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(4-Aminobutyl)guanidine

AlkaPlorer ID: AK012388

Synonym: 4-Guanidinobutylamine, 1-Amino-4-guanidinobutane, Agmatine

IUPAC Name: 2-(4-aminobutyl)guanidine

Structure

SMILES: N=C(N)NCCCCN

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InChI: InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)

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InChIKey: QYPPJABKJHAVHS-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Grindelia havardii Grindelia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Capparis masaikai Capparis Capparaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Astragalus oxyphysus Astragalus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polyscias scutellaria Polyscias Araliaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cuscuta reflexa Cuscuta Convolvulaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Plantago depressa Plantago Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ambrosia artemisiifolia Ambrosia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Tapes Veneridae Venerida Bivalvia Mollusca Metazoa Eukaryota
Claviceps purpurea Claviceps Clavicipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Homo sapiens Homo Hominidae Primates Mammalia Chordata Metazoa Eukaryota
Centaurea glastifolia Centaurea Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nephelium maingayi Nephelium Sapindaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Galanthus nivalis Galanthus Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hydrodictyon reticulatum Hydrodictyon Hydrodictyaceae Sphaeropleales Chlorophyceae Chlorophyta Viridiplantae Eukaryota
Prunus dulcis Prunus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mus musculus Mus Muridae Rodentia Mammalia Chordata Metazoa Eukaryota
Anthopleura japonica Anthopleura Actiniidae Actiniaria Anthozoa Cnidaria Metazoa Eukaryota
Senecio candollei Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Escherichia coli Escherichia Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Verbesina caracasana Verbesina Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Pyrus pyraster Pyrus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 130.195

