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

General Information of Drug (ID: DR0052)
Drug Name
Agmatine
Synonyms
Argmatine; N-(4-aminobutyl)guanidine; N-4-Aminobutylguanidine; QYPPJABKJHAVHS-UHFFFAOYSA-N; Tocris-0842; agmatine; agmatinium; guanidine, (4-aminobutyl)-; (4-Aminobutyl) guanidine; (4-Aminobutyl)guanidine; .Agmatin; 1,4-Butanediamine, N-(aminoiminomethyl)-; 1-(4-Aminobutyl)guanidine; 1-Amino-4-guanidinobutane; 1-Amino-4-guanidobutane; 2-(4-aminobutyl)guanidine; 306-60-5; 4-Guanidino-1-butanamine; 70J407ZL5Q; AG2; CHEBI:17431; CHEMBL58343; EINECS 206-187-7; Guanidine, (4-aminobutyl)- (8CI)(9CI); NSC 56332; UNII-70J407ZL5Q
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 130.19 Topological Polar Surface Area 90.4
Heavy Atom Count 9 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
199
PubChem SID
3479 ; 105761 ; 3134912 ; 6490744 ; 7885760 ; 7980025 ; 8144144 ; 11110769 ; 11113734 ; 11341771 ; 11361954 ; 11364550 ; 11364959 ; 11367112 ; 11367521 ; 11369674 ; 11370083 ; 11373122 ; 11375630 ; 11375683 ; 11377836 ; 11378254 ; 11485351 ; 11487356 ; 11489424 ; 11493719 ; 11495470 ; 11537788 ; 15194512 ; 24438576 ; 26708719 ; 26708826 ; 26751919 ; 26751920 ; 47662500 ; 47959962 ; 47959963 ; 49655355 ; 49655358 ; 49746689 ; 49974254 ; 50067025 ; 50104596 ; 51021788 ; 56312408 ; 56314364 ; 57320033 ; 85164909 ; 87326004 ; 88835865
ChEBI ID
CHEBI:17431
CAS Number
306-60-5
TTD Drug ID
D0K7CV
Formula
C5H14N4
Canonical SMILES
C(CCN=C(N)N)CN
InChI
1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)
InChIKey
QYPPJABKJHAVHS-UHFFFAOYSA-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
Gamma-guanidinobutyraldehyde DM001726
25200663
Unclear 1 [3]
Hydrogen peroxide DM001730
784
Unclear 1 [3]
Putrescine DM003089
1045
Unclear 1 [3] , [6] , [7]
Urea DM001344
1176
Unclear 1 [3]
Gamma-guanidinobutyrate DM001727
500
Unclear 2 [3]
MTA DM001725
439176
Unclear 2 [3]
NADH DM001729
439153
Unclear 2 [3]
SPD DM001721
1102
Unclear 2 [3] , [6] , [7]
#NAME? DM000332
119
Unclear 3 [3]
MTA DM001725
439176
Unclear 3 [3]
N1-AcSpd DM001724 N. A. Unclear 3 [3]
Spermine DM001722
1103
Unclear 3 [3] , [6] , [7]
Urea DM001344
1176
Unclear 3 [3] , [8]
N-AcSpm DM001723 N. A. Unclear 4 [3]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003066 Agmatine Putrescine Unclear Unclear [3], [6], [7]
MR003072 Agmatine Gamma-guanidinobutyraldehyde Unclear AOC1 [3]
MR003078 Agmatine Urea Unclear Unclear [3]
MR003079 Agmatine H2O2 Unclear Unclear [3]
MR003073 Gamma-guanidinobutyraldehyde Gamma-guanidinobutyrate Unclear ALDH1A1A1A1 [3]
MR003076 Gamma-guanidinobutyraldehyde NADH Unclear Unclear [3]
MR003067 Putrescine Spermidine Unclear Unclear [3], [6], [7]
MR003077 Putrescine MTA Unclear SMS [3]
MR003074 Gamma-guanidinobutyrate Gamma-aminobutyrate Unclear PLD1 [3]
MR003075 Gamma-guanidinobutyrate Urea Unclear Unclear [3], [8]
MR003068 Spermidine Spermine Unclear Unclear [3], [6], [7]
MR003070 Spermidine N1-AcSpd Unclear BleG1_1835 ... [3]
MR003071 Spermidine MTA Unclear SMS [3]
MR003069 Spermine N-AcSpm Unclear BleG1_1835 ... [3]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Agmatine ureohydrolase (AGMAT) DME0587 Homo sapiens
SPEB_HUMAN
3.5.3.11
[2]
Aldehyde dehydrogenase 1 (ALDH1) DME0286 Homo sapiens
AL1A1_HUMAN
1.2.1.36
[3]
Amiloride-sensitive amine oxidase (AOC1) DME0404 Homo sapiens
AOC1_HUMAN
1.4.3.22
[3]
Choline phosphatase 1 (PLD1) DME0194 Homo sapiens
PLD1_HUMAN
3.1.4.4
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Permidine/putrescine ABC transporter substrate-binding protein (BleG1_1835) DMEN036 Bacillus pumilus
A0A060M1I7_9BACI
3.1.1.1
[3]
Poly [ADP-ribose] polymerase 3 (PARP3) DME0594 Homo sapiens
PARP3_HUMAN
2.4.2.30
[5]
Spermidine N(1)-acetyltransferase (speG) DMEN037 Escherichia coli
ATDA_ECOLI
1.17.1.4
[3]
Spermine synthase (SMS) DMEN038 Homo sapiens
SPSY_HUMAN
1.14.13.39
[3]
⏷ Show the Full List of 9  DME(s)
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: 4127).
2 Metabolic strategies for the degradation of the neuromodulator agmatine in mammals. Metabolism. 2018 Apr;81:35-44.
3 Metabolism and function in animal tissues of agmatine, a biogenic amine formed from arginine Amino Acids. 2004 Feb;26(1):3-8. doi: 10.1007/s00726-003-0030-z.
4 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
5 Mono-ADP-ribosylation catalyzed by arginine-specific ADP-ribosyltransferases. Methods Mol Biol. 2018;1813:149-165.
6 Genome-wide analysis of polyamine biosynthesis genes in wheat reveals gene expression specificity and involvement of STRE and MYB-elements in regulating polyamines under drought. BMC Genomics. 2022 Oct 30;23(1):734. doi: 10.1186/s12864-022-08946-2.
7 Unique Chemistry, Intake, and Metabolism of Polyamines in the Central Nervous System (CNS) and Its Body. Biomolecules. 2022 Mar 25;12(4):501. doi: 10.3390/biom12040501.
8 A guanidine-degrading enzyme controls genomic stability of ethylene-producing cyanobacteria. Nat Commun. 2021 Aug 26;12(1):5150. doi: 10.1038/s41467-021-25369-x.

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