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D-histidinium(2+)

AlkaPlorer ID: AK004105

Synonym: 'histidina', 'D-Histidine', 'L-histidinium(1+)', 'L-histidine monocation', 'L-histidine', 'L-histidine anion', 'D-histidinium(2+)', 'L-histidine dianion', 'Histidine', '71-00-1', 'D-histidinate(2-)', '(2S)-2-amino-3-(1H-imidazol-4-yl)propanoate', 'L-Histidine', 'D-histidine', 'D-histidine monoanion', 'L-(-)-histidine', 'D-HISTIDINE', 'alpha-Amino-1H-imidazole-4-propionic acid', '4-(2S)-2-ammonio-2-carboxyethyl-1H-imidazol-3-ium', 'DL-Histidine', 'D-histidine monocation', 'L-His', 'D-Histidin', '(R)-alpha-Amino-1H-imidazole-4-propionic acid', 'L-histidinate(1-)', 'DHI', 'L-histidine dication', 'L-histidinium(2+)', 'H', 'L-Histidin', 'D-histidinium(1+)', 'L-histidine monoanion', '(2S)-2-ammonio-3-(1H-imidazol-3-ium-4-yl)propanoate', 'D-histidinate(1-)', '4-(2R)-2-ammonio-2-carboxyethyl-1H-imidazol-3-ium', 'Histidin', '(2S)-2-amino-3-imidazol-1-id-4-ylpropanoate', '(2R)-2-ammonio-3-(1H-imidazol-3-ium-4-yl)propanoate', 'D-histidine dication', 'D-histidine dianion', '(S)-alpha-Amino-1H-imidazole-4-propionic acid', '(S)-alpha-amino-1H-Imidazole-4-propanoic acid', 'His', 'HISTIDINE', '(2R)-2-amino-3-imidazol-1-id-4-ylpropanoate', '(S)-4-(2-Amino-2-carboxyethyl)imidazole', '(2R)-2-amino-3-(1H-imidazol-4-yl)propanoate', 'L-histidinate(2-)', 'histidine'

IUPAC Name: (2R)-2-amino-3-(1H-imidazol-5-yl)propanoic acid

Structure

SMILES: N[C@H](CC1=CNC=N1)C(=O)O

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InChI: InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m1/s1

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InChIKey: HNDVDQJCIGZPNO-RXMQYKEDSA-N

