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N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)glutamic acid

HCID 2154
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1236566-87-2
Standard SMILES
Nc1nc(N)c2nc(CNc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)cnc2n1
InChIKey
TVZGACDUOSZQKY-UHFFFAOYSA-N
Molecular formula
C19H20N8O5
Average molar mass
440.4 g/mol
Monoisotopic mass
440.15566577

Overview

Aminopterin Syndrome Sine Aminopterin (ASSA, OMIM 600325) is an embryopathy caused by maternal treatment with the olic acid antagonist aminopterin has been recognized since 1952 when aminopterin was used as an abortifacient. The characteristic phenotype of the children who survived infancy after having been exposed to aminopterin or its methyl derivative, methotrexate, in early pregnancy included a very unusual facies, skull anomalies, and skeletal defects.(OMIM). Aminopterin is an antimetabolite drug used in treatment of cancer and autoimmune diseases. It acts by inhibiting the metabolism of folic acid. - Wikipedia. The effects of the drug on intracellular metabolic processes, due to the inhibitory action on the enzyme dihydrofolate reductase, show that the result of this inhibition is more complex and is not limited to blockade of the reduction of folic acid alone. Although rescue methods are important in prevention of lethal effects of methotrexate, some metabolic pathways are insufficiently rescued, resulting in toxic reactions following methotrexate administration. (A7894)

Names & identifiers

Preferred name
N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)glutamic acid
IUPAC
2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
English name
N-[4-[[(2,4-DiaMino-6-pteridinyl)Methyl]aMino]benzoyl]glutaMic Acid
Molecular formula
C19H20N8O5
Molecular weight
440.41

Names & synonyms

1236566-87-2N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]glutamic acidDTXSID10858993N-(4-(((2,4-Diamino-6-pteridinyl)methyl)amino)benzoyl)glutamic acidRefChem:1091200DTXCID702091844-Aminofolic acid; APGA2-(4-((2,4-DIAMINOPTERIDIN-6-YL)METHYLAMINO)-BENZAMIDO)PENTANEDIOIC ACIDC19H20N8O5N-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)carbonyl]glutamic acidL-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-4-Aminopteroyl-glutamic acid
Show more names
Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-
Aminofolic acid, 4-SR-010000756364-Aminofolate4-Aminopteroyl-<R>glutamic acidNCGC00015038-03143873-72-72-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid4-Aminopteroylglutamate

Database identifiers

Properties

Computed structural properties

XLogP
-2
Topological polar surface area
219 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
12
Rotatable bonds
9
Heavy atoms
32
Formal charge
0
Complexity
674

Experimental & physicochemical properties

Physical DescriptionSolid

Physicochemical properties

storage temp.
Refrigerator
solubility
Methanol
form
Solid
color
Yellow

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Toxicity Summary · 1 item

Aminopterin is an amino derivative of folic acid which binds competitively to the dihydrofolate reductase enzyme to block tetrahydrofolate synthesis. Tetrahydrofolate is essential in the production of purines and pyrimadines, thus it's deficiency results in a reduction of DNA, RNA and protein synthesis.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 1 item

Aminopterin Syndrome Sine Aminopterin (ASSA, OMIM 600325) is an embryopathy caused by maternal treatment with the olic acid antagonist aminopterin has been recognized since 1952 when aminopterin was used as an abortifacient. Aminopterin is an antimetabolite drug used in treatment of cancer and autoimmune diseases.

Applications

UsesN-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]glutamic Acid is an intermediate in the synthesis of Methotrexate (M260675), a folic acid antagonist, used as a antineoplastic and antirheumatic.

Suppliers7 total

BOC Sciences1-631-485-4226; 16314854226 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
Jilin Chinese Academy of Sciences-yanshen Technology18143011203 · [email protected]

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
1236566-87-2、54-62-6
PubChem CID
2154
DTXSID
DTXSID10858993
Nikkaji
J1.107.429D
北京百灵威科技有限公司18210857532 18210857532 · [email protected]