2.5.1.96: 4,4'-diapophytoene synthase
This is an abbreviated version!
For detailed information about 4,4'-diapophytoene synthase, go to the full flat file.
Word Map on EC 2.5.1.96
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2.5.1.96
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staphylococcus
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aureus
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carotenoid
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staphyloxanthin
-
desaturase
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head-to-head
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4,4'-diaponeurosporene
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allyl
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carbocation
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desaturation
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dimethylallyl
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head-to-tail
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synthesis
- 2.5.1.96
- staphylococcus
- aureus
-
carotenoid
- staphyloxanthin
-
desaturase
-
head-to-head
- 4,4'-diaponeurosporene
-
allyl
-
carbocation
-
desaturation
-
dimethylallyl
-
head-to-tail
- synthesis
Reaction
2 (2E,6E)-farnesyl diphosphate = + 2 diphosphate
Synonyms
CrtM, DAP synthase, dehydrosqualene synthase, diapophytoene synthase, DSQ synthase, DSQS
ECTree
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Inhibitors
Inhibitors on EC 2.5.1.96 - 4,4'-diapophytoene synthase
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(3R)-3-biphenyl-4-yl-1-azabicyclo[2.2.2]octan-3-ol
i.e. BPH-651, forms two crystal structures in complex with the enzyme. In both, the quinuclidine headgroup binds in the allylic S1 site with the side chain in S2, but in the presence of diphosphate and Mg2+, the quinuclidine's cationic center interacts with diphosphate and three Mg2+, mimicking a transition state involved in diphosphate ionization
(S)-1-phosphono-4-(3-phenoxyphenyl)butylsulfonic acid
far more active than (R)-compound both in vitro an in cells
([[(E)-[[(3E)-4,8-dimethylnona-3,7-dien-1-yl](methyl)iminio]methyl]amino]methyl)(phosphonomethyl)phosphinate
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competitive inhibitor
1-phosphono-4-[3-(3,4-difluorophenoxy)phenyl]butylsulfonic acid
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1-phosphono-4-[3-(4-propylphenoxy)phenyl]butylsulfonic acid
potent inhibitor in cell-based assay
2-(4-phenoxyphenoxy)ethyl thiocyanate
i.e. WC-9, binds to the S2 site with its -SCN group surrounded by four hydrogen bond donors
4-(3-phenoxyphenyl)-1-phosphonobutane-1-sulfonic acid
i.e. BPH-652
4-(4'-butylbiphenyl-4-yl)-1-phosphonobutane-1-sulfonic acid
i.e. BPH-698
4-(biphenyl-4-yl)-1-phosphonobutane-1-sulfonic acid
i.e. BPH-700
lapaquistat acetate
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docking analysis, interaction with residues H18, R45, D48, D52, Y129, Q165, N168 and D172
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N'-[(1R,3S,5R,7R)-tricyclo[3.3.1.1-3,7-]dec-2-yl]ethane-1,2-diamine
i.e. SQ-109, forms two crystal structurs in complex with the enzyme. In one, the geranyl side chain binds to either S1 or S2 and the adamantane headgroup binds to S1. In the second, the side chain binds to S2 while the headgroup binds to S1
squalestatin
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docking analysis, interaction with residues H18, R45, D48, D52, Y129, Q165, N168 and D172
[([(E)-amino[(4,8-dimethylnonyl)(methyl)iminio]methyl]amino)methyl](phosphonomethyl)phosphinate
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competitive inhibitor
[[([[(4,8-dimethylnonyl)(methyl)carbamoyl]amino]methyl)(hydroxy)phosphoryl]methyl]phosphonic acid
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competitive inhibitor