General Information of Drug (ID: DMQ9RBV)

Drug Name
Aminopterin
Synonyms
APGA; Aminopteridine; Aminopterine; Aminopterinum; Aminotrexate; Pteramina; Pteramina [Czech]; A 1784; A-7170;A-Ninopterin; ENT-26079; Kyselina 4-aminolistova; Kyselina 4-aminolistova [Czech]; Kyselina 4-aminopteroylglutamova; Kyselina 4-aminopteroylglutamova [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-diaminopteridin-6-yl)methyl]amino}phenyl)carbonyl]glutamic acid; N-(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid; N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid; 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]; N-(4-(((2,4-Diamino-6-pteridyl)-methyl)amino)benzoyl)-L-glutamic acid; (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
Indication
Disease Entry ICD 11 Status REF
leukaemia 2A60-2B33 Withdrawn from market [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 440.4
Logarithm of the Partition Coefficient (xlogp) -2
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C19H20N8O5
IUPAC Name
(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Canonical SMILES
C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=NC(=N3)N)N
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
InChIKey
TVZGACDUOSZQKY-LBPRGKRZSA-N
Cross-matching ID
PubChem CID
169371
ChEBI ID
CHEBI:22526
CAS Number
54-62-6
UNII
JYB41CTM2Q
DrugBank ID
DB08878
TTD ID
D0D2RN

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Polypeptide deformylase (PDF) TT9SL3Q DEFM_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease leukaemia
ICD Disease Classification 2A60-2B33
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Polypeptide deformylase (PDF) DTT PDF 8.87E-16 -0.54 -0.86
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drug information of Aminopterin, Health Canada, 2007.
2 Loss of folylpoly-gamma-glutamate synthetase activity is a dominant mechanism of resistance to polyglutamylation-dependent novel antifolates in multiple human leukemia sublines. Int J Cancer. 2003 Feb 20;103(5):587-99.
3 Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.