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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 M0259 and M0253

These two reactions have a combined similarity of 0.30


M0259

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Comparison

M0253

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EC 5.5.1.8
bornyl diphosphate synthase
Class EC 2.5.1.10
geranyltranstransferase

Image of geranyl diphosphate

right arrow

Image of (+)-bornyl diphosphate

geranyl diphosphate
C00341
CHEBI:58057
(+)-bornyl diphosphate
C03190
CHEBI:57293
0.45

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



0.18

Active Site



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
0.2

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 MG 701 A
magnesium MG 702 A
magnesium MG 703 A

Metal Cofactors

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

Reaction occurs across 6 steps

0.3333

Reaction occurs across 3 steps

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.
1 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 M0259.stg02

The diphosphate initiates nucleophilic attack at the C4 carbon, which causes double bond rearrangement and the formation of the linalyl diphosphate intermediate.
0.25 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 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.
0 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 M0259.stg04

The terminal double bond adds to the newly formed carbocation in an intramolecular electrophilic addition resulting in a cyclic intermediate.
N/A Step 4
No Step with this number present
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.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0259.stg06

The diphosphate initiates nucleophilic attack at the carbocation, forming the final product.
N/A Step 6
No Step with this number present

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