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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 M0218 and M0248

These two reactions have a combined similarity of 0.72


M0218

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Comparison

M0248

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EC 3.1.1.3
triacylglycerol lipase
Class EC 1.11.1.10
chloride peroxidase

Image of Triacylglycerol

Image of Water

right arrow

Image of Carboxylate

Image of Diacylglycerol

Triacylglycerol
C00422
CHEBI:17855
Water
C00001
CHEBI:15377
Carboxylate
C00060
CHEBI:18245
Diacylglycerol
C00165
CHEBI:17815
0.22

Image of chloride ion

Image of hydrogen peroxide

Image of proton

Image of alkane

right arrow

Image of water

Image of chlorinated alkane

chloride ion
C00698
CHEBI:17996
hydrogen peroxide
C00027
CHEBI:16240
proton
C00080
CHEBI:24636
alkane
C01371
CHEBI:18310
2 water
C00001
CHEBI:15377
chlorinated alkane
C01334
CHEBI:23128

Catalytic CATH Codes

3.40.50.1820

Catalytic CATH Codes

3.40.50.1820

Active Site



0.63814

Active Site



Catalytic Residues

Type Number Chain Location of Function
Ser 152 A Side Chain
His 263 A Side Chain
Asp 176 A Side Chain
Phe 77 A Main Chain Amide
Leu 153 A Main Chain Amide
0.6666

Catalytic Residues

Type Number Chain Location of Function
Asp 228 A Side Chain
His 257 A Side Chain
Ser 98 A Side Chain
Met 99 A Main Chain Amide
Phe 32 A Main Chain Amide

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

No Associated Metal Cofactors

Reaction occurs across 4 steps

0.8378

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0218.stg01

His263 (part of a Ser-His-Asp triad) deprotonates Ser152, which attacks the carboxy carbon of the triacylglycerol substrate in a nucleophilic addition.
1 Step 1
GIF of Reaction Step M0248.stg01

His257 deprotonates Ser98, which initiates a nucleophilic attack upon the carboxylate carbon of the carboxylic acid cofactor.
Step 2
GIF of Reaction Step M0218.stg02

The oxyanion collapses, initiating an elimination of the diacylglycerol product, which deprotonates His263 and acylated Ser152.
1 Step 2
GIF of Reaction Step M0248.stg02

The oxyanion collapses, eliminating a water molecule with concomitant deprotonation of His257.
Step 3
GIF of Reaction Step M0218.stg03

His263 deprotonates water, which attacks the carboxyl carbon of the acylated Ser152 in a nucleophilic addition.
1 Step 3
GIF of Reaction Step M0248.stg03

His257 deprotonates the hydrogen peroxide substrate, initiating a nucleophilic attack on the carbonyl carbon of the intermediate in an addition reaction.
Step 4
GIF of Reaction Step M0218.stg04

The oxyanion collapses, initiating an elimination of the carboxylate product, and Ser152, which deprotonates His263.
1 Step 4
GIF of Reaction Step M0248.stg04

The oxyanion collapses, eliminating the Ser98 with concomitant deprotonation of His257.
Step 5
No Step with this number present
N/A Step 5
GIF of Reaction Step M0248.stg05

A chloride ion initiates a nucleophilic attack upon the peroxo-intermediate in a substitution reaction, regenerating the carboxylic acid cofactor and producing the hypochlorous acid intermediate.
Step 6
No Step with this number present
N/A Step 6
GIF of Reaction Step M0248.stg06

The hypochlorous acid halogenates the alkane.

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