Navigation

name Structure Reference Source Properties Activities Metabolism

D-serine

AlkaPlorer ID: AK007274

Synonym: '', 'L-Serin', '(2S)-2-amino-3-hydroxypropanoic acid', 'Ser', 'serine', '(2R)-2-amino-3-hydroxypropanoic acid', 'Serine', '(S)-alpha-Amino-beta-hydroxypropionic acid', 'L-3-Hydroxy-2-aminopropionic acid', '(S)-2-amino-3-hydroxypropanoic acid', '(R)-2-amino-3-hydroxypropanoic acid', 'S', 'SERINE', 'beta-Hydroxyalanine', 'DSN', '2-Amino-3-hydroxypropionic acid', 'Serin', 'D-Serine', '2-amino-3-hydroxypropanoic acid', '3-Hydroxyalanine', '(S)-(-)-serine', 'L-3-Hydroxy-alanine', '(R)-2-Amino-3-hydroxy-propionic acid', 'D-Serin', 'L-serine', 'D-SERINE', 'L-(-)-serine', 'L-2-Amino-3-hydroxypropionic acid', 'L-Serine', 'L-Ser', '(S)-serine', 'beta-Hydroxy-L-alanine'

IUPAC Name: (2R)-2-amino-3-hydroxypropanoic acid

Structure

SMILES: N[C@H](CO)C(=O)O

copy

InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1

copy

InChIKey: MTCFGRXMJLQNBG-UWTATZPHSA-N

copy

Properties Information

Molecule Weight: 105.093

TPSA？: 83.55

MolLogP？: -1.6093999999999995

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Bloom syndrome protein Potency 2.5 nM None
Homo sapiens HERG Potency 35481.3 nM None
Homo sapiens Histone deacetylase 6 Inhibition -16.26 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -7.83 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 22.4 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 11917.3 nM None
Homo sapiens Neutral amino acid transporter A IC50 3937000.0 nM None
Homo sapiens Neutral amino acid transporter B(0) IC50 4913000.0 nM None
Homo sapiens Prelamin-A/C Potency 12589.3 nM None
Homo sapiens Proton-coupled amino acid transporter 1 Ki 22000000.0 nM 10.1016/j.bmc.2011.08.058
Homo sapiens Proton-coupled amino acid transporter 1 pKi -1.34 mM 10.1016/j.bmc.2011.08.058
Homo sapiens Regulator of G-protein signaling 4 Potency 843.7 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 2985.5 nM None
Mus musculus Cerebellum Drug uptake nan None 10.1124/dmd.112.046482
Mus musculus Cortex Drug uptake nan None 10.1124/dmd.112.046482
Mus musculus Mus musculus AUC 40648.0 ng.hr.mL-1 10.1124/dmd.112.046482
Mus musculus Mus musculus AUC 46023.0 ng.hr.mL-1 10.1124/dmd.112.046482
Mus musculus Mus musculus AUC 65778.0 ng.hr.mL-1 10.1124/dmd.112.046482
Mus musculus Mus musculus AUC 80899.0 ng.hr.mL-1 10.1124/dmd.112.046482
Mus musculus Mus musculus AUC 95768.0 ng.hr.mL-1 10.1124/dmd.112.046482
Mus musculus Mus musculus Cmax 186601.96 nM 10.1124/dmd.112.046482
Mus musculus Mus musculus Cmax 231040.06 nM 10.1124/dmd.112.046482
Mus musculus Mus musculus Cmax 264440.0 nM 10.1124/dmd.112.046482
Mus musculus Mus musculus T1/2 1.2 hr 10.1124/dmd.112.046482
Mus musculus Mus musculus T1/2 1.5 hr 10.1124/dmd.112.046482
