DB code: D00447
| CATH domain | 3.10.180.10 : 2,3-Dihydroxybiphenyl 1,2-Dioxygenase; domain 1 | |
|---|---|---|
| 3.10.180.10 : 2,3-Dihydroxybiphenyl 1,2-Dioxygenase; domain 1 | Catalytic domain | |
| E.C. | 1.13.11.27 | |
| CSA | ||
| M-CSA | ||
| MACiE | ||
| CATH domain | Related DB codes (homologues) |
|---|---|
| 3.10.180.10 : 2,3-Dihydroxybiphenyl 1,2-Dioxygenase; domain 1 | D00446 D00448 S00540 S00185 |
| Uniprot Enzyme Name | UniprotKB | Protein name | Synonyms | Pfam | RefSeq |
|---|---|---|---|---|
| P80064 |
4-hydroxyphenylpyruvate dioxygenase
|
HPPDase
4HPPD HPD EC 1.13.11.27 |
PF00903
(Glyoxalase)
[Graphical View] |
|
| Q53586 |
4-hydroxyphenylpyruvate dioxygenase
|
HPPDase
4HPPD HPD EC 1.13.11.27 |
PF00903
(Glyoxalase)
PF12681 (Glyoxalase_2) [Graphical View] |
NP_826326.1
(Protein)
NC_003155.4 (DNA/RNA sequence) |
| O48604 |
4-hydroxyphenylpyruvate dioxygenase
|
EC
1.13.11.27
4-hydroxyphenylpyruvic acid oxidase HPPDase 4HPPD HPD |
PF00903
(Glyoxalase)
[Graphical View] |
|
| P93836 |
4-hydroxyphenylpyruvate dioxygenase
|
EC
1.13.11.27
4-hydroxyphenylpyruvic acid oxidase HPPDase 4HPPD HPD |
PF00903
(Glyoxalase)
[Graphical View] |
NP_172144.2
(Protein)
NM_100536.3 (DNA/RNA sequence) |
| KEGG enzyme name |
|---|
|
4-hydroxyphenylpyruvate dioxygenase
p-hydroxyphenylpyruvic hydroxylase p-hydroxyphenylpyruvate hydroxylase p-hydroxyphenylpyruvate oxidase p-hydroxyphenylpyruvic oxidase p-hydroxyphenylpyruvate dioxygenase p-hydroxyphenylpyruvic acid hydroxylase 4-hydroxyphenylpyruvic acid dioxygenase |
| UniprotKB: Accession Number | Entry name | Activity | Subunit | Subcellular location | Cofactor |
|---|---|---|---|---|---|
| P80064 | HPPD_PSEUJ | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | Homotetramer. | Binds 1 iron ion per subunit. | |
| Q53586 | HPPD_STRAW | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | Homodimer. | Binds 1 iron ion per subunit. | |
| O48604 | HPPD_HORVU | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | Cytoplasm (By similarity). | Binds 1 iron ion per subunit (By similarity). | |
| P93836 | HPPD_ARATH | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | Homodimer. | Cytoplasm. | Binds 1 iron ion per subunit. |
| KEGG Pathways | Map code | Pathways | E.C. |
|---|---|---|
| MAP00350 | Tyrosine metabolism | |
| MAP00360 | Phenylalanine metabolism |
| Compound table | |||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Cofactors | Substrates | Products | Intermediates | ||||||||
| KEGG-id | C00023 | C00007 | C01179 | C00011 | C00544 | ||||||
| E.C. | |||||||||||
| Compound | Iron | O2 | 3-(4-Hydroxyphenyl)pyruvate | CO2 | Homogentisate | ||||||
| Type | heavy metal | others | aromatic ring (only carbon atom),carbohydrate,carboxyl group | others | aromatic ring (only carbon atom),carboxyl group | ||||||
| ChEBI |
18248 82664 18248 82664 |
15379 26689 27140 15379 26689 27140 |
15999 15999 |
16526 16526 |
44747 44747 |
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| PubChem |
23925 23925 |
977 977 |
979 979 |
280 280 |
780 780 |
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| 1cjxA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1cjxB01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1cjxC01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1cjxD01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1t47A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1t47B01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8B01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8C01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8D01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp9A01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp9B01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sqdA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1tfzA01 |
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Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1cjxA02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
| 1cjxB02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
| 1cjxC02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
| 1cjxD02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
| 1t47A02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-NTD |
| 1t47B02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-NTD |
| 1sp8A02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8B02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8C02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp8D02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp9A02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sp9B02 |
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Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1sqdA02 |
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Bound:_FE | Unbound | Unbound | Unbound | Unbound | Unbound |
| 1tfzA02 |
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Bound:_FE | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:_FE-869 |
| Reference for Active-site residues | ||
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| resource | references | E.C. |
