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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 M0253 and M0261

These two reactions have a combined similarity of 0.36


M0253

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Comparison

M0261

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EC 2.5.1.10
geranyltranstransferase
Class EC 4.2.3.9
aristolochene synthase

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
0.38

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

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.4608

Active Site



Catalytic Residues

Type Number Chain Location of Function
Phe 112 A Side Chain
Lys 214 A Side Chain
0.5

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

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

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

Metal Cofactors

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

Reaction occurs across 3 steps

0.3333

Reaction occurs across 5 steps

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.
0.33 Step 1
GIF of Reaction Step M0261.stg01

The C10-C11 double bond initiates an electrophilic substitution at the C1, eliminating the diphosphate product.
Step 2
GIF of Reaction Step M0253.stg02

The double bond of isopentenyl diphosphate adds to the terminal carbocation in an electrophilic addition.
0 Step 2
GIF of Reaction Step M0261.stg02

Lys206 deprotonates the C12, producing the neutral Germacrene A intermediate.
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.
0 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.
Step 4
No Step with this number present
N/A 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.
Step 5
No Step with this number present
N/A Step 5
GIF of Reaction Step M0261.stg05

Bulk solvent deprotonates Lys206 in an inferred return step.

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