General Information of the Compound
Compound ID
CP0053031
Compound Name
4-Aminofolic acid
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Synonyms
(2R)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
4'-Amino-folsaeure
4'-Desoxy-4'-aminofolsaeure
4-Amino pteroylglutamic acid
4-Amino-4-deoxypteroylglutamate
4-Amino-4-desoxy-pteroylglutaminsaeure
4-Amino-PGA
4-Aminofolic acid
4-Aminopteroyl-<R>glutamic acid
4-Aminopteroyl-L-glutamic acid
4-Aminopteroyl-glutamic acid
4-Aminopteroylglutamic acid
A 1784
A-7170;A-Ninopterin
APGA
Aminopteridine
Aminopterin
Aminopterine
Aminopterinum
Aminotrexate
ENT-26079
Kyselina 4-aminolistova
Kyselina 4-aminolistova [Czech]
Kyselina 4-aminopteroylglutamova
Kyselina 4-aminopteroylglutamova [Czech]
Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova
Kyselina N-(p-((2,4-diamino-6-pteridinyl)methyl)benzoyl)-L(+)-glutamova [Czech]
Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova
Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)amino)benzoyl)-L(+)-glutamova [Czech]
L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]
N-(1-((2,4-Diamino-6-pteridinylmethyl)amino)benzoyl)glutaminsaeure
N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid
N-(4-(((2,4-Diamino-6-pteridyl)-methyl)amino)benzoyl)-L-glutamic acid
N-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid
N-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)carbonyl]glutamic acid
Pteramina
Pteramina [Czech]
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Structure
Formula
C19H20N8O5
Molecular Weight
440.42
Canonical SMILES
Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
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InChI
InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
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InChIKey
TVZGACDUOSZQKY-LBPRGKRZSA-N
CAS
54-62-6
Physicochemical Property
logP
0.2441
Rotatable Bonds
9
Heavy Atom Count
32
Polar Areas
219.33
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
10
Complexity
32

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 169371
SID: 14881429
ChEMBL ID
CHEMBL376180
DrugBank ID
DB08878
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01651, Dihydrofolate reductase
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000108 CCRF-CEM Homo sapiens (Human)  1
1
IC50 = 3 nM
   TI
   LI
   LO
   TS
CL000341 WIL2 Homo sapiens (Human)  1
1
IC50 = 25 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 11.8 nM
2 IC50 = 25 nM
3 Ki = 0.21 nM
Protein ID: PT02055, Dihydrofolate reductase
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000266 L1210 Mus musculus (Mouse)  1
1
IC50 = 20 nM
   TI
   LI
   LO
   TS
Protein ID: PT06163, Solute carrier organic anion transporter family member 1A3
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000031 MDCK Canis lupus familiaris (Dog)  1
1
Ki = 500 nM
   TI
   LI
   LO
   TS
Cell Viability or Cytotoxicity Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000266 L1210 Mus musculus (Mouse)  2
1
EC50 = 1.8 nM
   TI
   LI
   LO
   TS
2
IC50 = 3 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Aminopterin )
Drug Name Aminopterin
Company Lederle Laboratories
Indication
leukaemia
Withdrawn from market
Target(s)
Polypeptide deformylase (PDF)
Inhibitor