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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 M0265 and M0259

These two reactions have a combined similarity of 0.20


M0265

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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 5-epi-aristolochene

Image of diphosphate

2-trans,6-trans-farnesyl diphosphate
C00448
CHEBI:175763
5-epi-aristolochene
X00127
CHEBI:23925
diphosphate
C00013
CHEBI:33019
0.39

Image of geranyl diphosphate

right arrow

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



0.0629

Active Site



Catalytic Residues

Type Number Chain Location of Function
Arg 264 A Side Chain
Arg 441 A Side Chain
Thr 401 A Main Chain Carbonyl
Thr 402 A Main Chain Carbonyl
Thr 403 A Side Chain
Tyr 527 A Side Chain
Asp 525 A Side Chain
Tyr 520 A Side Chain
Asp 444 A Side Chain
Trp 273 A Side Chain
0.04

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 MG 851 A
magnesium MG 852 A
magnesium MG 853 A

Metal Cofactors

Type Het group Number Chain
magnesium MG 701 A
magnesium MG 702 A
magnesium MG 703 A

Reaction occurs across 9 steps

0.2359

Reaction occurs across 6 steps

Step 1
GIF of Reaction Step M0265.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.
1 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 M0265.stg02

The C10-C11 double bond initiates an electrophilic attack on the positive carbocation, forming the first cyclic intermediate.
0.25 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 M0265.stg03

Asp525 deprotonates the intermediate to produce germacrene.
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 M0265.stg04

Asp444 in the Asp444-Tyr520-Asp525 triad deprotonated Tyr520, which in turn deprotonates Asp525.
0 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 M0265.stg05

The C2-C3 double bond initiates an electrophilic addition to the C6 double bond, which deprotonates Tyr520, in turn deprotonating Asp444.
0.3 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
GIF of Reaction Step M0265.stg06

The C2 hydride migrates to the C3.
0 Step 6
GIF of Reaction Step M0259.stg06

The diphosphate initiates nucleophilic attack at the carbocation, forming the final product.
Step 7
GIF of Reaction Step M0265.stg07

The C14 methyl migrates to the planar C2 carbocation.
N/A Step 7
No Step with this number present
Step 8
GIF of Reaction Step M0265.stg08

Trp273 deprotonates the reactive intermediate, producing the final product.
N/A Step 8
No Step with this number present
Step 9
GIF of Reaction Step M0265.stg09

Trp273 is deprotonated in order to renegerate the active state of the enzyme.
N/A Step 9
No Step with this number present

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