Literature summary for 3.5.3.18 extracted from

Wang, Y.; Monzingo, A.F.; Hu, S.; Schaller, T.H.; Robertus, J.D.; Fast, W.
Developing dual and specific inhibitors of dimethylarginine dimethylaminohydrolase-1 and nitric oxide synthase: toward a targeted polypharmacology to control nitric oxide (2009), Biochemistry, 48, 8624-8635.

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Cloned(Commentary)

Cloned (Comment)	Organism
-	Homo sapiens

Crystallization (Commentary)

Crystallization (Comment)	Organism
N5-(1-iminopropyl)-L-ornithine:DDAH-1 complex, to 1.9 A resolution, covalent bond formation between the inhibitors amidino carbon and the active-site Cys274, and solution studies show reversible competitive inhibition, consistent with a reversible covalent mode of DDAH inhibition by alkylamidine inhibitors	Homo sapiens

Inhibitors

Inhibitors	Comment	Organism	Structure
L-arginine	-	Homo sapiens
L-citrulline	-	Homo sapiens
additional information	S-ethyl-2-thiopseudourea, S-ethyl-N-phenylisothiourea and phenylene-1,3-bis(ethane-2-isothiourea) do not inhibit DDAH-1 at concentrations below 1 mM	Homo sapiens
N5-(1-iminoethyl)-L-ornithine	-	Homo sapiens
N5-(1-iminohexyl)-L-ornithine	-	Homo sapiens
N5-(1-iminopentyl)-L-ornithine	-	Homo sapiens
N5-(1-iminopropyl)-L-ornithine	crystallization data. Reversible competitive inhibition, consistent with a reversible covalent mode of DDAH inhibition by alkylamidine inhibitors	Homo sapiens

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
0.0014	-	S-methyl-L-thiocitrulline	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0031	-	S-methyl-L-thiocitrulline	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0036	-	S-methyl-L-thiocitrulline	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.019	-	S-methyl-L-thiocitrulline	mutant E78AA, pH 7.3, temperature not specified in the publication	Homo sapiens
0.11	-	Nomega,Nomega-dimethyl-L-arginine	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens
0.75	-	Nomega,Nomega-dimethyl-L-arginine	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
1.4	-	Nomega,Nomega-dimethyl-L-arginine	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
13.7	-	Nomega,Nomega-dimethyl-L-arginine	mutant E78A, pH 7.3, temperature not specified in the publication	Homo sapiens

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	O94760	isoform DDAH-1	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
additional information	no substrate: S-ethyl-2-thiopseudourea, S-ethyl-N-phenylisothiourea and phenylene-1,3-bis(ethane-2-isothiourea)	Homo sapiens	?	-	?
Nomega,Nomega-dimethyl-L-arginine + H2O	-	Homo sapiens	dimethylamine + L-citrulline	-	?
S-methyl-L-thiocitrulline + H2O	-	Homo sapiens	L-citrulline + methanethiol	-	?

Synonyms

Synonyms	Comment	Organism
DDAH-1	-	Homo sapiens

Turnover Number [1/s]

Turnover Number Minimum [1/s]	Turnover Number Maximum [1/s]	Substrate	Comment	Organism	Structure
0.0015	-	Nomega,Nomega-dimethyl-L-arginine	mutant E78A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0087	-	Nomega,Nomega-dimethyl-L-arginine	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0097	-	S-methyl-L-thiocitrulline	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
0.014	-	Nomega,Nomega-dimethyl-L-arginine	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0163	-	Nomega,Nomega-dimethyl-L-arginine	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.03	-	S-methyl-L-thiocitrulline	mutant E78AA, pH 7.3, temperature not specified in the publication	Homo sapiens
0.042	-	S-methyl-L-thiocitrulline	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.042	-	S-methyl-L-thiocitrulline	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.0075	-	pH 7.3, temperature not specified in the publication	Homo sapiens	N5-(1-iminopentyl)-L-ornithine
0.052	-	pH 7.3, temperature not specified in the publication	Homo sapiens	N5-(1-iminopropyl)-L-ornithine
0.11	-	pH 7.3, temperature not specified in the publication	Homo sapiens	N5-(1-iminohexyl)-L-ornithine
0.131	-	pH 7.3, temperature not specified in the publication	Homo sapiens	L-arginine
0.99	-	pH 7.3, temperature not specified in the publication	Homo sapiens	N5-(1-iminoethyl)-L-ornithine
3.7	-	pH 7.3, temperature not specified in the publication	Homo sapiens	L-citrulline

kcat/KM [mM/s]

kcat/KM Value [1/mMs^-1]	kcat/KM Value Maximum [1/mMs^-1]	Substrate	Comment	Organism	Structure
0.00012	-	Nomega,Nomega-dimethyl-L-arginine	mutant E78A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0115	-	Nomega,Nomega-dimethyl-L-arginine	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
0.0116	-	Nomega,Nomega-dimethyl-L-arginine	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
0.127	-	Nomega,Nomega-dimethyl-L-arginine	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens
1.58	-	S-methyl-L-thiocitrulline	mutant E78AA, pH 7.3, temperature not specified in the publication	Homo sapiens
6.83	-	S-methyl-L-thiocitrulline	mutant L271G, pH 7.3, temperature not specified in the publication	Homo sapiens
11.7	-	S-methyl-L-thiocitrulline	mutant L30A, pH 7.3, temperature not specified in the publication	Homo sapiens
13.55	-	S-methyl-L-thiocitrulline	wild-type, pH 7.3, temperature not specified in the publication	Homo sapiens

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Release 2023.1 (January 2023)