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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 M0201 and M0024

These two reactions have a combined similarity of 0.27


M0201

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Comparison

M0024

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EC 6.4.1.3
propionyl-CoA carboxylase
Class EC 3.8.1.7
4-chlorobenzoyl-CoA dehalogenase

Image of ATP

Image of bicarbonate

Image of propanoyl-CoA

right arrow

Image of proton

Image of (S)-2-methyl-3-oxopropanoyl-CoA

Image of phosphate

Image of ADP

ATP
C00002
CHEBI:30616
bicarbonate
C00288
CHEBI:17544
propanoyl-CoA
C00100
CHEBI:57392
proton
C00080
CHEBI:24636
(S)-2-methyl-3-oxopropanoyl-CoA
C00683
CHEBI:57326
phosphate
C00009
CHEBI:18367
ADP
C00008
CHEBI:456216
0.09

Image of water

Image of 4-chlorobenzoyl-coenzyme A

right arrow

Image of proton

Image of chloride ion

Image of 4-hydroxybenzoyl-coenzyme A

water
C00001
CHEBI:15377
4-chlorobenzoyl-coenzyme A
C06387
CHEBI:15498
proton
C00080
CHEBI:24636
chloride ion
C00698
CHEBI:17996
4-hydroxybenzoyl-coenzyme A
C02949
CHEBI:15500

Catalytic CATH Codes

3.90.226.10

Catalytic CATH Codes

3.90.226.10

Active Site



0.29997

Active Site



Catalytic Residues

Type Number Chain Location of Function
Gly 182 A Main Chain Amide
Gly 183 A Main Chain Amide
Gly 419 B Main Chain Amide
Ala 420 B Main Chain Amide
0.3333

Catalytic Residues

Type Number Chain Location of Function
Phe 64 A Main Chain Amide
Ala 86 A Main Chain Carbonyl
His 90 A Side Chain
Gly 114 A Main Chain Amide
Trp 137 A Side Chain
Asp 145 A Side Chain

Organic Cofactors

Type Identity Chain
Biotin BTN 5600

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG(not in PDB) 1 x

Metal Cofactors

No Associated Metal Cofactors

Reaction occurs across 7 steps

0.2967

Reaction occurs across 4 steps

Step 1
GIF of Reaction Step M0201.stg01

Reaction occurs in the alpha-subunit. The bicarbonate is deprotonated by an unidentified base. The activate bicarbonate then acts as a nucleophile and attacks the gamma-phosphate in a substitution reaction, liberating ADP. Mg(II) stabilises/activates the ATP
0.13 Step 1
GIF of Reaction Step M0024.stg01

His90 deprotonates Asp145, which initiates a nucleophilic attack on the C4 of the 4-chlorobenzoyl-coenzyme A in an addition reaction. The conjugated double bonds rearrange to form an oxyanion, which is stabilised by the main chain amides of Phe64 and Gly114.
Step 2
GIF of Reaction Step M0201.stg02

Reaction occurs in the alpha-subunit. The phosphorylated bicarbonate undergoes a decarboxylation reaction (E1cb) to liberate carbon dioxide and phosphate.
0.08 Step 2
GIF of Reaction Step M0024.stg02

The oxyanion collapses with rearrangement of the conjugated double bonds, eliminating chlorine, which deprotonates the His90.
Step 3
GIF of Reaction Step M0201.stg03

Reaction occurs in the alpha-subunit. The phosphate deprotonates one of the N-H groups of biotin with concomitant tautomerisation to produce an oxyanion.
0.14 Step 3
GIF of Reaction Step M0024.stg03

His90 deprotonates water, which initiates a nucleophilic attack on the carboxylic carbon of the covalently attached Asp145, forming a new oxyanion, which is stabilised by Try137.
Step 4
GIF of Reaction Step M0201.stg04

Reaction occurs in the alpha-subunit. The oxyanion re-forms the carbonyl group, causing the C=N bond of the activated biotin to add to the carbon dioxide in a nucleophilic manner.
0.14 Step 4
GIF of Reaction Step M0024.stg04

The oxyanion collapses, eliminating Asp145 as an electrofuge. The newly formed phenolic oxygen deprotonates His90.
Step 5
GIF of Reaction Step M0201.stg05

Reaction occurs in the beta-subunit. Once the carboxylated biotin has relocated to the beta-subunit, the biotin undergoes a decarboxylation reaction (E1cb) to liberate carbon dioxide and the activated biotin molecule. the main chain amides of Gly419B and Ala420B stabilise the oxyanion of the activated biotin.
N/A Step 5
No Step with this number present
Step 6
GIF of Reaction Step M0201.stg06

Reaction occurs in the beta-subunit. The oxyanion re-forms the carbonyl group, causing the C=N bond of the activated biotin to deprotonate the propanoyl-CoA with concomitant tautomerisation. The main chain amides of Gly182 and Gly183 stabilise the activated propanoyl-CoA, the main chain amides of Gly419B and Ala420B stabilise the oxyanion of the activated biotin.
N/A Step 6
No Step with this number present
Step 7
GIF of Reaction Step M0201.stg07

Reaction occurs in the beta-subunit. The oxyanion re-forms the carbonyl group causing the C=C bond of the activated propanoyl-CoA to add to the carbon dioxide molecule in an electrophilic manner.
N/A Step 7
No Step with this number present

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