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Overview for MACiE Entry M0319

Version history

General Information

EC Number: 1.6.99.1 (A member of the Oxidoreductases, Acting on NADH or NADPH, With other acceptors)

Enzyme Name: NADPH dehydrogenase

Biological Species: Saccharomyces pastorianus (Brewer's Yeast)

Catalytic Chain UniprotKB Accession Codes:

  • Q02899 - NADPH dehydrogenase 1

Representative PDB Code: 1oya - OLD YELLOW ENZYME AT 2 ANGSTROMS RESOLUTION: OVERALLSTRUCTURE, LIGAND BINDING AND COMPARISON WITH RELATEDFLAVOPROTEINS (Resolution = 2.00 Å).

Catalytic CATH Codes:

Display structure information

Overall Reaction:

Image of NADPH

Image of proton

Image of a,b - unsaturated ketone

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Image of ketone

Image of NADP

NADPH
C00005
CHEBI:16474
proton
C00080
CHEBI:24636
a,b - unsaturated ketone
X00138
ketone
X00139
CHEBI:3992
NADP
C00006
CHEBI:18009

Overall Comment: NADPH dehydrogenase, or old yellow enzyme (OYE), isolated from Candida albicans, is a NADPH oxidoreductase. Its FMN cofactor is reduced by NADPH, and in turn goes on to reduce the substrate. OYE is thought to be involved in general detoxification within the cell. This mechanism describes the reduction of an alpha,beta-unsaturated ketone.


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Stepwise Description of the Reaction

Step 1NADP reduces the FMN cofactor.
Step 2The anionic FMN intermediate acts as a hydride donor to the a-b unsaturated substrate. Tyr196 acts as the proton donor in the trans reduction of the substrate double bond.
Step 3The Tyr196A is reprotonated by a solvent molecule.

View similar reactions (composite manual annotation)


Catalytic Residues Involved

Type Number Chain Location of Function
His 191 A Side Chain
Asn 194 A Side Chain
Asn 251 A Side Chain
Tyr 196 A Side Chain
Thr 37 A Side Chain

Organic Cofactors for M0319

Type Identity Chain
FMN FMN 401 A Overview

References

  1. B. J. Brown et al. (2001), J. Biol. Chem., 277, 2138-2145. The role of glutamine 114 in old yellow enzyme.
    Medline: 11668181
  2. B. J. Brown et al. (1998), J. Biol. Chem., 273, 32753-32762. On the active site of Old Yellow Enzyme. Role of histidine 191 and asparagine 194.
    Medline: 9830019
  3. K. M. Fox et al. (1994), Structure, 2, 1089-1105. Old yellow enzyme at 2 A resolution: overall structure, ligand binding, and comparison with related flavoproteins.
    Medline: 7881908
  4. D. Xu et al. (1999), Proc. Natl Acad. Sci. USA, 96, 3556-3561. The role of threonine 37 in flavin reactivity of the old yellow enzyme.
    Medline: 10097075
  5. R. M. Kohli et al. (1998), J. Biol. Chem., 273, 32763-32770. The oxidative half-reaction of Old Yellow Enzyme. The role of tyrosine 196.
    Medline: 9830020

Homologue information for M0319 (1oya)

CSA Homologues

MACiE Homologues (within the PDB)

MACiE Homologues (within UniprotKB/SwissProt)



Entries with at least one Catalytic CATH code in common (different mechanisms):

MACiE Entry Enzyme Name
EC Number
PDB code CATH code Composite
Reaction Similarity
Catalytic Machinery
Similarity
M0102 L-lactate dehydrogenase (cytochrome)
1.1.2.3
1fcb 3.20.20.70
0.52270.2414Compare
M0108 2,4-dienoyl-CoA reductase (NADPH)
1.3.1.34
1ps9 3.20.20.70
0.50510.18Compare
M0109 dihydroorotate oxidase
1.3.3.1
1d3g 3.20.20.70
0.60860.09Compare
M0111 glutamate synthase (ferredoxin)
1.4.7.1
1ofd 3.20.20.70
0.26410.1205Compare
M0114 trimethylamine dehydrogenase
1.5.8.2
2tmd 3.20.20.70
0.57890.225Compare
M0148 transaldolase
2.2.1.2
1onr 3.20.20.70
0.15570.1053Compare
M0008 nicotinate-nucleotide diphosphorylase (carboxylating)
2.4.2.19
1qpr 3.20.20.70
0.19140Compare
M0243 pyridoxine 5'-phosphate synthase
2.6.99.2
1ho1 3.20.20.70
0.18380.2825Compare
M0050 orotidine-5'-phosphate decarboxylase
4.1.1.23
1dbt 3.20.20.70
0.05260Compare
M0252 indole-3-glycerol-phosphate synthase
4.1.1.48
1igs 3.20.20.70
0.2380.1199Compare
M0236 3-dehydro-L-gulonate-6-phosphate decarboxylase
4.1.1.85
1q6l 3.20.20.70
0.37140.09Compare
M0052 fructose-bisphosphate aldolase (Class II)
4.1.2.13
1b57 3.20.20.70
0.33330.2399Compare
M0222 fructose-bisphosphate aldolase (Class I)
4.1.2.13
2qut 3.20.20.70
0.13080.0529Compare
M0054 3-dehydroquinate dehydratase (type I)
4.2.1.10
1qfe 3.20.20.70
0.19080.0999Compare
M0230 porphobilinogen synthase
4.2.1.24
1gzg 3.20.20.70
0.20770Compare
M0267 dihydrodipicolinate synthase
4.2.1.52
1dhp 3.20.20.70
0.30660.0999Compare
M0270 ribulose-phosphate 3-epimerase
5.1.3.1
1h1z 3.20.20.70
0.37140.0185Compare
M0324 triosephosphate isomerase
5.3.1.1
1tph 3.20.20.70
0.34880.09Compare
M0223 pyruvate carboxylase
6.4.1.1
2qf7 3.20.20.70
0.20Compare

View a comparison of the other reactions in MACiE with the CATH domain 3.20.20.70


Links to this entry in other databases

Link to EC-PDB-SUM Link to PDB-SUM Link to RCSB PDB Link to PDBe Link to CSA
Link to MetaCyc Link to KEGG Link to BRENDA Link to ExplorENZ
Link to EzCatDB

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catalytic activity (molecular function)
NADPH dehydrogenase activity (molecular function)
metabolic process (biological process)
FMN binding (molecular function)
oxidoreductase activity (molecular function)
pentaerythritol trinitrate reductase activity (molecular function)
trichloro-p-hydroquinone reductive dehalogenase activity (molecular function)
oxidation-reduction process (biological process)
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