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Reference

PubChem CID: 71083

CAS: 351-50-8

NPASS: NPC326518

Properties Information

Molecule Weight: 155.15699999999998

TPSA？: 92.0

MolLogP？: -0.6359000000000001

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Carbonic anhydrase KA 19.5 uM 10.1016/j.bmc.2009.12.058
Candida glabrata CBS 138 Carbonic anhydrase Ka 21.2 uM 10.1016/j.bmcl.2010.01.054
Cryptococcus neoformans var. grubii Carbonic anhydrase 2 KA 47.2 uM 10.1016/j.bmc.2009.12.058
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 14125.4 nM None
Homo sapiens Carbonic anhydrase I Ka 0.09 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase I Ka 0.09 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmc.2018.07.011
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2006.05.023
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2012.08.088
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2012.12.009
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.bmcl.2016.11.027
Homo sapiens Carbonic anhydrase I KA 0.09 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase I Kcat 9.1 10'5/s 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase II Ka 43.0 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase II Ka 43.0 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase II Ka 43.0 uM 10.1016/j.bmcl.2009.01.105
Homo sapiens Carbonic anhydrase II Ka 43.0 uM 10.1016/j.bmcl.2010.01.054
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmc.2018.07.011
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2006.05.023
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2012.08.088
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2012.12.009
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.bmcl.2016.11.027
Homo sapiens Carbonic anhydrase II KA 43.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase II Kcat 2.7 10'6/s 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase III Ka 1.12 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase III KA 1.1 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase III KA 1.12 uM 10.1016/j.bmcl.2008.10.005
Homo sapiens Carbonic anhydrase III Kcat 16.9 10'4/s 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase IV Ka 12.3 uM 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase IV KA 12.3 uM 10.1016/j.bmcl.2009.05.026
Homo sapiens Carbonic anhydrase IV KA 12.3 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase IV Kcat 3.8 10'6/s 10.1016/j.bmcl.2008.06.075
Homo sapiens Carbonic anhydrase IV Kcat 3.8 10'6/s 10.1016/j.bmcl.2009.05.026
Homo sapiens Carbonic anhydrase IX KA 12.5 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase IX KA 12.5 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VA KA 0.12 uM 10.1016/j.bmcl.2006.11.075
Homo sapiens Carbonic anhydrase VA KA 0.12 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VB KA 4.38 uM 10.1016/j.bmcl.2006.11.075
Homo sapiens Carbonic anhydrase VB KA 4.4 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VI Ka 13.0 uM 10.1016/j.bmc.2007.03.004
Homo sapiens Carbonic anhydrase VI KA 13.0 uM 10.1016/j.bmc.2010.01.059
Homo sapiens Carbonic anhydrase VI KA 13.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase VII KA 0.71 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase VII KA 0.71 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase XII KA 24.7 uM 10.1016/j.bmc.2008.02.021
Homo sapiens Carbonic anhydrase XII KA 25.0 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase XIII KA 0.09 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Carbonic anhydrase XIV KA 2.37 uM 10.1016/j.bmcl.2007.05.052
Homo sapiens Carbonic anhydrase XIV KA 2.4 uM 10.1016/j.ejmech.2021.113875
Homo sapiens Histone deacetylase 6 Inhibition -48.73 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 5.27 % 10.6019/CHEMBL4808148
Homo sapiens L-type amino acid transporter 1 Activity 78.0 % 10.1021/acs.jmedchem.8b01007
Homo sapiens L-type amino acid transporter 1 IC50 460000.0 nM 10.1021/acs.jmedchem.8b01007
Homo sapiens L-type amino acid transporter 1 Inhibition 33.0 % 10.1021/acs.jmedchem.8b01007
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Methanobacterium thermoautotrophicum Carbonic anhydrase Ka 57.0 uM 10.1016/j.bmcl.2010.01.054
Methanosarcina thermophila Carbonic anhydrase KA 46.0 uM 10.1016/j.bmcl.2016.11.027
Mus musculus Carbonic anhydrase 15 KA 14.1 uM 10.1016/j.bmcl.2009.05.026
Mus musculus Carbonic anhydrase 15 Kcat 15.0 10'5/s 10.1016/j.bmcl.2009.05.026
Mus musculus Carbonic anhydrase XIII KA 0.09 uM 10.1016/j.bmcl.2006.05.023
Saccharomyces cerevisiae S288c Carbonic anhydrase Ka 85.0 uM 10.1016/j.bmcl.2009.01.105
Saccharomyces cerevisiae S288c Carbonic anhydrase Ka 85.0 uM 10.1016/j.bmcl.2010.01.054
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 11.9 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.7 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 5.32 % 10.21203/rs.3.rs-23951/v1
Trypanosoma cruzi (strain CL Brener) Carbonic anhydrase-like protein, putative KA 7.54 uM 10.1016/j.bmc.2018.07.011
None Hairpin ribozyme RNA K obs 0.0085 None 10.1016/s0960-894x(01)00608-4
None Hairpin ribozyme RNA K obs 0.026 None 10.1016/s0960-894x(01)00608-4
None Unchecked Ka 57.0 uM 10.1016/j.bmcl.2009.01.105
None Unchecked KA 0.012 uM 10.1016/j.bmcl.2012.08.088
None Unchecked KA 0.012 uM 10.1016/j.bmcl.2012.12.009
None Unchecked KA 0.086 uM 10.1016/j.bmcl.2016.11.027
None Unchecked KA 0.09 uM 10.1016/j.bmcl.2012.12.009
None Unchecked KA 4.13 uM 10.1016/j.bmc.2018.07.011
None Unchecked KA 18.1 uM 10.1016/j.bmcl.2016.01.078
None Unchecked KA 26.0 uM 10.1016/j.bmc.2010.01.059
None Unchecked KA 46.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked KA 57.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked KA 73.0 uM 10.1016/j.bmcl.2008.10.005
None Unchecked Kcat 2.16 10'6/s 10.1016/j.bmcl.2016.11.027

