2-amino-6-[(1S,2R)-1,2,3-trihydroxy(1,2,3-13C3)propyl]-4,8-dihydro(6,7-13C2)pteridin-4-one

• ChemBase ID: 175076
• Molecular Formular: C9H11N5O4
• Molecular Mass: 258.17801419
• Monoisotopic Mass: 258.09787805
• SMILES: n1c(nc2c(c1=O)n[13c]([13cH][nH]2)[13C@@H]([13C@@H]([13CH2]O)O)O)N
• Canonical SMILES: O[13CH2][13C@H]([13C@H]([13c]1[13cH][nH]c2c(n1)c(=O)nc(n2)N)O)O
• InChI: InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6+/m1/s1/i1+1,2+1,3+1,4+1,6+1
• InChIKey: BMQYVXCPAOLZOK-NNFFBITRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6-[(1S,2R)-1,2,3-trihydroxy(1,2,3-^1^3C₃)propyl]-4,8-dihydro(6,7-^1^3C₂)pteridin-4-one
• IUPAC Traditional name: 2-amino-6-[(1S,2R)-1,2,3-trihydroxy(1,2,3-^1^3C₃)propyl](6,7-^1^3C₂)-8H-pteridin-4-one
• Synonyms: 2-Amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone-13C5; Neopterin-13C5; 2-Amino-4-hydroxy-6-(1,2,3-trihydroxypropyl)pteridine-13C5; 2-Amino-6-((1S,2R)-1,2,3-trihydroxypropyl)-4(8H)-pteridone-13C5; 6-D-erythro-Neopterin-13C5; D-(+)-Neopterin-13C5; D-erythro-Neopterin-13C5; D-Neopterin-13C5

Database IDs

• PubChem SID: 164230986
• PubChem CID: 46782467

CALCULATED PROPERTIES

• Acid pKa: 7.700993
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -3.252219
• LogD (pH = 7.4): -3.407013
• Log P: -3.249695
• Molar Refractivity: 59.3548 cm^3
• Polarizability: 22.24828 Å^3
• Polar Surface Area: 152.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid
• Apperance: Off-WHite Solid
• Melting Point: >224°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N390007

Labelled precursor in the biosynthesis of Biopterin. First isolated from the pupae of bees.

REFERENCES

• Kobashi, I., et al.: Agric. Biol. Chem., 35, 47 (1971)
• Fukushima, S., et al.: J. Biol. Chem., 247, 4549 (1971)