| PDB;1cjx | ||
| Active-site residues | ||||||||||
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| PDB | Catalytic residues | Cofactor-binding residues | Modified residues | Main-chain involved in catalysis | Comment | |||||
| 1cjxA01 |
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| 1cjxB01 |
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| 1cjxC01 |
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| 1cjxD01 |
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| 1t47A01 |
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| 1t47B01 |
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| 1sp8A01 |
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| 1sp8B01 |
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| 1sp8C01 |
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| 1sp8D01 |
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| 1sp9A01 |
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| 1sp9B01 |
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| 1sqdA01 |
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| 1tfzA01 |
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| 1cjxA02 |
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HIS 161;HIS 240;GLU 322(Iron binding) | ||||
| 1cjxB02 |
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HIS 161;HIS 240;GLU 322(Iron binding) | ||||
| 1cjxC02 |
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HIS 161;HIS 240;GLU 322(Iron binding) | ||||
| 1cjxD02 |
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HIS 161;HIS 240;GLU 322(Iron binding) | ||||
| 1t47A02 |
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HIS 187;HIS 270;GLU 349(Iron binding) | ||||
| 1t47B02 |
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HIS 187;HIS 270;GLU 349(Iron binding) | ||||
| 1sp8A02 |
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HIS 219;HIS 301;GLU 387(Iron binding) | ||||
| 1sp8B02 |
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HIS 219;HIS 301;GLU 387(Iron binding) | ||||
| 1sp8C02 |
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HIS 219;HIS 301;GLU 387(Iron binding) | ||||
| 1sp8D02 |
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HIS 219;HIS 301;GLU 387(Iron binding) | ||||
| 1sp9A02 |
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HIS 226;HIS 308;GLU 394(Iron binding) | ||||
| 1sp9B02 |
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HIS 226;HIS 308;GLU 394(Iron binding) | ||||
| 1sqdA02 |
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HIS 205;HIS 287;GLU 373(Iron binding) | ||||
| 1tfzA02 |
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HIS 205;HIS 287;GLU 373(Iron binding) | ||||
| References for Catalytic Mechanism | ||
|---|---|---|
| References | Sections | No. of steps in catalysis |
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[2]
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Fig.4, Scheme I, p.3162-3164 | |
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[6]
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Scheme 1, Scheme 2, p.1459-1460 | |
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[7]
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p.979-981 | |
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[13]
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Scheme 2, Scheme 3, Scheme 4, p.12334-12336 | |
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[15]
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Scheme 2C, Scheme 3 | |
| References | |
|---|---|
| [1] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 7274212 |
| Journal | Eur J Biochem |
| Year | 1981 |
| Volume | 117 |
| Pages | 311-8 |
| Authors | Leinberger R, Hull WE, Simon H, Retey J |
| Title | Steric course of the NIH shift in the enzymic formation of homogentisic acid. |
| Related PDB | |
| Related UniProtKB | |
| [2] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 4027238 |
| Journal | Biochemistry |
| Year | 1985 |
| Volume | 24 |
| Pages | 3158-65 |
| Authors | Pascal RA Jr, Oliver MA, Chen YC |
| Title | Alternate substrates and inhibitors of bacterial 4-hydroxyphenylpyruvate dioxygenase. |
| Related PDB | |
| Related UniProtKB | |
| [3] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 3017941 |
| Journal | J Biol Chem |
| Year | 1986 |
| Volume | 261 |
| Pages | 11693-6 |
| Authors | Bradley FC, Lindstedt S, Lipscomb JD, Que L Jr, Roe AL, Rundgren M |
| Title | 4-Hydroxyphenylpyruvate dioxygenase is an iron-tyrosinate protein. |
| Related PDB | |
| Related UniProtKB | |
| [4] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 1572351 |
| Journal | Eur J Biochem |
| Year | 1992 |
| Volume | 205 |
| Pages | 459-66 |
| Authors | Ruetschi U, Odelhog B, Lindstedt S, Barros-Soderling J, Persson B, Jornvall H |
| Title |
Characterization of 4-hydroxyphenylpyruvate dioxygenase. |
| Related PDB | |
| Related UniProtKB | |
| [5] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 7597701 |
| Journal | Toxicol Appl Pharmacol |
| Year | 1995 |
| Volume | 133 |
