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Information on EC 3.1.1.4 - phospholipase A2 and Organism(s) Naja naja and UniProt Accession P15445

for references in articles please use BRENDA:EC3.1.1.4

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3.1 Acting on ester bonds

3.1.1 Carboxylic-ester hydrolases

3.1.1.4 phospholipase A2

Also acts on phosphatidylethanolamine, choline plasmalogen and phosphatides, removing the fatty acid attached to the 2-position. Requires Ca2+.

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Naja naja

UNIPROT: P15445

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Word Map

The taxonomic range for the selected organisms is: Naja naja
The enzyme appears in selected viruses and cellular organisms

Reaction Schemes

phosphatidylcholine

+

=

1-acylglycerophosphocholine

+

+

=

+

Synonyms

phospholipase a2, cpla2, spla2, spla(2), prdx6, cytosolic phospholipase a2, crotoxin, pla2s, ipla2, spla2-iia, show all synonyms

show all synonyms

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Go to Synonym Search

PLA2

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secretory phospholipase A2

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14 kDa phospholipase A2

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Agkistrotoxin

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amdI1

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Ammodytin I2

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APLA

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APP-D-49

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ASPLA1

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ASPLA10

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ASPLA11

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ASPLA12

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ASPLA13

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ASPLA14

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ASPLA15

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ASPLA16

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ASPLA17

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ASPLA2

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ASPLA3

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ASPLA4

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ASPLA5

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ASPLA6

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ASPLA7

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ASPLA8

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ASPLA9

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ATX

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Basic protein I/II

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BJ-PLA2

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BJUPLA2

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BPI/BPII

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Ca2+-independent iPLA2

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CaI-PLA2

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Caudoxin

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cPm09

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cytosolic cPLA2

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Enhancing factor

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GIA cobra venom PLA2

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GIIC sPLA2

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GIID sPLA2

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GIIE sPLA2

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GIIF sPLA2

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GIII sPLA2

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group IA PLA2

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Group IB phospholipase A2

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Group IIA phospholipase A2

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Group V phospholipase A2

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Group VI phospholipase A2

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GVI PLA2

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GX sPLA2

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GXII sPLA2

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GXIII sPLA2

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iPLA2

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lecithinase A

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MP-III 4R

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Muscarinic inhibitor

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Myotoxin

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NAJPLA-2A

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NAJPLA-2B

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NAJPLA-2C

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Nigexine

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NN-X-PLA2

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NN-XI-PLA2

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NN-XIa-PLA2

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NND-IV-PLA2

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Non-pancreatic secretory phospholipase A2

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Notechis 11'2

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Notexin

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NPLA

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NPS-PLA2

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OHV A-PLA2

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OHV-APLA2

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pgPLA 1a/pgPLA 2a

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phosphatidase

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phosphatide 2-acylhydrolase

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phosphatidolipase

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Phosphatidylcholine 2-acylhydrolase

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Phosphatidylcholine 2-acylhydrolase GIIC

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Phosphatidylcholine 2-acylhydrolase GIID

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Phosphatidylcholine 2-acylhydrolase GIIE

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Phosphatidylcholine 2-acylhydrolase GIIF

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Phosphatidylcholine 2-acylhydrolase GIII

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Phosphatidylcholine 2-acylhydrolase GX

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Phosphatidylcholine 2-acylhydrolase GXII

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Phosphatidylcholine 2-acylhydrolase GXIII

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phospholipase A

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phospholipase A2

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Phospholipase A2 inhibitor

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pkP5

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PLA2

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PLA2-10

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PLA2-VI

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PLA2-VII

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PLA2IID

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platelet activating factor acetyl hydrolase

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Pt-PLA1

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Pt-PLA2

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secreted sPLA2

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secretory phospholipase A2

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Secretory-type PLA, stroma-associated homolog

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sPLA(2)-IID

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sPLA(2)-IIE

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sPLA(2)-IIF

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sPLA2

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TMV-K49

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Toxin VI

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Toxin VI:5

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Go to Reaction Type Search

hydrolysis of carboxylic ester

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Go to Pathway Search

BRENDA

lipid metabolism

KEGG

alpha-Linolenic acid metabolism, Arachidonic acid metabolism, Biosynthesis of secondary metabolites, Ether lipid metabolism, Glycerophospholipid metabolism, Linoleic acid metabolism

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-, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -

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Go to Systematic Name Search

phosphatidylcholine 2-acylhydrolase

Also acts on phosphatidylethanolamine, choline plasmalogen and phosphatides, removing the fatty acid attached to the 2-position. Requires Ca2+.

