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2-amino-5-[(E)-[amino(nitroamino)methylidene]amino]pentanoic acid

AlkaPlorer ID: AK321847

Synonym: None

IUPAC Name: (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoic acid

Structure

SMILES: N=C(NCCC[C@H](N)C(=O)O)N[N+](=O)[O-]

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InChI: InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1

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InChIKey: MRAUNPAHJZDYCK-BYPYZUCNSA-N

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Properties Information

Molecule Weight: 219.201

TPSA？: 154.37

MolLogP？: -1.5158299999999985

Number of H-Donors: 5

Number of H-Acceptors: 5

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Nitric-oxide synthase, endothelial Activity 5.0 % 10.1016/j.ejmech.2008.12.007
Bos taurus Nitric-oxide synthase, endothelial IC50 1200.0 nM 10.1021/jm980073h
Bos taurus Nitric-oxide synthase, endothelial Ki 720.0 nM 10.1021/jm061305c
Bos taurus Nitric-oxide synthase, endothelial Ki 750.0 nM 10.1021/jm100947x
Homo sapiens Bloom syndrome protein Potency 1778.3 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 DNA-(apurinic or apyrimidinic site) lyase Potency 1258.9 nM None
Homo sapiens Histone deacetylase 6 Inhibition 0.7097 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 3.71 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 103.83 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 670.2 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 70794.6 nM None
Homo sapiens N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 Inhibition 6.0 % 10.1016/j.bmc.2008.10.058
Homo sapiens Nitric-oxide synthase, brain Activity 13.0 % 10.1016/j.ejmech.2008.12.007
Homo sapiens Nitric-oxide synthase, brain IC50 80.0 nM 10.1016/s0960-894x(02)00481-x
Homo sapiens Nitric-oxide synthase, brain IC50 80.0 nM 10.1016/s0960-894x(03)00351-2
Homo sapiens Nitric-oxide synthase, brain IC50 500.0 nM 10.1021/jm970840x
Homo sapiens Nitric-oxide synthase, brain IC50 4400.0 nM 10.1021/jm900380j
Homo sapiens Nitric-oxide synthase, brain Inhibition 100.0 % 10.1016/j.bmc.2008.10.058
Homo sapiens Nitric-oxide synthase, brain Ki 15.0 nM 10.1021/jm980072p
Homo sapiens Nitric-oxide synthase, brain Ki 500.0 nM 10.1016/j.bmc.2008.04.036
Homo sapiens Nitric-oxide synthase, endothelial Activity 25.0 % 10.1016/j.ejmech.2008.12.007
Homo sapiens Nitric-oxide synthase, endothelial IC50 320.0 nM 10.1016/s0960-894x(02)00481-x
Homo sapiens Nitric-oxide synthase, endothelial IC50 320.0 nM 10.1016/s0960-894x(03)00351-2
Homo sapiens Nitric-oxide synthase, endothelial IC50 500.0 nM 10.1021/jm970840x
Homo sapiens Nitric-oxide synthase, endothelial Inhibition 100.0 % 10.1016/j.bmc.2008.10.058
Homo sapiens Nitric-oxide synthase, endothelial Ki 30.0 nM 10.1021/jm980072p
Homo sapiens Nitric-oxide synthase (endothelial and brain) Ratio 4.0 None 10.1016/s0960-894x(02)00481-x
Homo sapiens Nitric-oxide synthase (endothelial and brain) Selectivity 2.0 None 10.1021/jm980072p
Homo sapiens Nitric-oxide synthase (endothelial and brain) Selectivity 4.0 None 10.1016/s0960-894x(03)00351-2
Homo sapiens Nitric oxide synthase, inducible Activity 48.0 % 10.1016/j.ejmech.2008.12.007
