Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2103)
Drug Name
L-arginine
Synonyms
ARGININE, L-; Argamine; Arginina; Arginina [INN-Spanish]; Arginine (VAN); Arginine [USAN:INN]; Argininum [INN-Latin]; Argivene; Detoxargin; H-Arg-OH; L(+)-Arginine; L-(+)-Arginine; L-Arginin; L-Arginine, homopolymer; L-arginine; Levargin; Minophagen A; Poly(L-arginine); Polyarginine; arginine; (L)-Arginine; (S)-2-Amino-5-guanidinopentanoic acid; 1-Amino-4-guanidovaleric acid; 74-79-3; AI3-24165; CCRIS 3609; HSDB 1429; L-Arg; L-Ornithine, N5-(aminoiminomethyl)-; L-alpha-Amino-delta-guanidinovaleric acid; NSC 206269; UNII-94ZLA3W45F; arg
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 174.2 Topological Polar Surface Area 128
Heavy Atom Count 12 Rotatable Bond Count 5
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
6322
PubChem SID
3362 ; 653149 ; 819917 ; 819921 ; 826172 ; 830289 ; 832441 ; 3132036 ; 3727089 ; 6436672 ; 7980746 ; 8026405 ; 8144863 ; 10318557 ; 10322713 ; 10534673 ; 11110746 ; 11113629 ; 14715928 ; 14716352 ; 14716357 ; 14716362 ; 14716368 ; 14716374 ; 14716380 ; 14716386 ; 14716395 ; 14772629 ; 14772631 ; 17397138 ; 17404640 ; 22390401 ; 24278014 ; 24890870 ; 24891316 ; 24901894 ; 26703087 ; 26703289 ; 26705873 ; 26707942 ; 26713060 ; 26713062 ; 26718638 ; 26718983 ; 29203857 ; 29225313 ; 46392409 ; 46507180 ; 47291278 ; 49701063
ChEBI ID
CHEBI:16467
CAS Number
157-06-2
TTD Drug ID
D0O3VV
Formula
C6H14N4O2
Canonical SMILES
C(CC(C(=O)O)N)CN=C(N)N
InChI
1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1
InChIKey
ODKSFYDXXFIFQN-BYPYZUCNSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Asymmetric dimethylarginine DM004950
123831
Conjugation - Methylationn 1 [4] , [5]
L-Monomethylarginine DM004949
132862
Conjugation - Methylationn 1 [4] , [5]
Symmetric dimethylarginine DM004951
169148
Conjugation - Methylationn 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005365 L-arginine L-Monomethylarginine Conjugation - Methylationn PRMT1 ... [4], [5]
MR005366 L-arginine Asymmetric dimethylarginine Conjugation - Methylationn PRMT1 [4], [5]
MR005367 L-arginine Symmetric dimethylarginine Conjugation - Methylationn PRMT2 [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arginine dihydrolase (arcA) DME1949 Staphylococcus petrasii
A0A380FWY5_9STAP
3.5.3.6
[2]
Liver-type arginase (ARG1) DME0489 Homo sapiens
ARGI1_HUMAN
3.5.3.1
[3]
Protein arginine N-methyltransferase 1 (PRMT1) DMEN249 Homo sapiens
ANM1_HUMAN
2.1.1.319
[4] , [5]
Protein arginine N-methyltransferase 2 (PRMT2) DMEN250 Homo sapiens
ANM2_HUMAN
2.1.1.319
[4] , [5]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Liver-type arginase (ARG1) DME0489 Km = 0.02 microM
ARGI1_HUMAN
[3]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 721).
2 Staphylococcus jettensis sp. nov., a coagulase-negative staphylococcal species isolated from human clinical specimens. Int J Syst Evol Microbiol. 2013 Sep;63(Pt 9):3250-6.
3 Crystal structure of human arginase I at 1.29-A resolution and exploration of inhibition in the immune response. Proc Natl Acad Sci U S A. 2005 Sep 13;102(37):13058-63.
4 Chromatographic-mass spectrometric methods for the quantification of L-arginine and its methylated metabolites in biological fluids
5 Quantitative assessment of arginine methylation in free versus protein-incorporated amino acids in vitro and in vivo using protein hydrolysis and high-performance liquid chromatography

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