2-amino-7-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one

• ChemBase ID: 176919
• Molecular Formular: C9H11N5O3
• Molecular Mass: 237.21534
• Monoisotopic Mass: 237.08618924
• SMILES: n1c(nc2c(c1=O)ncc([nH]2)[C@H]([C@@H](O)C)O)N
• Canonical SMILES: C[C@@H]([C@@H](c1cnc2c([nH]1)nc(nc2=O)N)O)O
• InChI: InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-5-7(12-4)13-9(10)14-8(5)17/h2-3,6,15-16H,1H3,(H3,10,12,13,14,17)/t3-,6-/m0/s1
• InChIKey: LNXRKRFGNHXANN-DZSWIPIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one
• IUPAC Traditional name: 2-amino-7-[(1R,2S)-1,2-dihydroxypropyl]-8H-pteridin-4-one
• Synonyms: 2-Amino-7-[(1R,2S)-1,2-dihydroxypropyl]-4(3H)-pteridinone; L-erythro- 1-(2-Amino-4-hydroxy-7-pteridinyl)-1,2-propanediol; 2-Amino-7-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone; 7-Biopterin; Primapterin; L-Primapterin

Database IDs

• CAS Number: 2636-52-4
• PubChem SID: 164232829
• PubChem CID: 5489507

CALCULATED PROPERTIES

• Acid pKa: 7.772067
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.2049139
• LogD (pH = 7.4): -2.3404725
• Log P: -2.202785
• Molar Refractivity: 57.8111 cm^3
• Polarizability: 21.548895 Å^3
• Polar Surface Area: 132.66 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P733000

7-Substituted pterins, a new class of mammalian pteridines. Primapterin, Anapterin, and 6-Oxo-primapterin, three new 7-substituted pterins identified in a patient with hyperphenylalaninemia.

REFERENCES

• Katoh, S., et al.: Life Sci., et al.: 45, 2561 (1989)
• Curtius, H.C., et al.: J. Biol. Chem., 265, 3923 (1989)