diethyl N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate (CED0176200)

Record Information

Version

1.0

Creation Date

2016-06-03 12:13:52 UTC

Update Date

2026-08-30 23:34:32 UTC

Accession Number

CHEM044428

Identification

Common Name

diethyl N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate

Class

Small Molecule

Description

diethyl N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 510.56 g/mol, diethyl N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamate is a heavy molecule. This organic compound has the chemical formula C24H30N8O5. It is found in or released from drinking water and water supply, specifically drinking water. The recorded exposure route for this substance is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,5-Diethyl (2S)-2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid	Generator
Diethyl methotrexic acid	Generator

Chemical Formula

C₂₄H₃₀N₈O₅

Average Molecular Mass

510.555 g/mol

Monoisotopic Mass

510.234 g/mol

CAS Registry Number

43170-88-3

IUPAC Name

1,5-diethyl (2S)-2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioate

Traditional Name

1,5-diethyl (2S)-2-[(4-{[(4-amino-2-imino-3H-pteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioate

SMILES

[H][C@@](CCC(=O)OCC)(NC(=O)C1=CC=C(C=C1)N(C)CC1=NC2=C(N)NC(=N)N=C2N=C1)C(=O)OCC

InChI Identifier

InChI=1S/C24H30N8O5/c1-4-36-18(33)11-10-17(23(35)37-5-2)29-22(34)14-6-8-16(9-7-14)32(3)13-15-12-27-21-19(28-15)20(25)30-24(26)31-21/h6-9,12,17H,4-5,10-11,13H2,1-3H3,(H,29,34)(H4,25,26,27,30,31)/t17-/m0/s1

InChI Key

MZRRIAJJDAPQRO-KRWDZBQOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1.31	ALOGPS
logP	0.54	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.62	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	183.92 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	156.61 m³·mol⁻¹	ChemAxon
Polarizability	53.72 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0929-0514970000-cc6d0a82e4c260852f30	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-1925500000-32095bb2f006c3530209	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-0911000000-9b267b814ae05b28beea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08fr-1000940000-29c5beeb513e9fca764c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08gs-2122910000-ac28db54b0901bb8dd84	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006y-9635500000-3190148f442d326e737e	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2198.0	Log mg/kg	[1200:3900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Dihydrofolate reductase	P00375	Mus musculus	Predicted (SEA)	2.10193
Click to view 3D structure	Dihydrofolate reductase	P00374	Humans	Predicted (SEA)	12.378
Click to view 3D structure	Dihydrofolate reductase	P00381	Lactobacillus casei	Predicted (SEA)	8.95266
Click to view 3D structure	Dihydrofolate reductase	P00378	Gallus gallus	Predicted (SEA)	4.5931
Click to view 3D structure	Dihydrofolate reductase	Q920D2	Rattus norvegicus	Predicted (SEA)	12.1445
Click to view 3D structure	Dihydrofolate reductase	P00380	Enterococcus faecium	Predicted (SEA)	3.42537
Click to view 3D structure	Dihydrofolate reductase	P16184	Pneumocystis carinii	Predicted (SEA)	11.6774
Click to view 3D structure	Dihydrofolate reductase	P0ABQ4	Escherichia coli (strain K12)	Predicted (SEA)	12.2223
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	P07382	Leishmania major	Predicted (SEA)	4.12601
Click to view 3D structure	Thymidylate synthase	P04818	Humans	Predicted (SEA)	8.40772
Click to view 3D structure	Folylpolyglutamate synthase, mitochondrial	Q05932	Humans	Predicted (SEA)	2.33548
Click to view 3D structure	Thymidylate synthase	C3SWJ7	Escherichia coli	Predicted (SEA)	6.07224
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	Q07422	Toxoplasma gondii	Predicted (SEA)	17.9832
Click to view 3D structure	Thymidylate synthase	P00469	Lactobacillus casei	Predicted (SEA)	9.10836
Click to view 3D structure	Pteridine reductase 1	Q01782	Leishmania major	Predicted (SEA)	2.02408
Click to view 3D structure	Proton-coupled folate transporter	Q96NT5	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	Folate receptor alpha	P15328	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	Reduced folate transporter	P41440	Humans	Predicted (SEA)	4.98235
Click to view 3D structure	Thymidylate synthase	P07607	Mus musculus	Predicted (SEA)	8.79696
Click to view 3D structure	Bifunctional purine biosynthesis protein ATIC	P31939	Humans	Predicted (SEA)	5.60514
Click to view 3D structure	Folate receptor beta	P14207	Humans	Predicted (SEA)	5.91654
Click to view 3D structure	Bifunctional dihydrofolate reductase-thymidylate synthase	Q27783	Trypanosoma brucei brucei	Predicted (SEA)	1.63483
Click to view 3D structure	Pteridine reductase, putative	Q581W1	Trypanosoma brucei	Predicted (SEA)	1.79053
Click to view 3D structure	Solute carrier organic anion transporter family member 1A3	P70502	Rattus norvegicus	Predicted (SEA)	5.0602
Click to view 3D structure	Folylpolyglutamate synthase, mitochondrial	P48760	Mus musculus	Predicted (SEA)	7.62922