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Dihydrofolic Acid

AlkaPlorer ID: AK022036

Synonym: None

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

Structure

SMILES: NC1=NC2=C(N=C(CNC3=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C3)CN2)C(=O)N1

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InChI: InChI=1S/C19H21N7O6/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/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

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InChIKey: OZRNSSUDZOLUSN-LBPRGKRZSA-N

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Reference

PubChem CID: 135398604

CAS: 4033-27-6

LOTUS: LTS0104498

NPASS: NPC248862

Properties Information

Molecule Weight: 443.4200000000001

TPSA？: 211.89

MolLogP？: 0.0099999999999996

Number of H-Donors: 7

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli Dihydrofolate reductase Kd 210.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 220.0 nM 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Kd 240.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 243.0 nM 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Kd 2000.0 nM 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Kd 2400.0 nM 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase Kd 2600.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 2900.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 6200.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase Kd 6600.0 nM 10.1021/jm00396a019
Escherichia coli Dihydrofolate reductase k_off 22.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 28.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 56.0 s-1 10.1021/jm00093a026
Escherichia coli Dihydrofolate reductase k_off 76.0 s-1 10.1021/jm00093a026
Escherichia coli (strain K12) Bifunctional protein FolC Inhibition nan % 10.1038/nchembio.108
Escherichia coli (strain K12) Bifunctional protein FolC Ki 3100.0 nM 10.1038/nchembio.108
Homo sapiens Homo sapiens Kd 1.4 None 10.1021/jm950793d
Homo sapiens Homo sapiens Kd 5.0 None 10.1021/jm950793d
Homo sapiens Homo sapiens Kd 50.0 None 10.1021/jm950793d
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 integrase Inhibition 50.0 % 10.1021/jm990322h
Lactobacillus casei Dihydrofolate reductase deltaOD 0.032 /min 10.1021/jm00221a038
Lactobacillus casei Dihydrofolate reductase Km 360.0 nM 10.1021/jm00221a038
Lactobacillus casei Thymidylate synthase deltaOD 0.02 /min 10.1021/jm00221a038
Lactobacillus casei Thymidylate synthase Inhibition 26.0 % 10.1021/jm00221a038
Mus musculus Mus musculus Kd 0.2 None 10.1021/jm950793d
Mus musculus Mus musculus Kd 0.81 None 10.1021/jm950793d
Plasmodium falciparum K1 Dihydrofolate reductase Kd nan None 10.1021/jm00093a026
None Unchecked Kd 1.3 None 10.1021/jm950793d
None Unchecked Kd nan None 10.1021/jm950793d

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT015114 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.N=c1[nH]c2c(c(=O)[nH]1)N=C(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)CC1CN2 enzymemap_27430
AKRT015115 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.N=c1[nH]c2c(c(=O)[nH]1)N=C(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_27449
AKRT015116 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2 R02101
AKRT015117 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(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)CC1CN2 enzymemap_27430
AKRT015118 Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.Nc1nc2c(c(=O)[nH]1)N=C(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_27449
AKRT016697 N=c1[nH]c2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_27427
AKRT016701 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=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_27424
AKRT016703 N=c1[nH]c2c(c(=O)[nH]1)N=C(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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28034
AKRT016704 N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=CO>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_91195
AKRT016705 N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)O)cc1)CN2 enzymemap_67563
AKRT016706 N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>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 enzymemap_23035
AKRT016707 N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N[C@@H](CCC(=O)O)C(=O)O enzymemap_67563
AKRT016742 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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_23036
AKRT017324 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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28034
AKRT017327 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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_28034
AKRT019078 N[C@@H](CCC(=O)O)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)cc1)CN2 enzymemap_90450
AKRT019079 N[C@@H](CCC(=O)O)C(=O)O.N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)O)cc1)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_90313
AKRT019090 N[C@@H](CCC(=O)O)C(=O)O.N[C@@H](CCC(=O)O)C(=O)O.N[C@@H](CCC(=O)O)C(=O)O.N[C@@H](CCC(=O)O)C(=O)O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>[NH-]c1nc(O)c2c(n1)NCC(CNc1ccc(C(=O)N(C(=O)CCC(N)C(=O)O)[C@@](C(=O)CCC(N)C(=O)O)(C(=O)OC(=O)CCC(N)C(=O)O)C(CC(=O)O)C(=O)CCC(N)C(=O)O)cc1)=N2 MNXR100120
AKRT019120 N[C@@H](CCC(=O)O)C(=O)O.Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 DIHYDROFOLATESYNTH-RXN
AKRT020597 Nc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.N=c1[nH]c2c(c(=O)[nH]1)N=C(COP(=O)(O)OP(=O)(O)O)CN2>>N=c1[nH]c2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_40074
AKRT020598 Nc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1.Nc1nc2c(c(=O)[nH]1)N=C(COP(=O)(O)OP(=O)(O)O)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_40074
AKRT021135 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 R02101
AKRT021140 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)CC1CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_27427
AKRT021148 Nc1nc2c(c(=O)[nH]1)N1CN(c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)C[C@H]1CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_27424
AKRT021155 Nc1nc2c(c(=O)[nH]1)N=C(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 59144
AKRT021157 Nc1nc2c(c(=O)[nH]1)N=C(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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)cc1)CN2 enzymemap_90450
AKRT021158 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2.O=CO>>Nc1nc2c(c(=O)[nH]1)N=C(CN(C=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_91195
AKRT021159 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>N[C@@H](CCC(=O)O)C(=O)O enzymemap_67563
AKRT021160 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 MNXR144479
AKRT021161 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)O)cc1)CN2 enzymemap_67563
AKRT021162 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N=C(COP(=O)(O)OP(=O)(O)O)CN2 MNXR144479
AKRT021163 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2>>Nc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 RXN-19329
AKRT021164 Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)O)cc1)CN2.N[C@@H](CCC(=O)O)C(=O)O>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_90313
AKRT021234 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)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 enzymemap_23036
AKRT021605 Nc1nc2ncc(CNc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)nc2c(=O)[nH]1>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 RXN-22709
AKRT024961 [NH-]c1nc(O)c2c(n1)NCC(CNc1ccc(C(=O)N(C(=O)CCC(N)C(=O)O)[C@@](C(=O)CCC(N)C(=O)O)(C(=O)OC(=O)CCC(N)C(=O)O)C(CC(=O)O)C(=O)CCC(N)C(=O)O)cc1)=N2>>Nc1nc2c(c(=O)[nH]1)N=C(CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2 MNXR157463