DB code: D00411
| CATH domain | 3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 | Catalytic domain |
|---|---|---|
| 3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 | Catalytic domain | |
| E.C. | 2.3.1.74 | |
| CSA | 1cgk | |
| M-CSA | 1cgk | |
| MACiE | ||
| CATH domain | Related DB codes (homologues) |
|---|---|
| 3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 | D00090 D00509 D00825 D00826 D00867 D00871 |
| Uniprot Enzyme Name | UniprotKB | Protein name | Synonyms | Pfam |
|---|---|---|---|
| P30074 |
Chalcone synthase 2
|
EC
2.3.1.74
Naringenin-chalcone synthase 2 |
PF02797
(Chal_sti_synt_C)
PF00195 (Chal_sti_synt_N) [Graphical View] |
| KEGG enzyme name |
|---|
|
naringenin-chalcone synthase
chalcone synthase flavanone synthase 6'-deoxychalcone synthase chalcone synthetase DOCS CHS |
| UniprotKB: Accession Number | Entry name | Activity | Subunit | Subcellular location | Cofactor |
|---|---|---|---|---|---|
| P30074 | CHS2_MEDSA | 3 malonyl-CoA + 4-coumaroyl-CoA = 4 CoA + naringenin chalcone + 3 CO(2). |
| KEGG Pathways | Map code | Pathways | E.C. |
|---|---|---|
| MAP00941 | Flavonoid biosynthesis |
| Compound table | |||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Substrates | Products | Intermediates | |||||||||||||||||
| KEGG-id | C00083 | C00223 | C00010 | C06561 | C00011 | ||||||||||||||
| E.C. | |||||||||||||||||||
| Compound | Malonyl-CoA | 4-Coumaroyl-CoA | CoA | Naringenin chalcone | CO2 | Monoketide intermediate | Enolic acetyl-CoA | Diketide CoA thioester | Diketide intermediate | Triketide CoA thioester | Triketide intermediate | Tetraketide CoA thioester | Tetraketide intermediate | Cyclized tetraketide | |||||
| Type | amine group,carbohydrate,carboxyl group,nucleotide ,peptide/protein,sulfide group | amine group,aromatic ring (only carbon atom),carbohydrate,nucleotide ,peptide/protein,sulfide group | amine group,carbohydrate,nucleotide ,peptide/protein,sulfhydryl group | aromatic ring (only carbon atom),carbohydrate | others | ||||||||||||||
| ChEBI |
15531 15531 |
85531 85531 |
15346 15346 |
15413 15413 |
16526 16526 |
||||||||||||||
| PubChem |
10663 644066 10663 644066 |
5280329 6440013 5280329 6440013 |
6816 87642 6816 87642 |
5280960 5280960 |
280 280 |
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| 1bi5A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1bq6A01 |
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Unbound | Unbound | Bound:COA | Unbound | Unbound | Unbound | ||||||||
| 1cgkA01 |
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Unbound | Unbound | Unbound | Analogue:NAR | Unbound | Unbound | ||||||||
| 1cgzA01 |
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Unbound | Unbound | Unbound | Analogue:STL | Unbound | Unbound | ||||||||
| 1chwA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1chwB01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1cmlA01 |
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Analogue:MLC | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:PIN | ||||||||
| 1d6fA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6hA01 |
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Unbound | Unbound | Bound:COA | Unbound | Unbound | Unbound | ||||||||
| 1d6iA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6iB01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i86A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i88A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i88B01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i89A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i89B01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i8bA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i8bB01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1jwxA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0vA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0vB01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0wA01 |
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Unbound | Unbound | Unbound | Analogue:STL | Unbound | Unbound | ||||||||
| 1u0wB01 |
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Unbound | Unbound | Unbound | Analogue:STL | Unbound | Unbound | ||||||||
| 1u0wC01 |
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Unbound | Unbound | Unbound | Analogue:STL | Unbound | Unbound | ||||||||
| 1u0wD01 |
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Unbound | Unbound | Unbound | Analogue:STL | Unbound | Unbound | ||||||||
| 1bi5A02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1bq6A02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1cgkA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1cgzA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1chwA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1chwB02 |
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Unbound | Analogue:HXC | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1cmlA02 |
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Unbound | Analogue:HXC | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6fA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6hA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6iA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1d6iB02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i86A02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i88A02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i88B02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i89A02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i89B02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i8bA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1i8bB02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1jwxA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0vA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0vB02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0wA02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0wB02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0wC02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| 1u0wD02 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound | ||||||||