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Go to CAS Registry Number Search

9001-84-7

-

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Go to Substrate/Product Search

1,2-diacyl-sn-glycero-3-phosphorylcholine + H2O

1-acyl-sn-glycero-3-phosphorylcholine + fatty acid

show the reaction diagram

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?

1,2-dimyristol-sn-glycero-phosphomethanol lithium salt + H2O

myristic acid + 1-myristoyl-sn-glycerophosphomethanol

show the reaction diagram

-

-

-

?

1-palmitoyl-2-(12-(3-(4-hydroxyphenyl)propionyl)amino dodecanoyl)phosphatidylcholine + H2O

1-palmitoyl-sn-glycerophosphorylcholine + 12-(3-(4-hydroxyphenyl)propionyl)amino dodecanoate

show the reaction diagram

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-

-

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?

phosphatidylcholine + H2O

1-acylglycerophosphocholine + fatty acid

show the reaction diagram

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?

phosphatidylcholine + H2O

lysophosphatidylcholine + a fatty acid

show the reaction diagram

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?

phosphatidylethanolamine + H2O

1-acylglycerophosphorylethanolamine + fatty acid

show the reaction diagram

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?

phosphatidylserine + H2O

1-acylglycerophosphoserine + fatty acid

show the reaction diagram

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?

phospholipids + H2O

?

show the reaction diagram

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133893, 133903, 133906

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-

?

additional information

?

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show

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Go to Natural Substrate Search

phosphatidylcholine + H2O

lysophosphatidylcholine + a fatty acid

show the reaction diagram

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?

phospholipids + H2O

?

show the reaction diagram

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133893, 133903, 133906

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?

additional information

?

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show

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Go to Metals and Ions Search

Ca2+

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Ca2+

show

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Go to Inhibitor Search

minocycline

interferes with the conformation of the active-site Ca2+-binding loop, preventing Ca2+ binding, and shields the active site from substrate entrance, resulting in inhibition of the enzyme. Dissociation constant for PLA2 is Kd = 0.00018 M

1-hexadecyl-3-trifluoroethylglycero-sn-2-phosphomethanol

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MJ33, competitive inhibitor

3-[4'-(hydroxyimino-p-tolyl-methyl)-phenyl]-4-phenyl-sydnone

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in vivo edema inducing activity, overview

3-[4'-(hydroxyimino-p-tolyl-methyl)-phenyl]-sydnone

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in vivo edema inducing activity, overview

3-[4'-(hydroxyimino-phenyl-methyl)-phenyl]-4-phenyl-sydnone

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in vivo edema inducing activity, overview

3-[4'-(hydroxyimino-phenyl-methyl)-phenyl]-sydnone

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in vivo edema inducing activity, overview

3-[4-[hydroxyimino-(4'-n-butyl-phenyl)-methyl]-phenyl]-4-phenyl-sydnone

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in vivo edema inducing activity, overview

3-[4-[hydroxyimino-(4'-n-butyl-phenyl)-methyl]-phenyl]-sydnone

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in vivo edema inducing activity, overview

3-[4-[hydroxyimino-(4'-n-propyl-phenyl)-methyl]-phenyl]-4-phenylsydnone

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in vivo edema inducing activity, overview

3-[4-[hydroxyimino-(4'-n-propyl-phenyl)-methyl]-phenyl]-sydnone

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in vivo edema inducing activity, overview

Acetic anhydride

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loss of both enzymatic and toxic properties

aristolochic acid

show

Ba2+

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luffariellin B

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manoalogue

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synthetic analogue of the sea sponge-derived manoalide, time dependent irreversible loss of activity: modification of lysine residues

methyl arachidonyl fluorophosphonate

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almost complete inhibition

omega-bromo-4-nitroacetophenone

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p-bromophenacyl bromide

show

Sr2+

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competitive inhibition

turmerin

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inhibits the enzymatic activity and neutralises the pharmacological properties, such as cytotoxicity, oedema and myotoxicity of multitoxic phospholipase A2 of cobra venom in a dose-dependent manner, at a 1:2.5 molar ratio of PLA2:turmerin

Withania somnifera glycoprotein WSG

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in molar ratio of 1:2, enzyme:WSG, complete inhibition of activity, but not neutralization of toxicity

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Go to Activating Compound Search

phosphatidylcholine

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activates hydrolysis of phosphatidylethanolamine

sphingomyelin

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activates hydrolysis of phosphatidylethanolamine

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Go to KM Value Search

0.19

1-palmitoyl-2-(12-(3-(4-hydroxyphenyl)propionyl)amino dodecanoyl)phosphatidylcholine

