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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 M0116 and M0220

These two reactions have a combined similarity of 0.20


M0116

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Comparison

M0220

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EC 1.6.1.2
NAD(P)+ transhydrogenase (AB-specific)
Class EC 4.1.1.7
benzoylformate decarboxylase

Image of NADP

Image of NADH

right arrow

Image of NADPH

Image of NAD

NADP
C00006
CHEBI:18009
NADH
C00004
CHEBI:16908
NADPH
C00005
CHEBI:16474
NAD
C00003
CHEBI:15846
0.06

Image of alpha-Oxo-benzeneacetic acid

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Image of Carbon dioxide

Image of Benzaldehyde

alpha-Oxo-benzeneacetic acid
C02137
CHEBI:18280
Carbon dioxide
C00011
CHEBI:16526
Benzaldehyde
C00261
CHEBI:17169

Catalytic CATH Codes

3.40.50.720
3.40.50.1770
3.40.50.1220

Catalytic CATH Codes

3.40.50.1220
3.40.50.970

Active Site



0

Active Site



Catalytic Residues

Type Number Chain Location of Function
Arg 127 A Side Chain
Asp 135 A Side Chain
Tyr 235 A Side Chain
Asp 132 C Side Chain
0

Catalytic Residues

Type Number Chain Location of Function
Glu 47 B Side Chain
Glu 28 B Side Chain
His 70 B Side Chain
Ser 26 B Side Chain
Gly 401 A Main Chain Carbonyl
His 281 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

Type Identity Chain
Thiamine diphosphate TDP 533 A

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 529 A

Reaction occurs across 3 steps

0.3055

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0116.stg01

Asp132C obtains a proton, causing a rearrangement of the active site.
0.12 Step 1
GIF of Reaction Step M0220.stg01

Glu47B deprotonates the thiamine diphosphate cofactor, which initiates double bond rearrangement that results in the deprotonation of the N=CH-S group, activating the cofactor.
Step 2
GIF of Reaction Step M0116.stg02

NAD eliminates a hydride ion, which adds to NADP.
0 Step 2
GIF of Reaction Step M0220.stg02

The carbanion of thiamine diphosphate attacks the carbonyl carbon of alpha-oxo-benzeneacetic acid in a nucleophilic addition. The formed oxyanion deprotonates His70B
Step 3
GIF of Reaction Step M0116.stg03

Asp132C releases its proton.
0 Step 3
GIF of Reaction Step M0220.stg03

Carbon dioxide eliminates from the covalently attached aromatic intermediate. Thiamine diphosphate acts as an electron sink.
Step 4
No Step with this number present
N/A Step 4
GIF of Reaction Step M0220.stg04

Thiamine diphosphate initiates a double bond rearrangement, which results in the intermediate being protonated by His281A.
Step 5
No Step with this number present
N/A Step 5
GIF of Reaction Step M0220.stg05

His70B deprotonates the hydroxide of the intermediate, which initiates an elimination which results in a reformation of the carbanionic activated cofactor and the benzaldehyde product.
Step 6
No Step with this number present
N/A Step 6
GIF of Reaction Step M0220.stg06

The carbanion of the thiamine diphosphate cofactor deprotonates the adjacent amine, which initiates double bond rearrangement that results in the deprotonation of Glu47B. His281A deprotonates water.

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