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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 M0264 and M0253

These two reactions have a combined similarity of 0.29


M0264

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Comparison

M0253

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EC 2.5.1.21
squalene synthase
Serial Number EC 2.5.1.10
geranyltranstransferase

Image of NADPH

Image of 2-trans,6-trans-farnesyl diphosphate

right arrow

Image of proton

Image of NADP

Image of squalene

Image of diphosphate

NADPH
C00005
CHEBI:16908
2 2-trans,6-trans-farnesyl diphosphate
C00448
CHEBI:175763
proton
C00080
CHEBI:24636
NADP
C00006
CHEBI:15846
squalene
C00751
CHEBI:15440
2 diphosphate
C00013
CHEBI:33019
0.77

Image of isopentenyl diphosphate

Image of geranyl diphosphate

right arrow

Image of trans,trans-farnesyl diphosphate

Image of diphosphate

isopentenyl diphosphate
C00129
CHEBI:128769
geranyl diphosphate
C00341
CHEBI:58057
trans,trans-farnesyl diphosphate
C00448
CHEBI:17407
diphosphate
C00013
CHEBI:33019

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.12852

Active Site



Catalytic Residues

Type Number Chain Location of Function
Tyr 171 A Side Chain
Arg 228 A Side Chain
Arg 218 A Side Chain
Phe 288 A Side Chain
0.1428

Catalytic Residues

Type Number Chain Location of Function
Phe 112 A Side Chain
Lys 214 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium No Available PDB Information
magnesium No Available PDB Information
magnesium No Available PDB Information

Metal Cofactors

Type Het group Number Chain
magnesium MG 402 A
magnesium MG 403 A
magnesium No Available PDB Information

Reaction occurs across 7 steps

0.2916

Reaction occurs across 3 steps

Step 1
GIF of Reaction Step M0264.stg01

Pyrophosphate is eliminated with concomitant deprotonation of Tyr171.
0.2 Step 1
GIF of Reaction Step M0253.stg01

The substrate undergoes heterolysis. The diphosphate product remains associated with the active site, and the cabocation is delocalised over the three terminal carbon atoms of the intermediate.
Step 2
GIF of Reaction Step M0264.stg02

The second molecule of farnesyl diphosphate initiates an electrophilic attack on the intermediate formed.
0.6 Step 2
GIF of Reaction Step M0253.stg02

The double bond of isopentenyl diphosphate adds to the terminal carbocation in an electrophilic addition.
Step 3
GIF of Reaction Step M0264.stg03

Tyr171 acts as a base to deprotonate the intermediate, forming the stable intermediate presqualene diphosphate, the product of the first half reaction.
0.5 Step 3
GIF of Reaction Step M0253.stg03

The diphosphate formed in the initial heterolysis deprotonates the carbon adjacent to the newly formed carbocation, forming a new double bond in the trans,trans-farnesyl diphosphate product.
Step 4
GIF of Reaction Step M0264.stg04

The substrate undergoes heterolysis.
N/A Step 4
No Step with this number present
Step 5
GIF of Reaction Step M0264.stg05

A 1,2 sigmatropic rearrangement to produce the cyclobutyl intermediate.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0264.stg06

A 1,2 sigmatropic rearrangement to produce the second cyclopropyl intermediate.
N/A Step 6
No Step with this number present
Step 7
GIF of Reaction Step M0264.stg07

A hydride transfer from NADP caused the cleavage of the cyclopropyl group to produce squalene.
N/A Step 7
No Step with this number present

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