Homo sapiens Nitric oxide synthase, inducible IC50 5500.0 nM 10.1016/s0960-894x(02)00481-x
Homo sapiens Nitric oxide synthase, inducible IC50 5500.0 nM 10.1016/s0960-894x(03)00351-2
Homo sapiens Nitric oxide synthase, inducible IC50 7600.0 nM 10.1021/jm970840x
Homo sapiens Nitric oxide synthase, inducible Inhibition 91.0 % 10.1016/j.bmc.2008.10.058
Homo sapiens Nitric oxide synthase, inducible Inhibition 100.0 % 10.1016/j.bmc.2008.10.058
Homo sapiens Nitric oxide synthase, inducible Ki 670.0 nM 10.1021/jm980072p
Homo sapiens Nitric oxide synthase (inducible and endothelial) Ratio 0.066 None 10.1021/jm970840x
Homo sapiens Nitric oxide sythases; iNOS & nNOS Ratio 0.066 None 10.1021/jm970840x
Homo sapiens Nitric oxide sythases; iNOS & nNOS Ratio 69.0 None 10.1016/s0960-894x(02)00481-x
Homo sapiens Nitric oxide sythases; iNOS & nNOS Selectivity 45.0 None 10.1021/jm980072p
Homo sapiens Nitric oxide sythases; iNOS & nNOS Selectivity 69.0 None 10.1016/s0960-894x(03)00351-2
Homo sapiens Peripheral myelin protein 22 Potency 84921.4 nM None
Homo sapiens Prelamin-A/C Potency 0.9 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 113.37 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 113.76 % 10.1124/mol.112.084152
Mus musculus Mus musculus Inhibition nan % 10.1016/j.bmc.2020.115733
Mus musculus Nitric-oxide synthase, brain IC50 500.0 nM 10.1016/j.bmcl.2003.11.010
Mus musculus Nitric oxide synthase, inducible Activity 8.0 % 10.1016/j.ejmech.2008.12.007
Mus musculus Nitric oxide synthase, inducible Activity 15.0 % 10.1016/j.ejmech.2008.12.007
Mus musculus Nitric oxide synthase, inducible Activity nan None 10.1016/j.ejmech.2008.12.007
Mus musculus Nitric oxide synthase, inducible Emax 41.21 % 10.1021/np100874f
Mus musculus Nitric oxide synthase, inducible Emax 43.72 % 10.1021/np200279r
Mus musculus Nitric oxide synthase, inducible IC50 500.0 nM 10.1021/jm00049a007
Mus musculus Nitric oxide synthase, inducible IC50 10000.0 nM 10.1016/0960-894X(96)00144-8
Mus musculus Nitric oxide synthase, inducible IC50 14000.0 nM 10.1021/jm980073h
Mus musculus Nitric oxide synthase, inducible IC50 14740.0 nM 10.1016/j.bmc.2007.04.030
Mus musculus Nitric oxide synthase, inducible IC50 27550.0 nM 10.1016/j.bmc.2020.115733
Mus musculus Nitric oxide synthase, inducible IC50 80000.0 nM 10.1016/j.bmcl.2003.11.010
Mus musculus Nitric oxide synthase, inducible IC50 143550.0 nM 10.1021/np100874f
Mus musculus Nitric oxide synthase, inducible IC50 152460.0 nM 10.1021/np200279r
Mus musculus Nitric oxide synthase, inducible Ki 570.0 nM 10.1021/jm100947x
Mus musculus Nitric oxide synthase, inducible Ki 4280.0 nM 10.1021/jm061305c
Mus musculus RAW264.7 Activity 101.7 % 10.1021/acs.jnatprod.6b00407
Mus musculus RAW264.7 CC50 100000.0 nM 10.1021/np100874f
Mus musculus RAW264.7 Emax 42.1 % 10.1021/acs.jnatprod.6b00407
Mus musculus RAW264.7 IC50 2918.0 nM 10.1016/j.bmc.2020.115733
Mus musculus RAW264.7 IC50 37700.0 nM 10.1021/acs.jnatprod.6b00730
Mus musculus RAW264.7 IC50 39500.0 nM 10.1016/j.bmc.2020.115971
Mus musculus RAW264.7 IC50 43600.0 nM 10.1021/np900320e
Mus musculus RAW264.7 IC50 144300.0 nM 10.1021/acs.jnatprod.6b00407
