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The two reactions compared are done so using a Tanimoto similarity score (for more information, please see the MACiE FAQ) for the bond changes only. The score maay range from 0 to 1 where 1 indicates that the two reactions are identical at the bond change level and 0 indicates that there are no bond changes in common.


Key

1.0-0.9 0.9-0.8 0.8-0.7 0.7-0.6 0.6-0.5 0.5-0.4 0.4-0.3 0.3-0.2 0.2-0.1 0.1-0.0 =0

Results for Comparison of M0131 and M0123

These two reactions have a combined similarity of 0.08


M0131

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Comparison

M0123

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EC 1.14.13.2
4-hydroxybenzoate 3-monooxygenase
Sub-Class EC 1.8.99.2
adenylyl-sulfate reductase

Image of NADPH

Image of oxygen

Image of 4-hydroxybenzoate

right arrow

Image of NADP

Image of water

Image of 3,4-dihydroxybenzoate

NADPH
C00005
CHEBI:16474
oxygen
C00007
CHEBI:15379
4-hydroxybenzoate
C00156
CHEBI:17879
NADP
C00006
CHEBI:18009
water
C00001
CHEBI:15377
3,4-dihydroxybenzoate
C00230
CHEBI:36241
0.15

Image of double-electron donor

Image of proton

Image of adenylylsulphate

right arrow

Image of AMP

Image of sulphite

Image of oxidised donor

double-electron donor
X00054
proton
C00080
CHEBI:24636
adenylylsulphate
C00224
CHEBI:58243
AMP
C00020
CHEBI:456215
sulphite
C00094
CHEBI:17137
oxidised donor
C02177

Catalytic CATH Codes

3.50.50.60
3.30.9.10

Catalytic CATH Codes

3.50.50.60
3.90.700.10
3.30.70.20

Active Site



0.06305

Active Site



Catalytic Residues

Type Number Chain Location of Function
His 72 A Side Chain
Tyr 201 A Side Chain
Pro 293 A Main Chain Carbonyl
Lys 297 A Side Chain
Tyr 385 A Side Chain
0.0625

Catalytic Residues

Type Number Chain Location of Function
Asn 74 A Side Chain
Main Chain Amide
Glu 141 A Side Chain
Trp 234 A Side Chain
Arg 265 A Side Chain
Asp 361 A Side Chain
His 398 A Side Chain
Ser 449 A Side Chain
Main Chain Amide
Trp 48 B Side Chain

Organic Cofactors

Type Identity Chain
FAD FAD 395

Organic Cofactors

Type Identity Chain
FAD FAD 1000 A

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

Type Het group Number Chain
iron SF4 1110 B
iron SF4 1100 B

Reaction occurs across 9 steps

0.088

Reaction occurs across 5 steps

Step 1
GIF of Reaction Step M0131.stg01

In a proton transfer chain involving His72-water-water-Tyr385-Tyr201 water deprotonates the 4-hydroxybenzoate substrate.
0.14 Step 1
GIF of Reaction Step M0123.stg01

A single electron is transferred from the donor, through two iron-sulfur clusters and Trp48B to FAD, with concomitant deprotonation of water.
Step 2
GIF of Reaction Step M0131.stg02

A conformational change allows NADP to bind, which initiates a reverse of the first proton transfer and a hydride transfer from NADP to the FAD cofactor.
0.07 Step 2
GIF of Reaction Step M0123.stg02

A second single electron is transferred from the donor, through two iron-sulfur clusters and Trp48B to FAD forming the N1 anion form of reduced FAD.
Step 3
GIF of Reaction Step M0131.stg03

FAD undergoes a double bond rearrangement that results in the single electron transfer from FAD to dioxygen.
0 Step 3
GIF of Reaction Step M0123.stg03

The N5 of FAD initiates a nucleophilic attack on the sulfur of the sulfate group in an addition reaction.
Step 4
GIF of Reaction Step M0131.stg04

The FAD and dioxygen radical species undergo a colligation reaction to form the FAD-peroxo adduct.
0 Step 4
GIF of Reaction Step M0123.stg04

Water deprotonates the N5 of FAD. One of the oxygen anions of sulfate eliminates the phosphate group.
Step 5
GIF of Reaction Step M0131.stg05

The FAD-peroxo adduct deprotonates a water molecule.
0.25 Step 5
GIF of Reaction Step M0123.stg05

The N5 of FAD initiates the elimination of the sulfite with concomitant deprotonation of water.
Step 6
GIF of Reaction Step M0131.stg06

In a proton transfer chain involving His72-water-water-Tyr385-Tyr201 water deprotonates the 4-hydroxybenzoate substrate. The substrate undergoes a double bond rearrangement that results in the ortho-position attacking the FAD-peroxo adduct in a nucleophilic substitution that cleaves the O-O bond.
N/A Step 6
No Step with this number present
Step 7
GIF of Reaction Step M0131.stg07

The FAD intermediate deprotonates the hydorxylated aromatic intermediate, cleaving the C-H bond and initiating a double bond rearrangement to yield 3,4-dihydroxybenzoic acid. This then takes a proton from water through the His72-water-water-Tyr385-Tyr201 proton transfer chain.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0131.stg08

Water deprotonates the 3,4-dihydroxybenzoic acid through the His72-water-water-Tyr385-Tyr201 proton transfer chain.
N/A Step 8
No Step with this number present
Step 9
GIF of Reaction Step M0131.stg09

The FAD-bound hydroxyl group initiates an intramolecular elimination of water, regenerating the FAD cofactor.
N/A Step 9
No Step with this number present

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