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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 M0087 and M0159

These two reactions have a combined similarity of 0.30


M0087

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Comparison

M0159

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EC 3.5.1.5
urease
Sub-Class EC 3.1.8.1
aryldialkylphosphatase

Image of urea

Image of water

right arrow

Image of carbon dioxide

Image of ammonia

urea
C00086
CHEBI:16199
water
C00001
CHEBI:15377
carbon dioxide
C00011
CHEBI:16526
2 ammonia
C00014
CHEBI:16134
0.26

Image of aryl dialkyl phosphate

Image of water

right arrow

Image of proton

Image of dialkyl phosphate

Image of aryl alcohol

aryl dialkyl phosphate
C03254
CHEBI:37558
water
C00001
CHEBI:15377
2 proton
C00080
CHEBI:24636
dialkyl phosphate
C02534
CHEBI:16648
aryl alcohol
X00137

Catalytic CATH Codes

3.20.20.140

Catalytic CATH Codes

3.20.20.140

Active Site



0.6906

Active Site



Catalytic Residues

Type Number Chain Location of Function
Kcx 217 C Post-translationally modified residue
His 219 C Side Chain
Asp 221 C Side Chain
His 320 C Side Chain
Arg 336 C Side Chain
Asp 360 C Side Chain
0.75

Catalytic Residues

Type Number Chain Location of Function
Asp 233 A Side Chain
His 254 A Side Chain
Asp 301 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
nickel NI 574 x
nickel NI 575 x

Metal Cofactors

Type Het group Number Chain
zinc ZN 401 A
zinc ZN 402 A

Reaction occurs across 3 steps

0.1704

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0087.stg01

His320 deprotonates nickel bound water, which initiates a nucleophilic attack on the nickel bound urea in an addition reaction.
0.11 Step 1
GIF of Reaction Step M0159.stg01

Asp301 undergoes an isomerisation to deprotonate a zinc activated water, which attacks the phosphate of the aryl dialkyl phosphate in a nucleophilic substitution that releases the aryl alcohol product and the dialkyl phosphate coordinated to the active site zinc ions.
Step 2
GIF of Reaction Step M0087.stg02

The tetrahedral intermediate collapses, eliminating ammonia with concomitant deprotonation of His320.
0.25 Step 2
GIF of Reaction Step M0159.stg02

Asp233 deprotonates His254 which deprotonates Asp301 and the dialkyl phosphate product dissociates from the active site.
Step 3
GIF of Reaction Step M0087.stg03

Carbamate dissociates from the active site and is spontaneously converted to carbon dioxide and a second molecule of ammonia
0.2 Step 3
GIF of Reaction Step M0159.stg03

Water deprotonates Asp233
Step 4
No Step with this number present
N/A Step 4
GIF of Reaction Step M0159.stg04

Asp301 deprotonates a zinc activate water molecule
Step 5
No Step with this number present
N/A Step 5
GIF of Reaction Step M0159.stg05

Asp233 deprotonates Hi254 which deprotonates Asp301.
Step 6
No Step with this number present
N/A Step 6
GIF of Reaction Step M0159.stg06

Water deprotonates Asp233, regenerating the active site.

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