| Pages | 12-9 |
| Authors | Ellis MK, Whitfield AC, Gowans LA, Auton TR, Provan WM, Lock EA, Smith LL |
| Title | Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione. |
| Related PDB | |
| Related UniProtKB | |
| [6] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 10465420 |
| Journal | Bioorg Med Chem |
| Year | 1999 |
| Volume | 7 |
| Pages | 1459-65 |
| Authors | Ling TS, Shiu S, Yang DY |
| Title | Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver. |
| Related PDB | |
| Related UniProtKB | |
| [7] | |
| Resource | |
| Comments | X-ray crystallography |
| Medline ID | |
| PubMed ID | 10467142 |
| Journal | Structure Fold Des |
| Year | 1999 |
| Volume | 7 |
| Pages | 977-88 |
| Authors | Serre L, Sailland A, Sy D, Boudec P, Rolland A, Pebay-Peyroula E, Cohen-Addad C |
| Title | Crystal structure of Pseudomonas fluorescens 4-hydroxyphenylpyruvate dioxygenase: an enzyme involved in the tyrosine degradation pathway. |
| Related PDB | 1cjx |
| Related UniProtKB | |
| [8] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 10853644 |
| Journal | Bioorg Med Chem Lett |
| Year | 2000 |
| Volume | 10 |
| Pages | 843-5 |
| Authors | Lin YL, Wu CS, Lin SW, Yang DY |
| Title | SAR studies of 2-o-substituted-benzoyl- and 2-alkanoyl-cyclohexane-1,3-diones as inhibitors of 4-hydroxyphenylpyruvate dioxygenase. |
| Related PDB | |
| Related UniProtKB | |
| [9] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 12067543 |
| Journal | Bioorg Med Chem Lett |
| Year | 2002 |
| Volume | 12 |
| Pages | 1709-13 |
| Authors | Lin YL, Huang JL, Wu CS, Liu HG, Yang DY |
| Title |
Design, |
| Related PDB | |
| Related UniProtKB | |
| [10] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 12014960 |
| Journal | J Med Chem |
| Year | 2002 |
| Volume | 45 |
| Pages | 2222-8 |
| Authors | Wu CS, Huang JL, Sun YS, Yang DY |
| Title | Mode of action of 4-hydroxyphenylpyruvate dioxygenase inhibition by triketone-type inhibitors. |
| Related PDB | |
| Related UniProtKB | |
| [11] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 12031447 |
| Journal | Phytochemistry |
| Year | 2002 |
| Volume | 60 |
| Pages | 281-8 |
| Authors | Meazza G, Scheffler BE, Tellez MR, Rimando AM, Romagni JG, Duke SO, Nanayakkara D, Khan IA, Abourashed EA, Dayan FE |
| Title | The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase. |
| Related PDB | |
| Related UniProtKB | |
| [12] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 12939152 |
| Journal | Biochemistry |
| Year | 2003 |
| Volume | 42 |
| Pages | 10238-45 |
| Authors | Kavana M, Moran GR |
| Title | Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione. |
| Related PDB | |
| Related UniProtKB | |
| [13] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15379572 |
| Journal | Biochemistry |
| Year | 2004 |
| Volume | 43 |
| Pages | 12331-42 |
| Authors | Borowski T, Bassan A, Siegbahn PE |
| Title | 4-Hydroxyphenylpyruvate dioxygenase: a hybrid density functional study of the catalytic reaction mechanism. |
| Related PDB | |
| Related UniProtKB | |
| [14] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15157070 |
| Journal | Biochemistry |
| Year | 2004 |
| Volume | 43 |
| Pages | 6370-7 |
| Authors | Brownlee JM, Johnson-Winters K, Harrison DH, Moran GR |
| Title |
Structure of the ferrous form of (4-hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, |
| Related PDB | 1t47 |
| Related UniProtKB | |
| [15] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 14730970 |
| Journal | Biochemistry |
| Year | 2004 |
| Volume | 43 |
| Pages | 663-74 |
| Authors | Gunsior M, Ravel J, Challis GL, Townsend CA |
| Title | Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation. |
| Related PDB | |
| Related UniProtKB | |
| [16] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15301540 |
| Journal | Biochemistry |
| Year | 2004 |
| Volume | 43 |
| Pages | 10414-23 |
| Authors | Yang C, Pflugrath JW, Camper DL, Foster ML, Pernich DJ, Walsh TA |
| Title | Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases. |
| Related PDB | 1sqd 1tfz |
| Related UniProtKB | |
| [17] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15070344 |
| Journal | J Am Chem Soc |
| Year | 2004 |
| Volume | 126 |
| Pages | 4486-7 |
| Authors | Neidig ML, Kavana M, Moran GR, Solomon EI |
| Title | CD and MCD studies of the non-heme ferrous active site in (4-hydroxyphenyl)pyruvate dioxygenase: correlation between oxygen activation in the extradiol and alpha-KG-dependent dioxygenases. |
| Related PDB | |
| Related UniProtKB | |
| [18] | |
| Resource | |
| Comments | |
| Medline ID | |
| PubMed ID | 15084729 |
| Journal | Plant Physiol |
| Year | 2004 |
| Volume | 134 |
| Pages | 1388-400 |
| Authors | Fritze IM, Linden L, Freigang J, Auerbach G, Huber R, Steinbacher S |
| Title | The crystal structures of Zea mays and Arabidopsis 4-hydroxyphenylpyruvate dioxygenase. |
| Related PDB | 1sp8 1sp9 |
| Related UniProtKB | |
| Comments |
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| Created | Updated |
|---|---|
| 2004-10-28 | 2009-09-29 |