TPSA？: 87.92

MolLogP？: -0.7916300000000003

Number of H-Donors: 4

Number of H-Acceptors: 2

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 2511.9 nM None
Homo sapiens Arachidonate 15-lipoxygenase Potency 12589.3 nM None
Homo sapiens Cytochrome P450 1A2 AC50 31622.78 nM None
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Histone deacetylase 6 Inhibition -26.47 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -1.13 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 5623.4 nM None
Homo sapiens Monoamine oxidase A IC50 100000.0 nM None
Homo sapiens Monoamine oxidase B IC50 100000.0 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 354.8 nM None
Homo sapiens Solute carrier family 22 member 1 Activity nan None 10.1124/jpet.102.044404
Homo sapiens Solute carrier family 22 member 1 Inhibition 2.1 % 10.1021/jm8003152
Homo sapiens Solute carrier family 22 member 1 Ki 24000000.0 nM 10.1124/jpet.102.044404
Homo sapiens Solute carrier family 22 member 2 Km 1400000.0 nM 10.1124/jpet.102.044404
Homo sapiens Solute carrier family 22 member 3 Km 2500000.0 nM 10.1124/jpet.102.044404
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 6683.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 8414.4 nM None
Rattus norvegicus Adrenergic receptor alpha-2 Ki 31700.0 nM 10.1016/j.bmc.2010.11.039
Rattus norvegicus Adrenergic receptor alpha-2 Ki 31700.0 nM 10.1016/j.bmcl.2008.11.055
Rattus norvegicus Deoxyhypusine synthase IC50 156000.0 nM 10.1021/jm00016a008
Rattus norvegicus Nischarin IC50 36532.0 nM 10.1016/j.bmc.2010.11.039
Rattus norvegicus Nischarin IC50 36532.0 nM 10.1016/j.bmcl.2008.11.055
Rattus norvegicus Rattus norvegicus Blood Pressure nan None 10.1021/jm021050c
Rattus norvegicus Rattus norvegicus Change -10.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Rattus norvegicus Change -8.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Rattus norvegicus Change 0.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Rattus norvegicus Change 12.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Rattus norvegicus Change 14.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Rattus norvegicus Change 16.0 % 10.1016/s0960-894x(99)00569-7
Rattus norvegicus Solute carrier family 22 member 1 Activity nan None 10.1124/jpet.102.044404
Rattus norvegicus Solute carrier family 22 member 1 Ki 8600000.0 nM 10.1124/jpet.102.044404
Rattus norvegicus Solute carrier family 22 member 2 Km 950000.0 nM 10.1124/jpet.102.044404
Rattus norvegicus Solute carrier family 22 member 3 Km 900000.0 nM 10.1124/jpet.102.044404
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 562.3 nM None
Trypanosoma cruzi Cruzipain Potency 39810.7 nM None
Zea mays Polyamine oxidase Ki 3000.0 nM 10.1021/jm900371z
None Unchecked Ki 416700.0 nM 10.1016/j.bmc.2010.11.039
None Unchecked Ki 416700.0 nM 10.1016/j.bmcl.2008.11.055
None Unchecked Potency 14125.4 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000832 *OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(=N)nc2NCCCCNC(=N)N)[C@H](O)[C@@H]1OP(=O)(O)O*>>N=C(N)NCCCCN MNXR187804
AKRT000834 *OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)O*.N=C(N)NCCCCN>>*OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(=N)nc2NCCCCNC(=N)N)[C@H](O)[C@@H]1OP(=O)(O)O* RXN-14344
AKRT002427 CC(=O)NCCCCNC(=N)N>>N=C(N)NCCCCN enzymemap_77439
AKRT007123 CCC(=O)NCCCCNC(=N)N>>N=C(N)NCCCCN enzymemap_77440
AKRT011482 COc1cc(/C=C/C(=O)[32S])ccc1O.N=C(N)NCCCCN>>COc1cc(/C=C/C(=O)NC(=N)NCCCCN)ccc1O None
AKRT011483 COc1cc(/C=C/C(=O)[32S])ccc1O.N=C(N)NCCCCN>>COc1cc(/C=C/C(=O)NCCCCNC(=N)N)ccc1O None
AKRT011491 COc1cc(/C=C/C(=O)[CoA])cc(OC)c1O.N=C(N)NCCCCN>>COc1cc(/C=C/C(=O)NCCCCNC(=N)N)cc(OC)c1O enzymemap_31603
AKRT011503 COc1cc(/C=C/C(=O)[CoA])ccc1O.N=C(N)NCCCCN>>COc1cc(/C=C/C(=O)NC(=N)NCCCCN)ccc1O enzymemap_28802
AKRT011504 COc1cc(/C=C/C(=O)[CoA])ccc1O.N=C(N)NCCCCN>>COc1cc(/C=C/C(=O)NCCCCNC(=N)N)ccc1O R09255
AKRT014472 C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N=C(N)NCCCCN>>N=C(N)NCCCCNCCCN RXN-12514
AKRT014815 Cc1c(N)nc([C@H](CC(N)=O)NC[C@H](N)C(N)=O)nc1C(=O)N[C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@H](C(=O)NCCc1nc(-c2nc(C(=O)NCCCCNC(=N)N)cs2)cs1)[C@@H](C)O)[C@@H](O[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]1O)c1cnc[nH]1>>N=C(N)NCCCCN enzymemap_77438
AKRT015891 N=C(N)NCCCCN.NC(N)=O>>N=C(N)NCCCCNC(=N)N DIGUANIDINOBUTANASE-RXN
AKRT015892 N=C(N)NCCCCN.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1>>N=C(N)NCCCCNc1nc(=N)ccn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RXN-16944
AKRT015893 N=C(N)NCCCCN.O=C(O)O>>N=C(N)NCCC[C@H](N)C(=O)O MNXR136489
AKRT015894 N=C(N)NCCCCN.O=C(O)c1ccccc1>>N=C(N)NCCCCNC(=O)c1ccccc1 ACYLAGMATINE-AMIDASE-RXN
AKRT015895 N=C(N)NCCCCN.O=C([32S])/C=C/c1ccc(O)cc1>>N=C(N)NCCCCNC(=O)/C=C/c1ccc(O)cc1 None
AKRT015896 N=C(N)NCCCCN.O=C([CoA])/C=C/c1ccc(O)cc1>>N=C(N)NCCCCNC(=O)/C=C/c1ccc(O)cc1 R01617
AKRT015897 N=C(N)NCCCCN.O=C([CoA])/C=C/c1ccc(O)cc1>>NC(N)=NCCCCNC(=O)/C=C/c1ccc(O)cc1 AGMATINE-N4-COUMAROYLTRANSFERASE-RXN
AKRT015898 N=C(N)NCCCCN>>N=C(N)N1CCC[C@H]1O 69160
AKRT015899 N=C(N)NCCCCN>>N=C(N)NCCCC=O 69144
AKRT015900 N=C(N)NCCCCN>>N=C(N)NCCCCNP(=O)(O)O AGMATINE-KINASE-RXN
AKRT015901 N=C(N)NCCCCN>>NC(N)=O AGMATIN-RXN
AKRT015902 N=C(N)NCCCCN>>NC(N)=O.NCCCCN None
AKRT015903 N=C(N)NCCCCN>>NCCCCN AGMATIN-RXN
AKRT015904 N=C(N)NCCCCN>>NCCCCNC(N)=O AGMATINE-DEIMINASE-RXN
AKRT015905 N=C(N)NCCCCNC(=N)N>>N=C(N)NCCCCN DIGUANIDINOBUTANASE-RXN
AKRT015908 N=C(N)NCCCCNC(=O)c1ccccc1>>N=C(N)NCCCCN ACYLAGMATINE-AMIDASE-RXN
AKRT015911 N=C(N)NCCCCNP(=O)(O)O>>N=C(N)NCCCCN AGMATINE-KINASE-RXN
AKRT015912 N=C(N)NCCCCNc1nc(=N)ccn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>N=C(N)NCCCCN RXN-16944
AKRT016089 N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCCCN ARGDECARBOX-RXN
AKRT016090 N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCCCN.O=C=O None
AKRT017993 NCCCCNC(N)=O>>N=C(N)NCCCCN None
AKRT023409 O=C([CoA])/C=C/c1ccc(O)c(O)c1.N=C(N)NCCCCN>>N=C(N)NCCCCNC(=O)/C=C/c1ccc(O)c(O)c1 enzymemap_31605
AKRT023410 O=C([CoA])/C=C/c1ccc(O)c(O)c1.N=C(N)NCCCCN>>N=C(NCCCCN)NC(=O)/C=C/c1ccc(O)c(O)c1 enzymemap_31605
AKRT023422 O=C([CoA])/C=C/c1ccc(O)cc1.N=C(N)NCCCCN>>N=C(N)NCCCCNC(=O)/C=C/c1ccc(O)cc1 enzymemap_31597
AKRT023436 O=C([CoA])/C=C/c1ccccc1.N=C(N)NCCCCN>>N=C(N)NCCCCNC(=O)/C=C/c1ccccc1 enzymemap_31604