Showing Compound Aminopterin (FDB022702)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:11 UTC

Update date

2015-10-09 22:30:45 UTC

Primary ID

FDB022702

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aminopterin

Description

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.(PMID 6398629) [HMDB]

CAS Number

54-62-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-amino-4-Deoxypteroylglutamate	HMDB
4-amino-PGA	HMDB
4-Aminofolate	HMDB
4-Aminofolic acid	HMDB
4-Aminopteroylglutamate	HMDB
4-Aminopteroylglutamic acid	HMDB
Aminopterine	HMDB
APGA	HMDB
L-N-[P-[[(2,4-diamino-6-Pteridinyl)methyl]amino]benzoyl]-glutamic acid	HMDB
Pteramina	HMDB
Aminopterin, disodium salt	MeSH, HMDB
Disodium salt aminopterin	MeSH, HMDB
Sodium, aminopterin	MeSH, HMDB
Aminopterin sodium	MeSH, HMDB
2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate	Generator, HMDB
Aminopterin	MeSH
4-Amino-4-deoxypteroylglutamate	hmdb
4-Amino-PGA	hmdb
L-N-[p-[[(2,4-diamino-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	-0.25	ALOGPS
logP	-0.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	2.25	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	219.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	114.98 m³·mol⁻¹	ChemAxon
Polarizability	44.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C19H20N8O5

IUPAC name

2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

InChI Identifier

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)

InChI Key

TVZGACDUOSZQKY-UHFFFAOYSA-N

Isomeric SMILES

NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1

Average Molecular Weight

440.4127

Monoisotopic Molecular Weight

440.15566579

Classification

Description

Belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Folic acids

Alternative Parents

Substituents

Folic acid
Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Aminopyrimidine
Aralkylamine
Secondary aliphatic/aromatic amine
Pyrimidine
Pyrazine
Monocyclic benzene moiety
Benzenoid
Imidolactam
Dicarboxylic acid or derivatives
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Amine
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Primary amine
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location:

Organ and components:

Spleen

Subcellular:

Cytoplasm

Tissue and substructures:

Adipose tissue

Role

Industrial application:

Drug

Environmental role:

Air pollutant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Aminopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0005-2149100000-61d406d05355a4fc3d26	Spectrum
Predicted GC-MS	Aminopterin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-3060950000-0b4e0db1ce895d3cb34e	Spectrum
Predicted GC-MS	Aminopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aminopterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0030900000-3c3d8f183a438cffe34c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006x-0970000000-ddbb8b8c2d06b8da5f92	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00fr-0900000000-dd78e5bb1683a2c0e531	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fu-0322900000-764b96892d5bbce421b1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0953200000-ea1dce8ceb8c57ed0091	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1930000000-5593e0d8e055aa5cdebc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0003900000-8e0519246e877792792b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00r2-0349500000-5275f7af7a7d4fc7d542	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-8971000000-0fe59aca81e98939920d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00bi-0018900000-a0606201fd010f93c94b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-2529300000-3b9e64ec8c7a3bf2727c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-3921000000-34b66517bd8029a4d622	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0280900000-6e94abf6f12994dffe6f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1594000000-111d532a6321012d4554	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0930000000-b75a7510d239fbddc983	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Spectrum