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pH 8.5, 30°C

2 - 5

phosphatidylcholine

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Triton X-100/phospholipid: 2/1

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Go to Specific Activity Search

1100

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phospholipid/Triton X-100: 1/4

1129

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substrate: 1,2-diacyl-phosphatidylcholine

123

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isoform NN-XI-PLA2, 37°C

138

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isoform NN-XIa-PLA2, 37°C

1670

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phospholipid/Triton X-100: 1/3

2000

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Triton X-100/phospholipid: 2/1

2100

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phospholipid/Triton X-100: 1/2

34

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pH 7.5

additional information

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sensitive activity assay using radioiodinatable long-chain phosphatidylcholine, detection limit is 0.25 ng enzyme or 0.05 ng substrate

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Go to pH Optimum Search

7.5

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indirect hemolytic assay at

8

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enzymatic assay at

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Go to pH Range Search

7 - 9

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substrate: 1,2-diacyl-phosphatidylcholine

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Go to Temperature Optimum Search

37

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assay at

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Go to Organism Search

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show

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Go to Localization Search

show

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Go to General Information Search

physiological function

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PLA2 induces cytotoxic effect on human peripheral lymphocytes. Increased creatine kinase levels (myonecrosis) in the group of mice treated with PLA2

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Go to AA Sequence and Transmembrane Helices SearchGo to Localization Prediction

PA2A2_NAJNA

119

0

13346

Swiss-Prot

other Location (Reliability: 3)

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Go to PDB and Structure Links Search

show

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Go to Molecular Weight Search

10000

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x * 10000, SDS-PAGE

13000

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gel filtration, SDS-PAGE, analytical ultracentrifugation

13262

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x * 13262, MALDI-MS

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Go to Subunit Search

trimer

show

?

show

dimer

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2 * 13000, identical subunits, gel filtration, SDS-PAGE, analytical ultracentifugation, dimerization occurs at enzyme concentrations between 0.1 and 2 mg PLA2 per ml

monomer

show

polymer

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13000, identical subunits, gel filtration, SDS-PAGE, analytical ultracentifugation, polimerization at enzyme concentrations above 5mg PLA2 per ml

trimer

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observed in crystal, no data concerning MW

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Go to Crystallization (commentary) Search

PLA2 in complex with inhibitor minocycline, by hanging drop vapor diffusion method, at 1.65 A resolution. Belongs to space group P213 with unit cell parameters a = 68.712 A, b = 68.712 A, c = 68.712 A. Minocycline binds to the hydrophobic cleft at the entrance of the active site of PLA2. As a consequence, the access of substrate molecules to the active site is blocked, and the conformation of the Ca2+-binding loop is stabilized in the Ca2+-free conformation of the apo-enzyme, thus resulting in inhibition of enzymatic activity. Interaction between PLA2 and minocycline is mainly hydrophobic

two crystal forms, cubic crystal: 1.8 A resolution and R-factor of 17%, orthorhombic form: 2.65 A resolution and R-factor of 21%

x-ray crystal structure, 6.0-2.3 A resolution, R-factor of 0.174, 148 water molecules included

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Go to Temperature Stability Search

100

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for 10 min at pH 3-4, only 5% loss in activity

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Go to General Stability Search

guanidine-HCL, PLA2 retains 60% of activity when assay contains 6 M of guanidine-HCl

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Go to Organic Solvent Search

Acetone

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PLA2 regains almost full activity when added to assay mixture

benzene

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PLA2 regains almost full activity when added to assay mixture

chloroform

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PLA2 regains almost full activity when added to assay mixture

ether

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PLA2 regains almost full activity when added to assay mixture

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Go to Storage Stability Search

-20°C

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4°C, pH 7.5, 0.05 M sodium phosphate buffer, no loss of activity over a period of several months

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frozen, PLA2 concentration below 2 mg/ml, no loss of activity or precipitation for up to 12 months

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Go to Purification (commentary) Search

by centrifugation and on anion-exchange column

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by gel filtration

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column chromatography, 15fold

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Go to Cloned (commentary) Search

PLA2 injected (subcutaneous) into the right hind paw of mice

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Go to Application Search

drug development

applicability of minocycline as a lead compound for the design of specific inhibitors of PLA2, which play a crucial role in inflammatory processes

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top print hide References Search

Ghomashchi, F.; Yu, B.Z.; Mihelich, E.D.; Jain, M.K.; Gelb, M.H.

Kinetic characterization of phospholipase A2 modified by manoalogue

Biochemistry

30

9559-9569

1991

Apis mellifera, Naja naja, Sus scrofa

Manually annotated by BRENDA team

Hoffman, W.J.; Vahey, M.; Hajdu, J.

