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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 M0261 and M0264

These two reactions have a combined similarity of 0.47


M0261

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Comparison

M0264

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EC 4.2.3.9
aristolochene synthase
Class EC 2.5.1.21
squalene synthase

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

right arrow

Image of aristolochene

Image of diphosphate

2-trans,6-trans-farnesyl diphosphate
C00448
CHEBI:175763
aristolochene
C02004
CHEBI:43445
diphosphate
C00013
CHEBI:33019
0.38

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

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.2839

Active Site



Catalytic Residues

Type Number Chain Location of Function
Tyr 92 A Side Chain
Phe 112 A Side Chain
Phe 178 A Side Chain
Lys 206 A Side Chain
Trp 333 A Side Chain
0.3

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

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium none1 0 none
magnesium none2 0 none
magnesium none3 0 none

Metal Cofactors

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

Reaction occurs across 5 steps

0.5666

Reaction occurs across 7 steps

Step 1
GIF of Reaction Step M0261.stg01

The C10-C11 double bond initiates an electrophilic substitution at the C1, eliminating the diphosphate product.
0.33 Step 1
GIF of Reaction Step M0264.stg01

Pyrophosphate is eliminated with concomitant deprotonation of Tyr171.
Step 2
GIF of Reaction Step M0261.stg02

Lys206 deprotonates the C12, producing the neutral Germacrene A intermediate.
0.12 Step 2
GIF of Reaction Step M0264.stg02

The second molecule of farnesyl diphosphate initiates an electrophilic attack on the intermediate formed.
Step 3
GIF of Reaction Step M0261.stg03

The C2-C3 double bond initiates an electrophilic attack on the C7, which causes the protonation of C6 from Lys206 to form the Eudesmane cation intermediate.
0.11 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.
Step 4
GIF of Reaction Step M0261.stg04

Lys206 deprotonates the C8 carbon, which forms a double bond between C8 and C7. This initiates the migration of the C14 methyl from C7 to C8 and a migration of a hydride from C2 to C3 to form the Aristolochene product.
0 Step 4
GIF of Reaction Step M0264.stg04

The substrate undergoes heterolysis.
Step 5
GIF of Reaction Step M0261.stg05

Bulk solvent deprotonates Lys206 in an inferred return step.
0 Step 5
GIF of Reaction Step M0264.stg05

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

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

A hydride transfer from NADP caused the cleavage of the cyclopropyl group to produce squalene.

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