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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 M0181 and M0036

These two reactions have a combined similarity of 0.29


M0181

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Comparison

M0036

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EC 3.11.1.1
phosphonoacetaldehyde hydrolase
Sub-Class EC 3.8.1.2
(S)-2-haloacid dehalogenase

Image of phosphonoacetaldehyde

Image of water

right arrow

Image of phosphate

Image of acetaldehyde

phosphonoacetaldehyde
C03167
CHEBI:18124
water
C00001
CHEBI:15377
phosphate
C00009
CHEBI:18367
acetaldehyde
C00084
CHEBI:15343
0.14

Image of 2-chloropropionate

Image of water

right arrow

Image of proton

Image of chloride ion

Image of (S)-lactate

2-chloropropionate
X00012
water
C00001
CHEBI:15377
proton
C00080
CHEBI:24636
chloride ion
C00698
CHEBI:17996
(S)-lactate
C00186
CHEBI:16651

Catalytic CATH Codes

3.40.50.1000
1.10.150.240

Catalytic CATH Codes

3.40.50.1000
1.10.150.240

Active Site



0.24554

Active Site



Catalytic Residues

Type Number Chain Location of Function
Asp 12 A Side Chain
Ala 45 A Main Chain Carbonyl
Met 49 A Side Chain
Lys 53 A Side Chain
His 56 A Side Chain
Arg 160 A Side Chain
0.2666

Catalytic Residues

Type Number Chain Location of Function
Asp 8 A Side Chain
Thr 12 A Side Chain
Arg 39 A Side Chain
Asn 115 A Side Chain
Lys 147 A Side Chain
Ser 171 A Side Chain
Asn 173 A Side Chain
Phe 175 A Side Chain
Asp 176 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 502 x

Metal Cofactors

No Associated Metal Cofactors

Reaction occurs across 8 steps

0.3333

Reaction occurs across 3 steps

Step 1
GIF of Reaction Step M0181.stg01

Lys53 attacks the carbonyl carbon of the phosphonoacetaldehyde aldehyde in a nucleophilic addition.
0 Step 1
GIF of Reaction Step M0036.stg01

Asp8 initiates a nucleophilic attack upon the chlorinated carbon of the substrate in a substitution reaction, eliminating chloride.
Step 2
GIF of Reaction Step M0181.stg02

The oxyanion deprotonates the covalently attached Lys53.
0.2 Step 2
GIF of Reaction Step M0036.stg02

Asp176 deprotonates water, which initiates a nucleophilic attack on the carbon covalently attached to Asp8 in a substitution reaction, eliminating Asp8.
Step 3
GIF of Reaction Step M0181.stg03

Lys53 initiates an elimination that results in the loss of the alcohol group, which deprotonates a water which in turn deprotonates His56.
0.42 Step 3
GIF of Reaction Step M0036.stg03

In an inferred return step, water deprotonates Asp176.
Step 4
GIF of Reaction Step M0181.stg04

Asp12 attacks the phosphate of the covalently bound intermediate in a nucleophilic substitution that cleaved the C-P bond and results in a phosphorylated Asp12 and alkylated Lys53
N/A Step 4
No Step with this number present
Step 5
GIF of Reaction Step M0181.stg05

Lys53 initiates a double bond rearrangement that causes the reduction of the C=C in the alkylated intermediate and deprotonates water. The activated water attacks the phosphate in a nucleophilic substitution that releases Asp12 and the phosphate product.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0181.stg06

His56 deprotonates water, which deprotonates a second water, which attacks the carbon of the C=N bond in a nucleophilic addition.
N/A Step 6
No Step with this number present
Step 7
GIF of Reaction Step M0181.stg07

Lys53 deprotonates the newly formed alcohol group.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0181.stg08

The oxyanion initiates an elimination that releases the acetaldehyde product and regenerates the active site Lys53.
N/A Step 8
No Step with this number present

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