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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 M0259

These two reactions have a combined similarity of 0.33


M0261

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Comparison

M0259

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EC 4.2.3.9
aristolochene synthase
Class EC 5.5.1.8
bornyl diphosphate 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 geranyl diphosphate

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Image of (+)-bornyl diphosphate

geranyl diphosphate
C00341
CHEBI:58057
(+)-bornyl diphosphate
C03190
CHEBI:57293

Catalytic CATH Codes

1.10.600.10

Catalytic CATH Codes

1.10.600.10

Active Site



0.3375

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
0.375

Catalytic Residues

Type Number Chain Location of Function
Trp 323 A Side Chain
Phe 578 A Side Chain
Ile 344 A Side Chain
Val 452 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 MG 701 A
magnesium MG 702 A
magnesium MG 703 A

Reaction occurs across 5 steps

0.3333

Reaction occurs across 6 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 M0259.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 M0261.stg02

Lys206 deprotonates the C12, producing the neutral Germacrene A intermediate.
0.2 Step 2
GIF of Reaction Step M0259.stg02

The diphosphate initiates nucleophilic attack at the C4 carbon, which causes double bond rearrangement and the formation of the linalyl diphosphate intermediate.
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 Step 3
GIF of Reaction Step M0259.stg03

The linalyl diphosphate 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 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.
0.15 Step 4
GIF of Reaction Step M0259.stg04

The terminal double bond adds to the newly formed carbocation in an intramolecular electrophilic addition resulting in a cyclic intermediate.
Step 5
GIF of Reaction Step M0261.stg05

Bulk solvent deprotonates Lys206 in an inferred return step.
0 Step 5
GIF of Reaction Step M0259.stg05

The remaining double bond adds to the newly formed carbocation in an intramolecular electrophilic addition resulting in a bicyclic intermediate.
Step 6
No Step with this number present
N/A Step 6
GIF of Reaction Step M0259.stg06

The diphosphate initiates nucleophilic attack at the carbocation, forming the final product.

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