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT002148 CC(=O)C(=O)O.N[C@H](Cc1c[nH]cn1)C(=O)O>>C[C@@H](N)C(=O)O.O=C(O)C(=O)Cc1c[nH]cn1 None
AKRT002149 CC(=O)C(=O)O.N[C@H](Cc1c[nH]cn1)C(=O)O>>O=C(O)C(=O)Cc1c[nH]cn1 enzymemap_41826
AKRT002152 CC(=O)C(=O)O.N[C@H](Cc1cnc[nH]1)C(=O)O>>C[C@@H](N)C(=O)O.O=C(O)C(=O)Cc1cnc[nH]1 None
AKRT002153 CC(=O)C(=O)O.N[C@H](Cc1cnc[nH]1)C(=O)O>>O=C(O)C(=O)Cc1cnc[nH]1 enzymemap_41826
AKRT004716 CC(=O)[CoA].N[C@H](Cc1cnc[nH]1)C(=O)O>>CC(=O)N[C@H](Cc1cnc[nH]1)C(=O)O enzymemap_30751
AKRT012658 C[33S].N[C@H](Cc1cnc[nH]1)C(=O)O>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@@H](CCN[C@H](Cc1cnc[nH]1)C(=O)O)C(=O)O None
AKRT014507 C[S+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@H](Cc1c[nH]cn1)C(=O)O>>N[C@@H](CCN[C@H](Cc1c[nH]cn1)C(=O)O)C(=O)O R12341
AKRT014529 C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@H](Cc1c[nH]cn1)C(=O)O>>N[C@@H](CCN[C@H](Cc1c[nH]cn1)C(=O)O)C(=O)O RXN-19817
AKRT014692 C[SAH].N[C@H](Cc1cnc[nH]1)C(=O)O>>N[C@@H](CCN[C@H](Cc1cnc[nH]1)C(=O)O)C(=O)O enzymemap_40103
AKRT019840 N[C@@H](Cc1c[nH]cn1)C(=O)O>>N[C@H](Cc1c[nH]cn1)C(=O)O RXN-19818
AKRT020139 N[C@@H](Cc1cnc[nH]1)C(=O)O>>N[C@H](Cc1cnc[nH]1)C(=O)O None
AKRT020340 N[C@H](Cc1c[nH]cn1)C(=O)O>>C[C@@H](N)C(=O)O enzymemap_41826
AKRT020341 N[C@H](Cc1c[nH]cn1)C(=O)O>>N[C@@H](Cc1c[nH]cn1)C(=O)O R12313
AKRT020342 N[C@H](Cc1c[nH]cn1)C(=O)O>>N[C@H](Cc1cnc[nH]1)C(=O)O enzymemap_86996
AKRT020343 N[C@H](Cc1c[nH]cn1)C(=O)O>>O=C(O)C(=O)Cc1c[nH]cn1 enzymemap_21925
AKRT020376 N[C@H](Cc1cnc[nH]1)C(=O)O.N[C@H](Cc1cnc[nH]1)C(=O)O>>N[C@H](Cc1cnc[nH]1)C(=O)N[C@H](Cc1cnc[nH]1)C(=O)O enzymemap_90695
AKRT020377 N[C@H](Cc1cnc[nH]1)C(=O)O>>C[C@@H](N)C(=O)O enzymemap_41826
AKRT020378 N[C@H](Cc1cnc[nH]1)C(=O)O>>N[C@@H](Cc1cnc[nH]1)C(=O)O None
AKRT020379 N[C@H](Cc1cnc[nH]1)C(=O)O>>N[C@H](Cc1c[nH]cn1)C(=O)O enzymemap_86996
AKRT020380 N[C@H](Cc1cnc[nH]1)C(=O)O>>O=C(O)C(=O)Cc1cnc[nH]1 enzymemap_21920