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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 M0026 and M0242

These two reactions have a combined similarity of 0.51


M0026

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Comparison

M0242

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EC 4.6.1.13
phosphatidylinositol diacylglycerol-lyase
Class EC 3.1.4.41
sphingomyelin phosphodiesterase D

Image of 1-phosphatidyl-1D-myo-inositol

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Image of 1,2-diacylglycerol

Image of D-myo-inositol 1,2-cyclic phosphate

1-phosphatidyl-1D-myo-inositol
C01194
CHEBI:57880
1,2-diacylglycerol
C00641
CHEBI:17815
D-myo-inositol 1,2-cyclic phosphate
C04299
CHEBI:18426
1

Image of water

Image of Sphingomyelin

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Image of Ceramide 1-phosphate

Image of Choline

water
C00001
CHEBI:15377
Sphingomyelin
C00550
CHEBI:58216
Ceramide 1-phosphate
C02960
Choline
C00114
CHEBI:15354

Catalytic CATH Codes

3.20.20.190

Catalytic CATH Codes

3.20.20.190

Active Site



0.5625

Active Site



Catalytic Residues

Type Number Chain Location of Function
His 32 A Side Chain
Asp 33 A Side Chain
Arg 69 A Side Chain
His 82 A Side Chain
Asp 274 A Side Chain
0.625

Catalytic Residues

Type Number Chain Location of Function
His 47 A Side Chain
His 12 A Side Chain
Gly 48 A Main Chain Carbonyl
Asp 34 A Side Chain
Asn 252 A Side Chain
Asp 233 A Side Chain
Asp 52 A Side Chain
Trp 230 A Side Chain
Lys 93 A Side Chain

Organic Cofactors

No Associated Organic Cofactors

Organic Cofactors

No Associated Organic Cofactors

Metal Cofactors

No Associated Metal Cofactors

Metal Cofactors

Type Het group Number Chain
magnesium MG 601 _

Reaction occurs across 2 steps

0.4285

Reaction occurs across 4 steps

Step 1
GIF of Reaction Step M0026.stg01

His32 deprotonates the hydroxy group adjacent to the phosphate, which initiates an intramolecular nucleophilic addition of the oxyanion to the phosphate, which proceeds through a pentavalent transition state, to eliminate the product alcohol in a substitution reaction, with concomitant deprotonation of His82.
0 Step 1
GIF of Reaction Step M0242.stg01

His47 is the nucleophile for attack on the phosphorous of the scissile phosphodiester. A penta-coordinated intermediate is formed.
Step 2
GIF of Reaction Step M0026.stg02

His82 deprotonates water, which in turn deprotonates His32 in an inferred step.
0.4 Step 2
GIF of Reaction Step M0242.stg02

The intermediate collapses and eliminates choline, which is protonated by His12.
Step 3
No Step with this number present
N/A Step 3
GIF of Reaction Step M0242.stg03

His12 deprotonates water, which then acts as the nucleophile for attack on the phosphorous centre of the intermediate. A penta-coordinated intermediate is formed.
Step 4
No Step with this number present
N/A Step 4
GIF of Reaction Step M0242.stg04

The intermediate collapses and eliminates His47. This forms ceramide 1-phosphate.

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