2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-2H3)propyl]-3,4,7,8-tetrahydropteridin-4-one

• ChemBase ID: 167538
• Molecular Formular: C9H13N5O3
• Molecular Mass: 239.23122
• Monoisotopic Mass: 239.1018393
• SMILES: [nH]1c(nc2c(c1=O)N=C(CN2)[C@H]([C@@H](O)C)O)N
• Canonical SMILES: C[C@@H]([C@@H](C1=Nc2c(NC1)nc([nH]c2=O)N)O)O
• InChI: InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m0/s1
• InChIKey: FEMXZDUTFRTWPE-DZSWIPIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-^2H₃)propyl]-3,4,7,8-tetrahydropteridin-4-one
• IUPAC Traditional name: 2-amino-6-[(1R,2S)-1,2-dihydroxy(3,3,3-^2H₃)propyl]-7,8-dihydro-3H-pteridin-4-one
• Synonyms: 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-4(3H)-pteridinone; 7,8-Dihydrobiopterin; Dihydrobiopterin; L-erythro-7,8-Dihydrobiopterin; L-erythro-Dihydrobiopterin; 7,8-Dihydro-L-biopterin-d3

Database IDs

• PubChem SID: 162261671
• PubChem CID: 46781302

CALCULATED PROPERTIES

• Acid pKa: 10.809058
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.9538518
• LogD (pH = 7.4): -1.9477357
• Log P: -1.9475005
• Molar Refractivity: 68.3133 cm^3
• Polarizability: 21.955072 Å^3
• Polar Surface Area: 132.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448552

The labelled reduced form of Biopterin. An oxidation product of tetrahydrobiopterin, a naturally occurring cofactor of the aromatic amino acid hydroxylase and is involved in the synthesis of tyrosine and the neurotransmitters dopamine and serotonin. It

REFERENCES

• Shen, R., et al.: Biochim Biophys Acta., 965, 9 (1988)
• Kwon, N.S., et al.: J. Biol. Chem., 264, 20498 (1988)
• Werner, E.R., et al.: Proc. Soc. Exp. Biol. Med., 203, 1 (1988)