spacer

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 M0168 and M0159

These two reactions have a combined similarity of 0.33


M0168

View
Comparison

M0159

View
EC 3.4.13.19
membrane dipeptidase
Sub-Class EC 3.1.8.1
aryldialkylphosphatase

Image of dipeptide

Image of water

right arrow

Image of amino acid

dipeptide
C00107
CHEBI:46761
water
C00001
CHEBI:15377
2 amino acid
C00045
CHEBI:59869
0.33

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



0.6956

Active Site



Catalytic Residues

Type Number Chain Location of Function
His 152 A Side Chain
Asp 288 A 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
zinc ZN 401 A
zinc ZN 402 A

Metal Cofactors

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

Reaction occurs across 3 steps

0.1948

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0168.stg01

Asp288 deprotonates the zinc activated water molecule.
0.33 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 M0168.stg02

The activated hydroxide attacks the peptide carbonyl in a nucleophilic addition.
0 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 M0168.stg03

The oxyanion initiates an elimination that cleaves the peptide bond, releasing the amino acid products, the N-terminus then protonates from Asp288
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.

spacer
spacer