Mus musculus RAW264.7 IC50 146400.0 nM 10.1021/np400523k
Mus musculus RAW264.7 Inhibition 2.53 % 10.1021/np900320e
Plasmodium falciparum Plasmodium falciparum Potency 10417.9 nM None
Rattus norvegicus Nitric-oxide synthase, brain Activity 2.0 % 10.1016/j.ejmech.2008.12.007
Rattus norvegicus Nitric-oxide synthase, brain IC50 600.0 nM 10.1016/0960-894X(96)00144-8
Rattus norvegicus Nitric-oxide synthase, brain IC50 600.0 nM 10.1021/jm980073h
Rattus norvegicus Nitric-oxide synthase, brain IC50 4000.0 nM 10.1021/jm900380j
Rattus norvegicus Nitric-oxide synthase, brain IC50 5000.0 nM 10.1016/j.bmc.2012.01.037
Rattus norvegicus Nitric-oxide synthase, brain IC50 6000.0 nM 10.1021/jm900380j
Rattus norvegicus Nitric-oxide synthase, brain Ki 4550.0 nM 10.1021/jm100947x
Rattus norvegicus Nitric-oxide synthase, brain Ratio IC50 1.0 None 10.1016/j.bmc.2012.01.037
Rattus norvegicus Nitric oxide synthase, inducible IC50 20000.0 nM 10.1021/jm00049a007
Rattus norvegicus Rattus norvegicus EC50 1100.0 nM 10.1016/s0960-894x(99)00411-4
Rattus norvegicus Rattus norvegicus EC50 3000.0 nM 10.1021/jm980073h
Rattus norvegicus Rattus norvegicus Emax 69.0 % 10.1016/s0960-894x(99)00411-4
Rattus norvegicus Rattus norvegicus Emax 138.0 % 10.1021/jm980073h
Rattus norvegicus Rattus norvegicus IC50 200.0 nM 10.1021/jm980073h
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 398.1 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 946.6 nM None
Saccharomyces cerevisiae Saccharomyces cerevisiae Potency 9200.0 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 5.487 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 23.98 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 27.97 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.53 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.19 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.05 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.48 % 10.6019/CHEMBL4495565
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Ki 15.0 nM 10.1021/jm3015926
None Unchecked Ki 610.0 nM 10.1021/jm061305c
None Unchecked Ks 1.32 uM 10.1021/jm501723p
None Unchecked Ks 4.4 uM 10.1021/jm501723p
None Unchecked Ks nan None 10.1021/jm501723p
None Unchecked Potency 3162.3 nM None
None Unchecked Potency 12589.3 nM None
None Unchecked Ratio 1.3 None 10.1021/jm100947x
None Unchecked Ratio 8.0 None 10.1021/jm100947x
None Unchecked Ratio IC50 0.7 None 10.1021/jm900380j
None Unchecked Ratio Ki 1.2 None 10.1021/jm061305c
None Unchecked Ratio Ki 7.0 None 10.1021/jm061305c
None Unchecked Ratio Ki 11.0 None 10.1021/jm3015926
None Unchecked Ratio Ki 293.0 None 10.1021/jm3015926
None Unchecked Selectivity 0.0063 None 10.1016/j.bmcl.2003.11.010
None Unchecked Selectivity 0.01 None 10.1021/jm990111c
None Unchecked Selectivity 0.025 None 10.1021/jm00049a007
None Unchecked Selectivity 2.5 None 10.1021/jm990111c

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013738 C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)O>>N=C(NCCC[C@H](N)C(=O)O)N[N+](=O)[O-] enzymemap_67854
AKRT016271 N=C(NCCC[C@H](N)C(=O)Nc1ccc2c(CC(N)=O)cc(=O)oc2c1)N[N+](=O)[O-]>>N=C(NCCC[C@H](N)C(=O)O)N[N+](=O)[O-] enzymemap_65326