UCSF

ZINC00057464

Substance Information

In ZINC since Heavy atoms Benign functionality
July 23rd, 2004 17 Yes

CAS Numbers: 58-14-0 , [58-14-0]

Other Names:

2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine

2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine; 2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine; 2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine; 2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-; 2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-; 4753

2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine; 2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine; 2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine; 5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine; 5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine; 5-(4-Chl

2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine

5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamine

5-(4-Chlorophenyl)-6-ethylpyrimidine-2,4-diamine

58-14-0; C07391; Pyrimethamine

58-14-0; CPD000058714; Pyrimethamine; SAM002554921

58-14-0; D00488; Daraprim (TN); Pyrimethamine (JAN/USP/INN)

58-14-0; Prestwick_504; Pyrimethamine

BAN

BRD-K88429204-001-05-4

BRD-K88429204-001-21-1

CD

CD;Chloridin;Chloridine;Chloridyn;Diaminopyritamin;Ethylpyrimidine;Pirimetamin;Pirimetamina;Primethamine;Pyremethamine;Pyrimethamin

Chloridin

Chloridine

Chloridyn

CPD0-1583; pyrimethamine

CPD000058714; Pyrimethamine; SAM002554921

DAP001493

Darachlor

Daraclor

Darapram

Daraprim

Daraprime

Diaminopyritamin

Disulone

Erbaprelina

Ethylpyrimidine

EXR-101

Fansidar

FDA

GNF-PF-5586

GNF-Pf-5586; TCMDC-123831; TCMDC-125860

INN

JAN

Khloridin

Malacid

Malacide

Malocid

Malocide

Maloprim

MCB-3837

MFCD00057350

N/A

NA

NSC 3061

Oxaquin

Pirimecidan

Pirimetamin

Pirimetamina

pirimetamina; pyrimethamine; pyrimethaminum

Pirimetmin

Primethamine

Pyremethamine

Pyrimethamin

Pyrimethamine (BAN

Pyrimethamine (FDA

Pyrimethamine Hcl

RP 4753

TCMDC-123831

TCMDC-125860

Tindurin

Tinduring

USP)

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 2.84 6.53 -28.58 5 4 1 79 249.725 2
Mid Mid (pH 6-8) 2.84 6.08 -5.33 4 4 0 78 248.717 2

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 1.79e-01 g/l DrugBank-approved
Melting Pt.: 233-2340C Toronto Research Chemicals
Purity 97% APIChem
Therapy antimalarial SMDC Pharmakon
Indications antimalerial KeyOrganics Bioactives
Solubility: DMSO, Ethanol (hot) Toronto Research Chemicals
UniProt Database Links DRTS_PLAFK; DRTS_PLAVI ChEBI
Secondary Category Multidrug Transporters Tocris
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : P-4000; NCC_SUPPLIER_SAMPLE_COMMENTS : OFF-WHITE POWDER NIH Clinical Collection via PubChem
Target NULL Selleck Chemicals
Biological Description Potent inhibitor of multi-drug and toxin extrusion (MATE) transporters (Ki values are 46 and 77 nM for human MATE2-K-HEK293 and MATE1-HEK293 cells respectively). Also inhibits dihydrofolate reductase (DHFR). Tocris
Primary Action Potent inhibitor of multi-drug and toxin extrusion (MATE) transporters; also inhibits DHFR Tocris
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: P-4000; SUPPLIER_COMMENTS: OFF-WHITE POWDER NIH Clinical Collection via PubChem
Solubility Soluble to 100 mM in DMSO and to 10 mM in ethanol Tocris
Primary Category Transporters Tocris

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
DRTS-1-E Bifunctional Dihydrofolate Reductase-thymidylate Synthase (cluster #1 Of 3), Eukaryotic Eukaryotes 80 0.58 Binding ≤ 10μM
DYR-1-E Dihydrofolate Reductase (cluster #1 Of 3), Eukaryotic Eukaryotes 2300 0.46 Binding ≤ 10μM
DRTS-1-E Dihydrofolate Reductase (cluster #1 Of 1), Eukaryotic Eukaryotes 80 0.58 Functional ≤ 10μM
DYR-1-F Dihydrofolate Reductase (cluster #1 Of 1), Fungal Fungi 10 0.66 Binding ≤ 10μM
Z50339-1-O Pneumocystis Carinii (cluster #1 Of 2), Other Other 0 0.00 Functional ≤ 10μM
Z50418-5-O Trypanosoma Brucei (cluster #5 Of 6), Other Other 7000 0.42 Functional ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 80 0.58 Functional ≤ 10μM
Z50426-1-O Plasmodium Falciparum (isolate K1 / Thailand) (cluster #1 Of 9), Other Other 9900 0.41 Functional ≤ 10μM
Z50472-1-O Toxoplasma Gondii (cluster #1 Of 4), Other Other 700 0.51 Functional ≤ 10μM
Z80186-3-O K562 (Erythroleukemia Cells) (cluster #3 Of 3), Other Other 5000 0.44 ADME/T ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
DRTS_TOXGO Q07422 Dihydrofolate Reductase, Toxgo 390 0.53 Binding ≤ 1μM
DYR_PNECA P16184 Dihydrofolate Reductase, Pneca 9.7 0.66 Binding ≤ 1μM
DRTS_PLAFK P13922 Dihydrofolate Reductase, Plafk 0.19 0.80 Binding ≤ 1μM
DYR_HUMAN P00374 Dihydrofolate Reductase, Human 1.2 0.73 Binding ≤ 1μM
DYR_PNECA P16184 Dihydrofolate Reductase, Pneca 2800 0.46 Binding ≤ 10μM
DRTS_PLAFK P13922 Dihydrofolate Reductase, Plafk 0.19 0.80 Binding ≤ 10μM
DYR_HUMAN P00374 Dihydrofolate Reductase, Human 1.2 0.73 Binding ≤ 10μM
DYR_RAT Q920D2 Dihydrofolate Reductase, Rat 1500 0.48 Binding ≤ 10μM
DRTS_TOXGO Q07422 Dihydrofolate Reductase, Toxgo 390 0.53 Binding ≤ 10μM
DRTS_PLAFK P13922 Dihydrofolate Reductase, Plafk 80 0.58 Functional ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 1.2 0.73 Functional ≤ 10μM
Z50426 Z50426 Plasmodium Falciparum (isolate K1 / Thailand) 9900 0.41 Functional ≤ 10μM
Z50339 Z50339 Pneumocystis Carinii 0.1 0.82 Functional ≤ 10μM
Z50472 Z50472 Toxoplasma Gondii 0.1 0.82 Functional ≤ 10μM
Z50418 Z50418 Trypanosoma Brucei 7000 0.42 Functional ≤ 10μM
Z80186 Z80186 K562 (Erythroleukemia Cells) 5000 0.44 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
E2F mediated regulation of DNA replication
G1/S-Specific Transcription
Metabolism of folate and pterines
Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation

Analogs ( Draw Identity 99% 90% 80% 70% )

No pre-computed analogs available. Try a structural similarity search.