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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 M0092 and M0090

These two reactions have a combined similarity of 0.54


M0092

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Comparison

M0090

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EC 1.1.1.22
UDP-glucose 6-dehydrogenase
Class EC 3.3.1.1
adenosylhomocysteinase

Image of UDP-glucose

Image of water

Image of NAD

right arrow

Image of proton

Image of NADH

Image of UDP-glucuronate

UDP-glucose
C00029
CHEBI:58367
water
C00001
CHEBI:15377
2 NAD
C00003
CHEBI:18009
2 proton
C00080
CHEBI:24636
2 NADH
C00004
CHEBI:16908
UDP-glucuronate
C00167
CHEBI:17200
0.11

Image of S-adenosyl-L-homocysteine

Image of water

right arrow

Image of adenosine

Image of L-homocysteine

S-adenosyl-L-homocysteine
C00021
CHEBI:57856
water
C00001
CHEBI:15377
adenosine
C00212
CHEBI:16335
L-homocysteine
C00155
CHEBI:58199

Catalytic CATH Codes

3.40.50.720
1.10.1040.10

Catalytic CATH Codes

3.40.50.1480
3.40.50.720

Active Site



0.35754

Active Site



Catalytic Residues

Type Number Chain Location of Function
Thr 118 A Side Chain
Glu 145 A Side Chain
Lys 204 A Side Chain
Asn 208 A Side Chain
Cys 260 A Side Chain
Asp 264 A Side Chain
0.3846

Catalytic Residues

Type Number Chain Location of Function
His 54 A Side Chain
Asp 130 A Side Chain
Lys 185 A Side Chain
Asp 189 A Side Chain
Asn 190 A Side Chain
Cys 194 A Side Chain
His 300 A Side Chain
Ser 360 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

Type Identity Chain
NAD NAD 432 A

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

No Associated Metal Cofactors

Reaction occurs across 6 steps

0.6883

Reaction occurs across 7 steps

Step 1
GIF of Reaction Step M0092.stg01

Asp264 deprotonates water, which deprotonated Lys204 which deprotonates the CH3OH group of UDP, which causes the elimination of a hydride which adds to NAD
0.85 Step 1
GIF of Reaction Step M0090.stg01

Asp189 deprotonates Lys185, which in turn deprotonates 3'-OH of the substrate. This cause the elimination of a hydride ion, which is transferred to the NAD cofactor.
Step 2
GIF of Reaction Step M0092.stg02

Cys260 initiates a nucleophilic attack on the formed carbonyl carbon in an addition reaction.
0 Step 2
GIF of Reaction Step M0090.stg02

Asp130 deprotonates the 4'-CH of the substrate, forming a carbanion.
Step 3
GIF of Reaction Step M0092.stg03

The oxyanion collapses, eliminating a second hydride, which adds to a second molecule of NAD.
0.14 Step 3
GIF of Reaction Step M0090.stg03

The 4'-carbanion initiates the elimination of the homocysteine thiolate.
Step 4
GIF of Reaction Step M0092.stg04

Glu145 deprotonates water, which initiates a nucleophilic attack on the carbonyl carbon of the covalently bound substrate.
0.33 Step 4
GIF of Reaction Step M0090.stg04

His54 deprotonates water, which initiates a nucleophilic attack upon the C=C in an addition reaction, re-forming the carbanion.
Step 5
GIF of Reaction Step M0092.stg05

The oxyanion collapses, eliminating Cys260.
0 Step 5
GIF of Reaction Step M0090.stg05

The homocysteine thiolate deprotonates His54 in an inferred step.
Step 6
GIF of Reaction Step M0092.stg06

In an inferred return step, two water molecules deprotonate Glu145 and Asp264.
0.25 Step 6
GIF of Reaction Step M0090.stg06

The carbanion deprotonates Asp130.
Step 7
No Step with this number present
N/A Step 7
GIF of Reaction Step M0090.stg07

The NAD cofactor eliminates the hydride ion, which adds to the 3'-C initiating the oxyanion to deprotonate Lys185, which in turn deprotonates Asp189.

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