2-amino-3-{1H-pyrrolo[2,3-b]pyridin-3-yl}propanoic acid hydrate

• ChemBase ID: 90328
• Molecular Formular: C10H13N3O3
• Molecular Mass: 223.22852
• Monoisotopic Mass: 223.09569129
• SMILES: n1c2c(ccc1)c(c[nH]2)CC(C(=O)O)N.O
• Canonical SMILES: NC(C(=O)O)Cc1c[nH]c2c1cccn2.O
• InChI: InChI=1S/C10H11N3O2.H2O/c11-8(10(14)15)4-6-5-13-9-7(6)2-1-3-12-9;/h1-3,5,8H,4,11H2,(H,12,13)(H,14,15);1H2
• InChIKey: PXDRHYQAIUZKHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-{1H-pyrrolo[2,3-b]pyridin-3-yl}propanoic acid hydrate
• IUPAC Traditional name: 2-amino-3-{1H-pyrrolo[2,3-b]pyridin-3-yl}propanoic acid hydrate
• Synonyms: α-Amino-1H-pyrrolo[2,3-b]pyridine-3-propanoic Acid Hydrate; D,L-Azatryptophan Hydrate; DL-7-Azatryptophan hydrate; 2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid hydrate; 3-(2-Amino-2-carboxyethyl)-1H-pyrrolo[2,3-b]pyridine hydrate; DL-7-Azatryptophan hydrate

Database IDs

• CAS Number: 7303-50-6; 7146-37-4; 7303-50-6,7146-37-4
• MDL Number: MFCD00150525
• PubChem SID: 24890571; 162077148
• PubChem CID: 24801922

CALCULATED PROPERTIES

• Acid pKa: 2.2889085
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.9547148
• LogD (pH = 7.4): -1.9402728
• Log P: -1.9380924
• Molar Refractivity: 53.9985 cm^3
• Polarizability: 21.539085 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Clear to slightly hazy colourless to faint yellow solution at 50mg/ml in 1M hydrochloric aci
• Apperance: White to Off-White Powder
• Melting Point: >260°C (dec.); 259°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant/Store at -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Toronto Research Chemicals - A803575

An unusual alpha-amino acid with a very potent fluorescent activity. Its used as a vehicle for probing the structure and dynamics of protein and peptides.

REFERENCES

• Watts, R., et al.: J. Med. Chem., 49, 7493 (2006)
• El Khattabi, M., et al.: Biochem. J., 409, 193 (2006)