Pancreatic porcine phospholipase A2 catalyzed hydrolysis of phosphatidylcholine in lecithin-bile salt mixed micelles: Kinetic studies in a lecithin-sodium cholate system

Arch. Biochem. Biophys.

221

361-370

1983

Naja naja, Sus scrofa

Manually annotated by BRENDA team

Deems, R.A.; Dennis, E.A.

Phospholipase A2 from cobra venom (Naja naja naja)

Methods Enzymol.

71

703-710

1981

Naja naja

Manually annotated by BRENDA team

Segelke, B.W.; Nguyen, D.; Chee, R.; Xuong, N.H.; Dennis, E.A.

Structures of two novel crystal forms of Naja naja naja phospholipase A2 lacking Ca2+ reveal trimeric packing

J. Mol. Biol.

279

223-232

1998

Naja naja (P15445), Naja naja

Manually annotated by BRENDA team

Fremont, D.H.; Anderson, D.H.; Wilson, I.A.; Dennis, E.A.; Xuong, N.H.

Crystal structure of phospholipase A2 from Indian cobra reveals a trimeric association

Proc. Natl. Acad. Sci. USA

90

342-346

1993

Naja naja

Manually annotated by BRENDA team

Sundell, I.B.; Aziz, K.A.; Zuzel, M.; Theakston, R.D.G.

The role of phospholipases A2 in the stimulation of neutrophil motility by cobra venoms

Toxicon

41

459-468

2003

Naja naja, Naja mossambica

Manually annotated by BRENDA team

Caramelo, J.J.; Delfino, J.M.

A subnanogram assay for phospholipase activity based on a long-chain radioiodinatable phosphatidylcholine

Anal. Biochem.

333

289-295

2004

Naja naja

Manually annotated by BRENDA team

Satish, S.; Tejaswini, J.; Krishnakantha, T.P.; Gowda, T.V.

Purification of a Class B1 platelet aggregation inhibitor phospholipase A2 from Indian cobra (Naja Naja) venom

Biochimie

86

203-210

2004

Naja naja

Manually annotated by BRENDA team

Machiah, D.K.; Gowda, T.V.

Purification of a post-synaptic neurotoxic phospholipase A2 from Naja naja venom and its inhibition by a glycoprotein from Withania somnifera

Biochimie

88

701-710

2006

Naja naja

Manually annotated by BRENDA team

Shashidharamurthy, R.; Kemparaju, K.

A neurotoxic phospholipase A(2) variant: Isolation and characterization from eastern regional Indian cobra (Naja naja) venom

Toxicon

47

727-733

2006

Naja naja

Manually annotated by BRENDA team

Burke, J.E.; Dennis, E.A.

Phospholipase A2 biochemistry

Cardiovasc. Drugs Ther.

23

49-59

2009

Apis mellifera, Bitis gabonica, Bos taurus, Crotalus sp., Homo sapiens, Mus musculus, Naja naja, Oryza sativa, Rattus norvegicus, Sus scrofa, Protoparvovirus

Manually annotated by BRENDA team

Kamble, R.R.; Belgur, S.S.; Aladkatti, R.; Khazi, I.A.

Synthesis and evaluation of benzophenone oximes derivatized with sydnone as inhibitors of secretory phospholipase A2 with anti-inflammatory activity

Chem. Pharm. Bull.

57

16-21

2009

Naja naja, Daboia russelii, Trimeresurus malabaricus

Manually annotated by BRENDA team

Chethankumar, M.; Srinivas, L.

New biological activity against phospholipase A2 by Turmerin, a protein from Curcuma longa L

Biol. Chem.

389

299-303

2008

Naja naja

Manually annotated by BRENDA team

Burke, J.; Dennis, E.

Phospholipase A2 structure/function, mechanism, and signaling

J. Lipid Res.

50 Suppl

S237-S242

2009

Apis mellifera, Homo sapiens, Mus musculus, Naja naja

Manually annotated by BRENDA team

Dalm, D.; Palm, G.J.; Aleksandrov, A.; Simonson, T.; Hinrichs, W.

Nonantibiotic properties of tetracyclines: structural basis for inhibition of secretory phospholipase A2

J. Mol. Biol.

398

83-96

2010

Naja naja (P15445), Naja naja

Manually annotated by BRENDA team

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InterPro (database of protein families, domains and functional sites)

Transporter Classification Database (TCDB): 1.N.2.1.6, 1.B.84.1.6, 1.B.84.1.5, 1.B.84.1.3, 1.B.84.1.1, 1.B.84.1.4, 1.B.84.1.2

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Release 2023.1 (January 2023)