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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 M0187 and M0269

These two reactions have a combined similarity of 0.49


M0187

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Comparison

M0269

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EC 5.1.2.2
mandelate racemase
Sub-Class EC 5.5.1.1
muconate cycloisomerase

Image of (S)-mandelate

right arrow

Image of (R)-mandelate

(S)-mandelate
C01984
CHEBI:17756
(R)-mandelate
C01983
CHEBI:32382
0

Image of cis,cis-hexadienedioate (cis,cis-muconate)

Image of proton

right arrow

Image of 2,5-dihydro-5-oxofuran-2-acetate

cis,cis-hexadienedioate (cis,cis-muconate)
C02480
CHEBI:32379
proton
C00080
CHEBI:24636
2,5-dihydro-5-oxofuran-2-acetate
C04105
CHEBI:58372

Catalytic CATH Codes

3.20.20.120

Catalytic CATH Codes

3.20.20.120

Active Site



0.64278

Active Site



Catalytic Residues

Type Number Chain Location of Function
Lys 164 A Side Chain
Lys 166 A Side Chain
Asp 270 A Side Chain
His 297 A Side Chain
Glu 317 A Side Chain
0.7142

Catalytic Residues

Type Number Chain Location of Function
Lys 167 A Side Chain
Lys 169 A Side Chain
Glu 327 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 360 x

Metal Cofactors

Type Het group Number Chain
manganese MN 374 A

Reaction occurs across 3 steps

0.52

Reaction occurs across 3 steps

Step 1
GIF of Reaction Step M0187.stg01

Lys166 deprotonates the (S)-mandelate substrate, which results in a keto-enol tautomerisation.
0.25 Step 1
GIF of Reaction Step M0269.stg01

The C1 carboxylate initiates a nucleophilic attack on the C4 double bond, initiating double bond rearrangement and forming the enol intermediate.
Step 2
GIF of Reaction Step M0187.stg02

The intermediate undergoes another keto-enol tautomerisation which reprotonates the intermediate from His297.
0.66 Step 2
GIF of Reaction Step M0269.stg02

Glu327 deprotonates the enol resulting in the protonation of C5, supplied by Lys169, to produce the cyclic non-planar product.
Step 3
GIF of Reaction Step M0187.stg03

His297 deprotonates water, which deprotonates Lys166 in an inferred return step.
0.5 Step 3
GIF of Reaction Step M0269.stg03

In an inferred return step, Lys169 deprotonates water to regenerate the active site.

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