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(6S)-5,6,7,8-tetrahydrofolate(2-)

AlkaPlorer ID: AK012450

Synonym: '', 'Tetrahydrofolic acid', '5,6,7,8-tetrahydrofolic acid', '(6S)-Tetrahydrofolic acid', '(6S)-5,6,7,8-tetrahydrofolate dianion', 'tetrahydrofolic acid', 'THFA', 'Tetrahydrofolate', 'tetrahydrofolate', '(6S)-Tetrahydrofolate', 'THF', '5,6,7,8-Tetrahydrofolate', '(6S)-THFA', '(6S)-5,6,7,8-tetrahydrofolate'

IUPAC Name: (2S)-2-[[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

Structure

SMILES: N=C1N=C(O)C2=C(NCC(CNC3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C3)N2)N1

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InChI: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

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InChIKey: MSTNYGQPCMXVAQ-KIYNQFGBSA-N

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Reference

PubChem CID: 135444742

CAS: 135-16-0

NPASS: NPC328611

Properties Information

Molecule Weight: 445.43600000000015

TPSA？: 212.54999999999995

MolLogP？: -0.0393299999999993

Number of H-Donors: 9

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli Dihydrofolate reductase Kd 60.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 300.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase k_off 1.4 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 3.6 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 12.2 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 14.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 2.4 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 10.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 12.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 13.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 18.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer 52.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Rate of hydride transfer nan None 10.1021/jm00093a026
Homo sapiens Folylpoly-gamma-glutamate synthetase Km 4200.0 nM 10.1021/jm00113a011
Homo sapiens Folylpoly-gamma-glutamate synthetase Vmax 135.0 % 10.1021/jm00113a011
Homo sapiens Histone deacetylase 6 Inhibition -7.59 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -3.39 % 10.6019/CHEMBL4808148
Mus musculus Folylpoly-gamma-glutamate synthetase Km 8000.0 nM 10.1021/jm00123a037
Mus musculus Folylpoly-gamma-glutamate synthetase Km 7100000000.0 nM 10.1021/jm00145a012
Mus musculus Folylpoly-gamma-glutamate synthetase Relative Km 0.051 None 10.1021/jm00145a012
Mus musculus Folylpoly-gamma-glutamate synthetase Relative Vmax 1.31 None 10.1021/jm00145a012
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -8.449 % 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 0.03 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 28.84 % 10.21203/rs.3.rs-23951/v1
None Unchecked Ratio 32.1 None 10.1021/jm00113a011

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT016320 N=CN1c2c([nH]c(=N)[nH]c2=O)NCC1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1>>N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28060
AKRT016728 N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_23303
AKRT016729 N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=C=O None
AKRT016730 N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=CO None
AKRT016731 N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.N=CN[C@@H](CCC(=O)O)C(=O)O>>N=CN1c2c([nH]c(=N)[nH]c2=O)NCC1CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 enzymemap_28060
AKRT016732 N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1NC=O>>N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1N None
AKRT016733 N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=CO>>N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_91250
AKRT017325 NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1NC=O.N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28028
AKRT017328 NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1NC=O.Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1N.Nc1nc2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 None
AKRT017329 NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1NC=O.Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28028
AKRT019081 N[C@@H](CCC(=O)O)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)cc1)CN2 enzymemap_90383
AKRT021205 Nc1nc2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_23303
AKRT021206 Nc1nc2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=C=O None
AKRT021207 Nc1nc2c(c(=O)[nH]1)NC(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=CO None
AKRT021211 Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.N[C@@H](CCC(=O)O)C(=O)O>>Nc1nc2c(c(=O)[nH]1)NC(CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)cc1)CN2 enzymemap_90383