| Reference for Active-site residues | ||
|---|---|---|
| resource | references | E.C. |
| PDB;1bi5, 1bq6, 1cgk, 1cgz, 1chw & Swiss-prot;P48391 | ||
| Active-site residues | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| PDB | Catalytic residues | Cofactor-binding residues | Modified residues | Main-chain involved in catalysis | Comment | |||||
| 1bi5A01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1bq6A01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1cgkA01 |
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CYS 164;PHE 215 | ||||
| 1cgzA01 |
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CYS 164;PHE 215 | ||||
| 1chwA01 |
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;PHE 215 | mutant C164S | |||
| 1chwB01 |
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;PHE 215 | mutant C164S | |||
| 1cmlA01 |
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;PHE 215 | mutant C164A | |||
| 1d6fA01 |
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;PHE 215 | mutant C164A | |||
| 1d6hA01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1d6iA01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1d6iB01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i86A01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i88A01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i88B01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i89A01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i89B01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i8bA01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1i8bB01 |
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;PHE 215 | CSD 164(S-sulfinocysteine) | |||
| 1jwxA01 |
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; | CSD 164(S-sulfinocysteine) | mutant F215S | ||
| 1u0vA01 |
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CYS 164;PHE 215 | ||||
| 1u0vB01 |
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CYS 164;PHE 215 | ||||
| 1u0wA01 |
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CYS 164;PHE 215 | ||||
| 1u0wB01 |
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CYS 164;PHE 215 | ||||
| 1u0wC01 |
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CYS 164;PHE 215 | ||||
| 1u0wD01 |
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CYS 164;PHE 215 | ||||
| 1bi5A02 |
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HIS 303;ASN 336 | ||||
| 1bq6A02 |
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HIS 303;ASN 336 | ||||
| 1cgkA02 |
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HIS 303;ASN 336 | ||||
| 1cgzA02 |
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HIS 303;ASN 336 | ||||
| 1chwA02 |
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HIS 303;ASN 336 | ||||
| 1chwB02 |
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HIS 303;ASN 336 | ||||
| 1cmlA02 |
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HIS 303;ASN 336 | ||||
| 1d6fA02 |
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HIS 303;ASN 336 | ||||
| 1d6hA02 |
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HIS 303; | mutant N336A | |||
| 1d6iA02 |
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;ASN 336 | mutant H303Q | |||
| 1d6iB02 |
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;ASN 336 | mutant H303Q | |||
| 1i86A02 |
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HIS 303;ASN 336 | ||||
| 1i88A02 |
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HIS 303;ASN 336 | ||||
| 1i88B02 |
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HIS 303;ASN 336 | ||||
| 1i89A02 |
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HIS 303;ASN 336 | ||||
| 1i89B02 |
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HIS 303;ASN 336 | ||||
| 1i8bA02 |
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HIS 303;ASN 336 | ||||
| 1i8bB02 |
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HIS 303;ASN 336 | ||||
| 1jwxA02 |
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HIS 303;ASN 336 | ||||
| 1u0vA02 |
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HIS 303;ASN 336 | ||||
| 1u0vB02 |
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HIS 303;ASN 336 | ||||
| 1u0wA02 |
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HIS 303;ASN 336 | ||||
| 1u0wB02 |
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HIS 303;ASN 336 | ||||
| 1u0wC02 |
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HIS 303;ASN 336 | ||||
| 1u0wD02 |
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HIS 303;ASN 336 | ||||
| References for Catalytic Mechanism | ||
|---|---|---|
| References | Sections | No. of steps in catalysis |
|
[5]
|
Fig.6, p.778-782 | 8 |
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[6]
|
Fig.1, p.39642-39645 | 2 |
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[7]
|
Fig.1, Fig.9, p.898-900 | 2 |
|
[9]
|
Fig.4, p.394-397 | 2 |
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[11]
|
Fig.1, p.14836-14387 | 4 |
|
[14]
|
Fig.1, Fig.6, p.45169-45174 | |
|
[15]
|
Fig.1, Fig.5, Fig.6 | |
| References | |
|---|---|
| [1] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 6853502 |
| Journal | J Biol Chem |
| Year | 1983 |
| Volume | 258 |
| Pages | 6730-4 |
| Authors | Schuz R, Heller W, Hahlbrock K |
| Title |
Substrate specificity of chalcone synthase from Petroselinum hortense. |
| Related PDB | |
| Related UniProtKB | |
| [2] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 3777940 |
| Journal | Arch Biochem Biophys |
| Year | 1986 |
| Volume | 250 |
| Pages | 364-72 |
| Authors | Knogge W, Schmelzer E, Weissenbock G |
| Title | The role of chalcone synthase in the regulation of flavonoid biosynthesis in developing oat primary leaves. |