Mus musculus Mus musculus T1/2 10.0 hr 10.1124/dmd.112.046482
Mus musculus Mus musculus Tmax 0.7 hr 10.1124/dmd.112.046482
Mus musculus Mus musculus Tmax 1.0 hr 10.1124/dmd.112.046482
Mus musculus Mus musculus Tmax 2.7 hr 10.1124/dmd.112.046482
Rattus norvegicus Amino acid transporter IC50 1581000.0 nM None
Rattus norvegicus Amino acid transporter IC50 2592000.0 nM None
Rattus norvegicus Amino acid transporter Inhibition 25.0 % None
Rattus norvegicus Asc-type amino acid transporter 1 IC50 9400.0 nM None
Rattus norvegicus Glutamate NMDA receptor Activity nan None None
Rattus norvegicus Glutamate NMDA receptor EC50 160.0 nM 10.1016/s0960-894x(99)00194-8
Rattus norvegicus Glutamate NMDA receptor EC50 200.0 nM 10.1021/jm00050a001
Rattus norvegicus Glutamate NMDA receptor IC50 300.0 nM 10.1021/jm00050a001
Rattus norvegicus Glutamate NMDA receptor Ki 316.23 nM 10.1021/jm900363q
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2a EC50 1000.0 nM 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2a Rmax 96.0 % 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2b EC50 620.0 nM 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2b Rmax 93.0 % 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2c EC50 190.0 nM 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate NMDA receptor; Grin1/Grin2c Rmax 100.0 % 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 IC50 670.0 nM 10.1016/s0960-894x(99)00194-8
Rattus norvegicus Ionotropic glutamate receptor NMDA 1/2D EC50 150.0 nM 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Ionotropic glutamate receptor NMDA 1/2D Rmax 111.0 % 10.1021/acs.jmedchem.1c01810
Rattus norvegicus Monocarboxylate transporter 10 Activity nan None 10.1074/jbc.m009462200
Rattus norvegicus Rattus norvegicus Activity nan None None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 354.8 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 12.9 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 26.21 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1472 None 10.1101/2020.04.21.054387
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 -0.1 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.09 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 7.43 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus Activity 83.0 % 10.1016/j.bmcl.2021.128259
Staphylococcus aureus Staphylococcus aureus Activity 85.0 % 10.1016/j.bmcl.2021.128259
Trypanosoma brucei 6-phospho-1-fructokinase Potency 17782.8 nM None
None NON-PROTEIN TARGET Potency 11220.2 nM None
None Unchecked Activity 3.0 uM None
None Unchecked EC50 170.0 nM 10.1021/jm000007r
None Unchecked EC50 210.0 nM 10.1021/jm000007r
None Unchecked EC50 260.0 nM 10.1021/jm000007r
None Unchecked EC50 320.0 nM 10.1021/jm000007r
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked ME 169.0 % 10.1016/s0960-894x(99)00194-8

