sodium 4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoate

• ChemBase ID: 155161
• Molecular Formular: C14H12N7NaO2
• Molecular Mass: 333.28055
• Monoisotopic Mass: 333.09501694
• SMILES: c1cc(ccc1C(=O)[O-])NCc1cnc2c(n1)c(nc(n2)N)N.[Na+]
• Canonical SMILES: Nc1nc(N)c2c(n1)ncc(n2)CNc1ccc(cc1)C(=O)[O-].[Na+]
• InChI: InChI=1S/C14H13N7O2.Na/c15-11-10-12(21-14(16)20-11)18-6-9(19-10)5-17-8-3-1-7(2-4-8)13(22)23;/h1-4,6,17H,5H2,(H,22,23)(H4,15,16,18,20,21);/q;+1/p-1
• InChIKey: NDXULQWYAMJQGC-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoate
• IUPAC Traditional name: sodium 4-{[(2,4-diaminopteridin-6-yl)methyl]amino}benzoate
• Synonyms: 4-Amino-4-deoxypteroic acid; 4-(N-[2,4-Diamino-6-pteridinylmethyl]amino)benzoic acid sodium salt

Database IDs

• CAS Number: 100929-45-1
• MDL Number: MFCD00006709
• PubChem SID: 24893425; 162249299
• PubChem CID: 3649384

CALCULATED PROPERTIES

• Acid pKa: 4.723179
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.5940884
• LogD (pH = 7.4): -2.371171
• Log P: 0.25227025
• Molar Refractivity: 97.7253 cm^3
• Polarizability: 30.73599 Å^3
• Polar Surface Area: 155.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (TLC)
• Linear Formula: C14H12N7O2Na

DETAILS

Sigma Aldrich - D1393

Biochem/physiol Actions
4-(N-[2,4-Diamino-6-pteridinylmethyl]amino)benzoic is an impurity found in methotrexate preparations. 4-(N-[2,4-Diamino-6-pteridinylmethyl]amino)benzoic may be used as a reference compound in methothrexate purity analysis.