| Related PDB | |
| Related UniProtKB | |
| [3] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 7713888 |
| Journal | J Biol Chem |
| Year | 1995 |
| Volume | 270 |
| Pages | 7922-8 |
| Authors | Tropf S, Karcher B, Schroder G, Schroder J |
| Title |
Reaction mechanisms of homodimeric plant polyketide synthase (stilbenes and chalcone synthase). |
| Related PDB | |
| Related UniProtKB | |
| [4] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 10476972 |
| Journal | Nature |
| Year | 1999 |
| Volume | 400 |
| Pages | 897-9 |
| Authors | Funa N, Ohnishi Y, Fujii I, Shibuya M, Ebizuka Y, Horinouchi S |
| Title | A new pathway for polyketide synthesis in microorganisms. |
| Related PDB | |
| Related UniProtKB | |
| [5] | |
| Resource | |
| Comments | X-ray crystallography |
| Medline ID | |
| PubMed ID | 10426957 |
| Journal | Nat Struct Biol |
| Year | 1999 |
| Volume | 6 |
| Pages | 775-84 |
| Authors | Ferrer JL, Jez JM, Bowman ME, Dixon RA, Noel JP |
| Title | Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis. |
| Related PDB | 1bi5 1bq6 1cgk 1cgz 1chw 1cml |
| Related UniProtKB | |
| [6] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 11006298 |
| Journal | J Biol Chem |
| Year | 2000 |
| Volume | 275 |
| Pages | 39640-6 |
| Authors | Jez JM, Noel JP |
| Title |
Mechanism of chalcone synthase. |
| Related PDB | |
| Related UniProtKB | |
| [7] | |
| Resource | |
| Comments | X-RAY CRYSTALLOGRAPHY (1.69 ANGSTROMS) |
| Medline ID | 20120577 |
| PubMed ID | 10653632 |
| Journal | Biochemistry |
| Year | 2000 |
| Volume | 39 |
| Pages | 890-902 |
| Authors | Jez JM, Ferrer JL, Bowman ME, Dixon RA, Noel JP |
| Title | Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase. |
| Related PDB | 1d6f 1d6h 1d6i |
| Related UniProtKB | P30074 |
| [8] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 10973790 |
| Journal | Biochem Biophys Res Commun |
| Year | 2000 |
| Volume | 275 |
| Pages | 725-30 |
| Authors | Suh DY, Kagami J, Fukuma K, Sankawa U |
| Title | Evidence for catalytic cysteine-histidine dyad in chalcone synthase. |
| Related PDB | |
| Related UniProtKB | |
| [9] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 11774005 |
| Journal | J Ind Microbiol Biotechnol |
| Year | 2001 |
| Volume | 27 |
| Pages | 393-8 |
| Authors | Jez JM, Ferrer JL, Bowman ME, Austin MB, Schroder J, Dixon RA, Noel JP |
| Title | Structure and mechanism of chalcone synthase-like polyketide synthases. |
| Related PDB | |
| Related UniProtKB | |
| [10] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 11728463 |
| Journal | FEBS Lett |
| Year | 2001 |
| Volume | 508 |
| Pages | 413-7 |
| Authors | Lukacin R, Schreiner S, Matern U |
| Title | Transformation of acridone synthase to chalcone synthase. |
| Related PDB | |
| Related UniProtKB | |
| [11] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 11732902 |
| Journal | Biochemistry |
| Year | 2001 |
| Volume | 40 |
| Pages | 14829-38 |
| Authors | Jez JM, Bowman ME, Noel JP |
| Title | Structure-guided programming of polyketide chain-length determination in chalcone synthase. |
| Related PDB | 1i86 1i88 1i89 1i8b |
| Related UniProtKB | |
| [12] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 11959984 |
| Journal | Proc Natl Acad Sci U S A |
| Year | 2002 |
| Volume | 99 |
| Pages | 5319-24 |
| Authors | Jez JM, Bowman ME, Noel JP |
| Title | Expanding the biosynthetic repertoire of plant type III polyketide synthases by altering starter molecule specificity. |
| Related PDB | 1jwx |
| Related UniProtKB | |
| [13] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 12502351 |
| Journal | J Nat Prod |
| Year | 2002 |
| Volume | 65 |
| Pages | 1956-62 |
| Authors | Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP |
| Title | Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone. |
| Related PDB | |
| Related UniProtKB | |
| [14] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15265863 |
| Journal | J Biol Chem |
| Year | 2004 |
| Volume | 279 |
| Pages | 45162-74 |
| Authors | Austin MB, Izumikawa M, Bowman ME, Udwary DW, Ferrer JL, Moore BS, Noel JP |
| Title | Crystal structure of a bacterial type III polyketide synthase and enzymatic control of reactive polyketide intermediates. |
| Related PDB | |
| Related UniProtKB | |
| [15] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15380179 |
| Journal | Chem Biol |
| Year | 2004 |
| Volume | 11 |
| Pages | 1179-94 |
| Authors | Austin MB, Bowman ME, Ferrer JL, Schroder J, Noel JP |
| Title | An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases. |
| Related PDB | 1u0v 1u0w |
| Related UniProtKB | |
| Comments |
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According to the literature [5], (A) Transfer of acyl group from sulfur atom of coumaronyl-CoA to the nucleophilic cysteine residue, (B) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, (C) Transfer of acyl group (monoketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, (D) Transfer of acyl group (diketide) from sulfur atom of diketide CoA thioester to the cysteine residue, (E) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, (F) Transfer of acyl group (diketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, (G) Transfer of acyl group (triketide) from sulfur atom of triketide CoA thioester to the cysteine residue, (H) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, (I) Transfer of acyl group (triketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, (J) Transfer of acyl group (tetraketide) from sulfur atom of triketide CoA thioester to the cysteine residue, (K) Intramolecular transfer of acyl group from the cysteine to the methylene carbon of the tetraketide intermediate (Cyclization): (L) Isomerization of carbonyl oxygen to hydroxyl oxygen (Aromatization): |
| Created | Updated |
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| 2002-11-25 | 2009-02-26 |