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT002145 CC(=O)C(=O)O.N[C@H](CO)C(=O)O>>C[C@@H](N)C(=O)O.O=C(O)C(=O)CO None
AKRT002179 CC(=O)C(=O)O>>N[C@H](CO)C(=O)O R00221
AKRT004710 CC(=O)[CoA].N[C@H](CO)C(=O)O>>CC(=O)N[C@H](CO)C(=O)O enzymemap_30758
AKRT005713 CC(C)C[C@H](N)C(=O)N[C@H](CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_66415
AKRT006102 CC(C)C[C@H](NC(=O)[C@H](N)CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_64651
AKRT007195 CCC(=O)[CoA].N[C@H](CO)C(=O)O>>CCC(=O)N[C@H](CO)C(=O)O enzymemap_30768
AKRT011125 COC(=O)[C@H](N)CO>>N[C@H](CO)C(=O)O enzymemap_52962
AKRT012720 C[C@@H](N)C(=O)N[C@H](CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_66500
AKRT012756 C[C@@H](N)C(=O)O.N[C@H](CO)C(=O)O>>C[C@@H](N)C(=O)N[C@H](CO)C(=O)O RXN-11299
AKRT012807 C[C@@H](NC(=O)[C@H](N)CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_66496
AKRT017129 NC(=O)N[C@H](CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_77866
AKRT017216 NC(=O)[C@H](N)CO>>N[C@H](CO)C(=O)O enzymemap_65278
AKRT017397 NC(CO)(CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_28066
AKRT017403 NC(COP(=O)(O)O)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_55969
AKRT017615 NCC(=O)N[C@H](CO)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_66304
AKRT017630 NCC(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2>>N[C@H](CO)C(=O)O enzymemap_27929
AKRT017678 NCC(=O)O.Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2>>N[C@H](CO)C(=O)O MNXR172949
AKRT018284 NCCO.O=C=O>>N[C@H](CO)C(=O)O MNXR195058
AKRT018297 NCCOP(=O)(O)OC(=O)[C@H](N)CO>>N[C@H](CO)C(=O)O enzymemap_57295
AKRT018300 NCCOP(=O)(O)OC[C@@H](N)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_57295
AKRT019518 N[C@@H](CO)C(=O)O>>N[C@H](CO)C(=O)O 5.1.1.18-RXN
AKRT020278 N[C@H](CO)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 enzymemap_27929
AKRT020279 N[C@H](CO)C(=O)O.N[C@@H](CCC(=O)N[C@@H](CS)C(=O)O)C(=O)O>>N[C@@H](CCC(=O)N[C@@H](CS)C(=O)N[C@H](CO)C(=O)O)C(=O)O enzymemap_90611
AKRT020280 N[C@H](CO)C(=O)O.N[C@H](CO)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>N[C@H](CO)C(=O)N[C@H](CO)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT020281 N[C@H](CO)C(=O)O.N[C@H](CO)C(=O)O>>N[C@H](CO)C(=O)N[C@H](CO)C(=O)O enzymemap_90702
AKRT020282 N[C@H](CO)C(=O)O.Nc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 enzymemap_27929
AKRT020283 N[C@H](CO)C(=O)O.O=C(O)CCC(=O)C(=O)O>>N[C@H](CCC(=O)O)C(=O)O.O=C(O)C(=O)CO None
AKRT020284 N[C@H](CO)C(=O)O.O=Cc1cccc([N+](=O)[O-])c1>>N[C@@](CO)(C(=O)O)C(O)c1cccc([N+](=O)[O-])c1 enzymemap_82781
AKRT020285 N[C@H](CO)C(=O)O.O=Cc1ccccc1>>NC(CO)(C(=O)O)C(O)c1ccccc1 enzymemap_82782
AKRT020286 N[C@H](CO)C(=O)O.c1ccc2[nH]ccc2c1>>N[C@H](Cc1c[nH]c2ccccc12)C(=O)O enzymemap_83450
AKRT020287 N[C@H](CO)C(=O)O>>C=C(N)C(=O)O RXN-15581
AKRT020288 N[C@H](CO)C(=O)O>>CC(=O)C(=O)O R00221
AKRT020289 N[C@H](CO)C(=O)O>>C[C@@H](N)C(=O)O enzymemap_41854
AKRT020290 N[C@H](CO)C(=O)O>>NCC(=O)O enzymemap_27929
AKRT020291 N[C@H](CO)C(=O)O>>NCC=O enzymemap_4761
AKRT020292 N[C@H](CO)C(=O)O>>N[C@@H](C=O)C(=O)O 30107
AKRT020293 N[C@H](CO)C(=O)O>>N[C@@H](CO)C(=O)O R00589
AKRT020294 N[C@H](CO)C(=O)O>>N[C@H](C=O)C(=O)O enzymemap_3775
AKRT020295 N[C@H](CO)C(=O)O>>O=C(O)C(=O)CO 37019
AKRT020296 N[C@H](CO)C(=O)O>>O=C=O enzymemap_4761
AKRT020304 N[C@H](COP(=O)(O)O)C(=O)O>>N[C@H](CO)C(=O)O enzymemap_56196
AKRT020321 N[C@H](CS)C(=O)O>>N[C@H](CO)C(=O)O MNXR173315
AKRT022578 O=C(O)C(=O)CO>>N[C@H](CO)C(=O)O enzymemap_21483