(2S)-2-[(4-aminophenyl)formamido]pentanedioic acid

• ChemBase ID: 70437
• Molecular Formular: C12H14N2O5
• Molecular Mass: 266.24996
• Monoisotopic Mass: 266.09027156
• SMILES: C(=O)([C@H](CCC(=O)O)NC(=O)c1ccc(cc1)N)O
• Canonical SMILES: O=C(c1ccc(cc1)N)N[C@H](C(=O)O)CCC(=O)O
• InChI: InChI=1S/C12H14N2O5/c13-8-3-1-7(2-4-8)11(17)14-9(12(18)19)5-6-10(15)16/h1-4,9H,5-6,13H2,(H,14,17)(H,15,16)(H,18,19)/t9-/m0/s1
• InChIKey: GADGMZDHLQLZRI-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-aminophenyl)formamido]pentanedioic acid
• IUPAC Traditional name: p-aminobenzoyl-L-glutamic acid
• Synonyms: (S)-2-(4-Aminobenzamido)pentanedioic acid; N-(p-Aminobenzoyl)glutamic acid; N-(4-Aminobenzoyl)-L-glutamic acid; N-(4-Aminobenzoyl)-L-glutamic acid; N-p-AMINOBENZOYL-L-GLUTAMIC ACID; N-(p-Aminobenzoyl)-L(+)-glutamic Acid; NSC 71042; N-(4-Aminobenzoyl)-L-glutamic Acid

Database IDs

• CAS Number: 4271-30-1
• EC Number: 224-261-7
• MDL Number: MFCD00042821
• Beilstein Number: 2816320
• PubChem SID: 24890463; 162036155; 24846005
• PubChem CID: 196473

CALCULATED PROPERTIES

• Acid pKa: 2.71569
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.5079138
• LogD (pH = 7.4): -6.564858
• Log P: -0.8644223
• Molar Refractivity: 66.1024 cm^3
• Polarizability: 24.693901 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Light Tan Waxy Solid
• Melting Point: ~175 °C (dec.)
• Optical Rotation: [α]20/D -15.0±0.5°, c = 2% in 0.1 M HCl

Safety Information

• Storage Condition: 0°C; -20°C Freezer, Under Inert Atmosphere
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (T); ≥98% (TLC); 95+%
• Grade: purum
• Empirical Formula (Hill Notation): C12H14N2O5

DETAILS

MP Biomedicals - 02100606

Crystalline

Sigma Aldrich - A0879

Biochem/physiol Actions
N-p-Aminobenzoyl)-L-glutamic acid is a folate catabolite that can be metabolized by bacterial p-aminobenzoate auxotrophs possessing the enzyme p-aminobenzoyl-glutamate hydrolase.

Sigma Aldrich - 07080

Other Notes
TLC standard for the detection of pteroylmonoglutamates1; Component for the preparation of aminopterin2

Toronto Research Chemicals - A593770

Major metabolite of 5-Methyltetrahydrofolic Acid

REFERENCES

• Ng, X., et al.: Food Chem., 110, 1000 (2008)
• Ng, X., et al.: Food Chem., 106, 200 (2008)
• Verlinde, P., et al.: J. Agric. Food Chem., 57, 6803 (2008)
• Gutzeit, D., et al.: Anal. Bioanal. Chem., 391, 211 (2008)