysis.
Related PDB
Related UniProtKB
[3]
Resource
Comments
Medline ID
PubMed ID 2340265
Journal Biochemistry
Year 1990
Volume 29
Pages 3684-90
Authors Bednar RA
Title Reactivity and pH dependence of thiol conjugation to N-ethylmaleimide: detection of a conformational change in chalcone isomerase.
Related PDB
Related UniProtKB
[4]
Resource
Comments
Medline ID
PubMed ID 1772902
Journal Bioconjug Chem
Year 1991
Volume 2
Pages 211-6
Authors Bednar RA, McCaffrey C, Shan K
Title Introduction of unnatural amino acids into chalcone isomerase.
Related PDB
Related UniProtKB
[5]
Resource
Comments
Medline ID
PubMed ID 11024274
Journal Gene
Year 2000
Volume 255
Pages 127-38
Authors Saslowsky DE, Dana CD, Winkel-Shirley B
Title An allelic series for the chalcone synthase locus in Arabidopsis.
Related PDB
Related UniProtKB
[6]
Resource
Comments X-ray crystallography
Medline ID
PubMed ID 10966651
Journal Nat Struct Biol
Year 2000
Volume 7
Pages 786-91
Authors Jez JM, Bowman ME, Dixon RA, Noel JP
Title Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase.
Related PDB 1eyp 1eyq
Related UniProtKB
[7]
Resource
Comments
Medline ID
PubMed ID 11553733
Journal Plant Physiol
Year 2001
Volume 127
Pages 46-57
Authors Dong X, Braun EL, Grotewold E
Title Functional conservation of plant secondary metabolic enzymes revealed by complementation of Arabidopsis flavonoid mutants with maize genes.
Related PDB
Related UniProtKB
[8]
Resource
Comments X-ray crystallography
Medline ID
PubMed ID 11955065
Journal Biochemistry
Year 2002
Volume 41
Pages 5168-76
Authors Jez JM, Bowman ME, Noel JP
Title Role of hydrogen bonds in the reaction mechanism of chalcone isomerase.
Related PDB 1jx0 1jx1
Related UniProtKB
[9]
Resource
Comments X-ray crystallography
Medline ID
PubMed ID 11698411
Journal J Biol Chem
Year 2002
Volume 277
Pages 1361-9
Authors Jez JM, Noel JP
Title Reaction mechanism of chalcone isomerase. pH dependence, diffusion control, and product binding differences.
Related PDB 1fm7 1fm8 1jep
Related UniProtKB
[10]
Resource
Comments
Medline ID
PubMed ID 12527208
Journal Gene
Year 2003
Volume 302
Pages 171-8
Authors Druka A, Kudrna D, Rostoks N, Brueggeman R, von Wettstein D, Kleinhofs A
Title Chalcone isomerase gene from rice (Oryza sativa) and barley (Hordeum vulgare): physical, genetic and mutation mapping.
Related PDB
Related UniProtKB
[11]
Resource
Comments
Medline ID
PubMed ID 12568595
Journal J Am Chem Soc
Year 2003
Volume 125
Pages 1472-3
Authors Hur S, Bruice TC
Title Enzymes do what is expected (chalcone isomerase versus chorismate mutase).
Related PDB
Related UniProtKB
[12]
Resource
Comments
Medline ID
PubMed ID 12644647
Journal Plant Physiol
Year 2003
Volume 131
Pages 941-51
Authors Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, Ayabe S
Title A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus.
Related PDB
Related UniProtKB
[13]
Resource
Comments
Medline ID
PubMed ID 14978275
Journal Proc Natl Acad Sci U S A
Year 2004
Volume 101
Pages 2730-5
Authors Hur S, Newby ZE, Bruice TC
Title Transition state stabilization by general acid catalysis, water expulsion, and enzyme reorganization in Medicago savita chalcone isomerase.
Related PDB
Related UniProtKB

Comments
This enzyme catalyzes intramolecular condensation.

Created Updated
2004-07-30 2009-02-26